Vacation rentals in Ocean Pines, MD with free parking

Explore 361 vacation rentals, homes, and villas with free parking in Ocean Pines, MD for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Family-Friendly Homes and Homes with Pools. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $30 per night and homes offering up to 10 bedrooms and 7 bathrooms, it's easy to book a personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

361 Homes with Free Parking in Ocean Pines

Ocean Pines Chalet

Ocean Pines, MD, US
4 Bedrooms 10 Guests
Aug 30 - Sep 1
$123 night

Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding coastal charm. This delightful retreat is surrounded by a plethora of local amenities including community pools, parks, tennis and basketball courts, skate parks, golf, and a yacht club. A 15-minute drive from the bustling Ocean City beaches, it offers the perfect blend of serene living and beachside excitement, making it an ideal getaway for those seeking both relaxation and adventure ✨ Ocean Pines Chalet Retreat – A-Frame Luxury, In-Law Suite & Outdoor Deck 🌲✨ Welcome to the Ocean Pines Chalet, a stunning A-frame home that blends soaring architecture, coastal charm, and generous space for families or groups. With dramatic 40-foot vaulted ceilings, multiple living areas, and a private in-law suite, this retreat offers comfort, privacy, and relaxation in a serene Ocean Pines setting. ⸻ 🛌 Where You’ll Sleep • Primary Bedroom (main level): King bed, spa-like private bath, desk/vanity space 😴 • Bedroom 2 (2nd floor): King bed, Smart TV, spacious and comfortable 🛏️ • Bedroom 3 (2nds floor): Queen bed, Smart TV, cozy and inviting 🛌 • In-Law Suite (Bedroom 4 - main level): Queen bed, private bath, kitchenette, living area & TV — ideal for guests wanting extra privacy ✨ - Living room includes a Sofa Bed. • Total Beds: 5 🛏️ • Baths: 3 Full Bathrooms 🛁 and Half Bathroom ⸻ 🏠 The Space Main Living Area: Step into an expansive open-concept living space highlighted by breathtaking 40-foot vaulted ceilings and classic A-frame design. The living room and kitchen flow seamlessly, creating a warm gathering space for meals, conversation, and relaxation. Plush seating surrounds a charming fireplace, while large windows fill the home with natural light and showcase tasteful coastal décor. Kitchen: Fully equipped and open to the living area, making it perfect for preparing meals, entertaining, and enjoying time together. In-Law Suite: A private, self-contained retreat featuring a bedroom, full bathroom, kitchenette, and living area with a custom accent wall and TV — perfect for extended stays or multi-generational groups. ⸻ Bring Your Furry Friend! 🐾 We welcome up to 2 dogs per stay. 🌳 Outdoor Living • Spacious deck with comfortable seating • Blackstone grill for outdoor cooking 🍔 • Ideal for morning coffee, al fresco dining, or relaxed evenings surrounded by nature ⸻ 🏊 Ocean Pines Club & Pool Access (Fees Apply) Guests may enjoy access to Ocean Pines community amenities with the purchase of a per-person day pass. 🎟️ One Beach Club Parking Pass is provided for the Ocean Pines Beach Club in Midtown Ocean City on 50th st. This allows you to park by the community pool and have easy access to Ocean City Beaches. 🌊 Available Pools: • 4 outdoor pools • 1 indoor pool 💲 Daily Pool Fees: • Adults: $18 per person • Youth (ages 5–17): $16 per person 🕙 Hours: Most pools are open daily from 10:00 AM – 6:00 PM, with select locations offering extended hours. 📅 Outdoor pools typically operate from Memorial Day through Labor Day, weather permitting. 📌 Fees, hours, and availability are managed by Ocean Pines and are subject to change. ⸻ 📍 Location, Location, Location Perfectly situated in the heart of Ocean Pines, this home offers a peaceful residential escape while keeping you close to dining, shopping, recreation, and coastal attractions. Guests love the balance of quiet neighborhood living with easy access to beaches, marinas, and charming nearby towns. 🚗 Nearby Destinations: • ⛵ Ocean Pines Yacht Club — approx. 5-minute drive, waterfront dining and bay views • 🍔 Southgate Grill — approx. 9-minute drive, casual local favorite • 🌮 Casita Linda — approx. 9-minute drive, popular Mexican cuisine • 🛍️ Pennington Commons — approx. 9-minute drive, shopping and essentials • 🏘️ Berlin, MD — approx. 14-minute drive, charming historic town with boutiques and dining • 🏖️ Ocean City Beach — approx. 15-minute drive, beaches, boardwalk, dining, and entertainment This location truly gives you the best of both worlds — tranquil community living with convenient access to classic coastal fun. ⸻ 🌟 Why Guests Love It • Iconic A-frame architecture with vaulted ceilings • Private in-law suite for flexible group stays • Cozy fireplace and bright open layout • Spacious deck with grill for outdoor enjoyment • Access to Ocean Pines amenities and pools ⸻ 💡 The Perfect Coastal Escape Whether you’re planning a relaxing retreat, a family getaway, or a multi-generational stay, the Ocean Pines Chalet delivers space, comfort, and timeless coastal charm — all in a serene setting close to everything the area has to offer. ⸻ 🧺 STARTER KIT We provide essential linens and a starter supply kit to help you settle in. Please note that these items are not replenished during your stay. 🍽️ Kitchen Kit: - 1 roll of paper towels - 2 small trash bags - 2 large trash bags - Dish soap - 2 dishwasher pods - 2 laundry pods - 1 sponge - 2 dish towels 🚿 Full Bathroom Kit: - 2 rolls of toilet paper per bathroom - Travel-size shampoo, conditioner, body wash, body lotion, and bar soap 🛏️ Linens & Towels: - Beds are made with sheets, pillowcases, shams, and a comforter - Sheets for sofa beds are provided and left in the room with the couch (not provided for trundles or rollaway beds) - Each guest receives 1 towel set (bath towel, hand towel, and washcloth) - A washer and dryer are available for guest use should you wish to refresh towels or linens during your stay Before check-in, guests are required to complete a pre-arrival verification. As part of this process, guests will be asked to choose either a refundable security deposit or a non-refundable damage protection plan option before check-in details are released. Oceans Edge Vacations does not accept or process Affirm payments. If financing options are displayed through VRBO or another booking platform, those programs are administered entirely by the third-party provider and are not supported by our reservation system. The property includes a barbecue grill for guest use; please ensure it is thoroughly cleaned after each use, as a cleaning fee of up to $100 may be applied if the grill is left dirty upon departure. A valid government-issued photo ID is required to verify identity, confirm age, and finalize your booking. Access to the property will not be granted until verification is completed. A rental agreement must be signed prior to your stay. A valid credit card is required to be kept on file for incidentals, damages, or policy violations. Occupancy is limited to the number of guests listed on the reservation. Unauthorized guests or parties are strictly prohibited. Quiet hours are enforced from 10PM-9AM. Excessive noise or disturbances may result in fines or immediate removal from the property without refund. This property may be equipped with exterior security cameras for safety and verification purposes. There are no cameras inside the home. This home is equipped with noise monitoring devices that measure decibel levels only. These devices do not record conversations or audio. No smoking or vaping is permitted inside the home. Evidence of smoking will result in additional cleaning fees. No pets allowed unless explicitly approved. Unauthorized pets will result in additional charges. Guests are responsible for complying with all local laws, HOA rules, and community guidelines. Check-in and check-out times must be adhered to unless otherwise approved. Any violations of these policies may result in additional charges, cancellation of the reservation, or removal from the property without refund. If you need to have a package delivered during your stay please note that our delivery pick up window is Monday-Friday 9am-5pm at our main office. Please reach out to obtain the address that the package would be delivered to. Please note Oceans Edge Vacations is not responsible for packages that are not shipped directly to our office. If you would like to inquire about requesting an early check-in, please note that all early check-in requests are based upon availability. Request are only reviewed 24 hours prior to your check-in date. There is an additional fee of $75 if we can accommodate this request for you. Our calendars do tend to full up rather quickly. If you see a spot open feel free to instantly book. This is a non-smoking unit. Oceans Edge Vacation Rentals charges a $1,000 fine for smoking in the unit. Due to the high volume of turnovers in season and to provide the latest check out possible, cleaners may be completing cleanings until 6PM. Trust & Safety: By booking a stay with us you give permission permission to the property manager to use a third-party to verify my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest verification can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions. We warmly welcome you to our coastal haven and wish to ensure your stay is as enjoyable as possible. However, we kindly remind our guests that certain elements beyond our control, such as weather conditions, nearby construction activities, or the exuberance of neighboring celebrations, may influence your experience. Nestled close to nature’s bounty, our location invites occasional visits from local wildlife, including raccoons, foxes, diverse bird species including seagulls, and an array of insects. While these encounters are part of the natural charm of our setting, we diligently treat our properties to minimize unwanted guests and maintain your comfort. Should you encounter any aspect of nature that feels less than welcoming or experience any issues with appliances, HVAC systems, electrical components, or cleanliness, please do not hesitate to inform us promptly and provide photographic evidence. We require that you allow us the opportunity to rectify the problem during your stay, as our response time is typically less than an hour. We will make every effort to address and resolve the situation to the best of our ability. However, please understand that such natural occurrences or maintenance issues do not warrant refunds. By booking this property you agree and understand no refunds are given. Our commitment is to provide a serene and delightful escape, and we are here to assist in making your experience as pleasant as possible, within the harmony of our natural surroundings.

Waterfront Retreat with Boat Dock

Ocean Pines, MD, US
3 Bedrooms 7 Guests
Aug 30 - Sep 1
$450 night

Escape to Qwack House, a beautiful 3BR/2BA waterfront, pet friendly, retreat in Ocean Pines. Perfect for families, this home features a game room, a huge deck with a BBQ, and a private dock on the canal. Enjoy community amenities like pools, a beach club, and a golf course, all just a short drive from Ocean City beach. Your serene getaway awaits! Welcome to Qwack House, your beautiful waterfront retreat in Ocean Pines! This updated home is the perfect setting for a memorable vacation with family and friends. Key Features: Bedrooms/Bathrooms: 3 bright bedrooms and 2 full bathrooms. Living Space: A modern, fully stocked kitchen opens into the comfortable living areas. A cheerful sunroom offers a perfect spot to relax and watch the ducks on the canal. Game Room: For some friendly competition, the garage has been converted into a game room, complete with a ping pong table and a basketball game. Outdoor Living: Step outside onto the huge deck to enjoy the water views, fire up the BBQ grill for an evening cookout, or head down to your private dock. Guests will have private and exclusive access to the entire home and its amenities. Full Access: You can use the entire house, including all bedrooms, bathrooms, kitchen, and living areas. Private Entrance: Entry is seamless with a smart lock. You will receive a unique door code for your stay, allowing for easy self-check-in. Outdoor Amenities: Full access to the private deck, backyard, BBQ grill, and private boat dock. Game Room: The game room in the garage is fully accessible to guests. To ensure a smooth and enjoyable stay, please note the following: Parking is a breeze with 6 spots for vehicles. Check-In Instructions: Your detailed arrival instructions, including the unique door code for the smart lock, will be sent to you via email in the week leading up to your stay. Required Renter Agreement: Please be aware that the required renter agreement must be signed and returned before we can send the final check-in instructions. Email Delivery: We recommend checking your spam or junk folder if you do not see the email with your arrival information in your primary inbox. License number: 4970

Furnished Deck! Waterfront Ocean Pines Home

Ocean Pines, MD, US
2 Bedrooms 5 Guests
Aug 30 - Sep 2
$333 night

On-Site Bay Access | Patio w/ Al Fresco Dining Area | Great for Families Your bayside retreat awaits at this 2-bedroom + loft, 2-bath vacation rental house in Ocean Pines. You can spend your morning on the private dock or sipping coffee on the deck before heading out to explore. The nearby Ocean City Boardwalk and Fenwick Island State Park are perfect for your next adventure. Afterward, unwind on your patio and enjoy the water views. Book your next getaway today! -- THE PROPERTY -- STR-5741SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed- Bedroom 2: 1 king bed- Loft: 3 twin beds INDOOR LIVING- 2 Smart TVs w/ cable- Dining table- Board games, books OUTDOOR LIVING- Patio- Deck KITCHEN - Stove/oven, refrigerator- Dishware/flatware, cooking basics- Drip coffee maker- Microwave, toaster, blender- Trash bags & paper towels GENERAL - Free WiFi- Central A/C & heating, ceiling fans- Washer/dryer- Linens/towels & hair dryer ACCESSIBILITY- Multi-level home, 12 steps to enter PARKING- Driveway (2 vehicles)- No street parking -- THE LOCATION -- - On-site access to Isle of Wight Bay- 11 miles to Ocean City Boardwalk- 14 miles to Fenwick Island State Park- 9 miles to Baja Amusements- 6 miles to Ocean Downs Casino- 25 miles to Salisbury Regional Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking- No pets allowed- No events, parties, or large gatherings- Additional fees and taxes may apply- Photo ID may be required upon check-in  Additional INFORMATION- This multi-level home requires stairs to enter. it offers bedrooms and full bathrooms on the main level Licence number: STR-5411;STR-5741

Ocean Pines Resort Home with Porch

Ocean Pines, MD, US
3 Bedrooms 6 Guests
Aug 26 - 29
$382 night

Vacation in this private, pet-friendly home in Northside Ocean Pines, with deck and screened in porch. This cozy retreat is perfect for families and friends. Enjoy a spacious layout with a fully equipped kitchen, and a private deck. Just a short walk to Bainbridge Park and close to community pools, the yacht club and a golf course, it’s the ideal resort vacation base. Includes beach pass! Welcome to your private retreat in Northside Ocean Pines! This entire home offers a peaceful escape, nestled within a dense, green forest setting, making it the perfect home base for your coastal vacation. Key Features: Living Area: Clean and cozy large sectional sofa and a wall-mounted TV, perfect for relaxing. Kitchen & Dining: A spacious, fully equipped kitchen and dining area; Keurig 2 in 1 coffee pot (pods or coffee pod) Bedrooms: 3 great sized bedrooms with natural light; King bedroom has an en suite bathroom Bathrooms: Both full bathrooms contain a tub and shower. Outdoor Space: Screened in porch with sectional sofa as well as a deck with outdoor dining table and chairs. A Blackstone 36" grill is available for you to use. Board games, cards etc available for some family fun Pet-Friendly: We welcome you to bring your furry family members along! Parking: Plenty of parking for your group Guests will have private and exclusive access to the entire home, patio, and yard. Entry is seamless and secure with a keyless smart lock. A unique door code will be generated and provided specifically for the duration of your stay, allowing for convenient self-check-in. Rental Agreement: A Guest Form must be signed electronically before your arrival. Check-in Instructions: Once the agreement is signed, detailed arrival instructions and your unique door code will be sent to you via email. Email Confirmation: Please be sure to check your spam or junk folder if you do not see the arrival instructions in your inbox. Security: For your safety and the security of the property, exterior security cameras are present on the premises. Registration: 6043 License number: 6043

2 Mi to Golf: Hot Tub Hideaway in Ocean Pines

Ocean Pines, MD, US
3 Bedrooms 6 Guests
Aug 29 - Sep 2
$334 night

- Great Outdoor Space - Off-Street Parking With a hot tub, large deck, and prime location, this 3-bed, 2-bath vacation rental house in Ocean Pines offers a carefree getaway! When you're not visiting nearby attractions, lounge by the fireplace or prepare snacks in the full kitchen. For an additional fee, enjoy access to the Ocean Pines Beach Club amenities like a pool and tennis courts! -- THE PROPERTY -- SLEEPING ARRANGEMENTS: - Bedroom 1: King Bed - Bedroom 2: King Bed - Bedroom 3: Queen Bed INDOOR LIVING: - Air conditioning, central heating, ceiling fans - 4 Smart TVs (each bedroom & Grand Room) - Gas fireplace - Desk space - Picture windows OUTDOOR LIVING: - Spacious deck - Charcoal grill (charcoal not provided) - Hot tub - Private yard, patio furniture KITCHEN: - Refrigerator, stove/oven, dishwasher - Cooking basics - Coffee maker w/ starter pack of Keurig coffee, pods & creamers GENERAL: - Free WiFi - Washer & dryer - Linens & towels - CD player - Hair dryer OCEAN PINES AMENITIES (w/ additional fees): - Outdoor pool, clubhouse, playground, tennis court ACCESSIBILITY: - Grab rails in the bathroom PARKING: - Driveway (4 vehicles) - Street parking - No garage access -- THE LOCATION -- - 4 miles to Casino at Ocean Downs and Race Track - 7 miles to Baja Amusements - 9 miles to Ocean City Boardwalk & Beach - 23 miles to Salisbury Regional Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties or large gatherings - Additional fees and taxes may occur - A photo ID will be required before check-in. Guests must email the homeowner a copy of their driver's license before arrival - NOTE: Guests are advised to bring their own beach supplies (chairs, towels, cooler, etc) - NOTE: Additional fees apply to use the community amenities. Reach out to the homeowner after booking for more information - NOTE: The garage is not available for guests to use - NOTE: The property comes with a starter kit of one paper towel roll and a roll of toilet paper per restroom

Game Room! Waterfront Group Haven in Ocean Pines

Ocean Pines, MD, US
6 Bedrooms 13 Guests
Aug 29 - 31
$722 night

Game Room | Fire Pit | Pets Welcome w/ Fee | Fishing Access On-Site | Community Amenities w/ Addt'l Fee Experience the best of waterfront living at this Ocean Pines vacation rental! With its stunning views and ample outdoor living space, this 6-bedroom, 4-bath home is an ideal base for a stress-free group getaway. Spend your days fishing or visiting Ocean City's famous beach and boardwalk. Afterward, dine al fresco on the deck and play pool with your crew! -- THE PROPERTY -- STR-4001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed - Bedroom 3: 1 queen bed - Bedroom 4: 2 twin beds - Bedroom 5: 1 queen bed - Bedroom 6: 1 bunk bed (twin/full) COMMUNITY AMENITIES (addt'l fee) - Tennis courts - Pickleball courts - Outdoor pools INDOOR LIVING - Smart TVs w/ cable - Pool table, foosball table, wet bar - Board games, books - Electric fireplaces - En-suite bathrooms, walk-in closet OUTDOOR LIVING - Gas grill - Deck, private yard - Outdoor dining areas, seating - Private hot tub KITCHEN - Refrigerator, stove/oven, dishwasher - Dual drip/single-serve coffee maker - Blender, toaster, microwave - Cooking basics, spices - Trash bags/paper towels GENERAL - Central heating & A/C - Washer/dryer, laundry detergent, iron/board - Linens/towels, complimentary toiletries, hair dryer - Free WiFi FAQ - 4 exterior security cameras (facing out) - Pet fee (paid pre-trip) - Quiet hours (10:00 PM-8:00 AM) - Boat slip/lift not available ACCESSIBILITY - 2-story home, 1 exterior step & interior stairs required to enter PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Convenient location near Ocean Pines Yacht Club & Golf Club - 4 miles to restaurants & 6 miles to Ocean Downs Casino - 11 miles to Ocean City: beach access, boardwalk, Trimper Rides, Jolly Roger at the Pier, shopping, dining - 16 miles to Assateague State Park - 26 miles to Salisbury Regional Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $100 fee (+ fees & taxes) - No events, parties, or large gatherings - Please observe quiet hours from 10:00 PM to 8:00 AM - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires 1 exterior step to enter. Interior stairs are required to access the main and lower levels - Your safety matters. This property features 4 exterior security cameras: 1 camera is located above the side entrance facing the exterior stairs, 1 camera is located on the front of the home facing the driveway, and 2 cameras are located on the back of the home facing the deck and backyard. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion - Community amenities require an additional fee, which may be paid to the HOA on-site upon arrival - The boat slip & lift are not available for guest use Licence number: 4001

Waterfront Getaway with Boat Slip

Ocean Pines, MD, US
3 Bedrooms 8 Guests
Sep 20 - 23
$291 night

Escape to our bright, tranquil canal-front house in Ocean Pines, perfect for large families and groups. This waterfront retreat features a modern kitchen, multiple living areas, a game room, and a private boat slip. Enjoy access to community pools, a private beach club, and a golf course. Comfortably accommodates large groups seeking relaxation and fun. Escape to this stunning and tranquil canal-front house in beautiful Ocean Pines! Flooded with natural light, our home offers a bright and airy coastal retreat perfect for families and groups seeking both relaxation and recreation. The main level features a modern, fully updated kitchen with a large island, perfect for preparing meals together. Relax in one of two distinct living areas, including an upper living room with an 80-inch TV and gaming cord for endless entertainment. Downstairs, you’ll find a fun bar room and a garage complete with a ping pong table. The home includes 3 spacious bedrooms and 3 full bathrooms, with TVs provided in each bedroom for your comfort. To accommodate your group, the following additional sleeping arrangements are also available: 1 Queen sleeper sofa in the upper living room 2 Queen sleeper sofas downstairs 1 two-person Futon downstairs 1 Queen blow-up mattress 2 Twin blow-up mattresses Your waterfront getaway includes full access to the entire home and its fantastic outdoor spaces. Enjoy beautiful views from the large, multi-level deck right on the canal, or unwind in the cozy screened-in porch. Bring your boat and take advantage of the private boat slip available for your exclusive use. As our guest, you will also have access to the wonderful amenities offered by the Ocean Pines community (fees apply) including: Multiple swimming pools Private beach access with an oceanfront pool club A community golf course Access to the Ocean Pines community amenities such as pools and the beach club may require guest passes. Please inquire for more details on obtaining and using these passes on the Ocean Pines Community site License number: 5281

Patio, Pool Access! Coastal Ocean Pines Cottage

Ocean Pines, MD, US
3 Bedrooms 3 Guests
Aug 30 - Sep 1
$175 night

Your charming coastal escape awaits at this 3-bedroom, 1-bathroom vacation rental in Ocean Pines, Maryland! Spend your days lounging on the sandy beach and visiting exciting family attractions, like the Trimper Rides of Ocean City or the Jolly Roger Amusement Park. After browsing through Ocean City Boardwalk's shops, return to the property for a delicious barbecue on the grill. This cottage also features a delightful patio and access to a refreshing community pool. -- THE PROPERTY -- 5249 | Gas Grill (Propane Provided) | Community Kayak & Bicycle Rentals | 11 Mi to Ocean City Beach & Boardwalk Bedroom 1: King Bed | Bedroom 2: Twin Bed | Bedroom 3: Twin Bunk Bed | Living Room: Queen Sleeper Sofa, Twin Sleeper Sofa COMMUNITY AMENITIES: Outdoor pool, basketball court, playground, hiking trail OUTDOOR LIVING: Patio, picnic table w/ umbrella, lounge seating, front porch INDOOR LIVING: 2 flat-screen TVs, 4-person dining table, ceiling fans KITCHEN: Stove/oven, refrigerator, microwave, dishware/flatware, cooking basics, Keurig coffee maker (coffee provided), blender GENERAL: Free WiFi, central air conditioning/heat, complimentary toiletries, towels/linens, iron/board, hair dryer, trash bags/paper towels FAQ: Quiet hours (11:00 PM-6:00 AM) ACCESSIBILITY: Single-story home, exterior steps to enter, 1 interior step required PARKING: Driveway (2 vehicles) -- THE LOCATION -- FAMILY FUN: Ripley's Believe It or Not! (11 miles), Jolly Roger Amusement Park (11 miles), Fun City Arcade (11 miles), Marty's Playland (11 miles), Trimper Rides of Ocean City (11 miles) ATTRACTIONS: Windmill Creek Vineyard & Winery (4 miles), Ocean City, Maryland Visitor Center (11 miles), Ocean City Boardwalk (11 miles), Ocean City Life-Saving Museum (11 miles), Discoversea Shipwreck Museum (14 miles), Fenwick Island State Park (14 miles) BEACHES: Ocean City Beach (11 miles), Maryland Beach (13 miles), Bethany Beach (20 miles) TEE OFF: River Run Golf Club (2 miles), Ocean Pines Golf Club (3 miles), Links at Lighthouse Sound (8 miles) AIRPORT: Salisbury Regional Airport (24 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home requires exterior steps to enter. An interior step is required to access the kitchen, bathroom, and all bedrooms - NOTE: Please observe quiet hours from 11:00 PM to 6:00 AM

Waterfront Cottage w/ Private Dock in Ocean Pines!

Ocean Pines, MD, US
3 Bedrooms 7 Guests
Sep 8 - 11
$377 night

2 Living Areas | BBQ Ready | Community Amenities Access w/ Fee Book your next coastal Maryland getaway at this 3-bedroom, 2-bath vacation rental in Ocean Pines. The cottage features a bright interior with beachy decor, a full kitchen, a private dock where you can launch your own boat, and a community pool just a short walk away. Hit the links at Ocean Pines Golf Club, lounge in the sand at Ocean City Beach, or catch thrills with the kids at Jolly Roger Amusement Park during your stay! -- THE PROPERTY -- STR-5537 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 king bed - Loft: 2 twin beds (convertible to 1 king bed upon request) OCEAN PINES COMMUNITY AMENITIES (addt’l daily fee, paid on-site) - Indoor pool, seasonal outdoor pools - Basketball, tennis & pickleball courts OUTDOOR LIVING - Screened porch w/ dining area - Gas grill (propane provided) - Furnished deck - Private boat dock, water views INDOOR LIVING - 2 living areas, 4 Smart TVs - Dining table, board games KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics, spices - Keurig & drip coffee makers - Microwave, toaster - Dry bar w/ wine cooler GENERAL - Free WiFi - Keyless entry - Central A/C & heating - Linens/towels, iron/board, washer/dryer - Trash bags, paper towels - Hair dryer, complimentary toiletries FAQ - Quiet hours (10:00 PM-8:00 AM) - Local private beach access ACCESSIBILITY - 2-story cottage, 3 steps to enter - 1st-floor bedrooms & full bathroom PARKING - Driveway (3 vehicles) - Boat trailer parking available (1 max) - Street parking prohibited -- THE LOCATION -- - Walk to Ocean Pines Farmers & Artisans Market - Walk to nearby community pool - Near golf courses: Ocean Pines Golf Club, River Run Golf Club, Ocean Resorts Golf Club - 5 miles to Ocean Downs Casino - 9 miles to Ocean City Beach: private access, parking pass provided - 9 miles to Baja Amusements & 11 miles to Jolly Roger Amusement Park - 12 miles to Ocean City Boardwalk - 123 miles to Baltimore/Washington International Thurgood Marshall Airport & 131 miles to Philadelphia International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours from 10:00 PM to 8:00 AM ADDITIONAL INFORMATION - This 2-story cottage requires 3 steps to enter; there are 2 bedrooms and 1 full bathroom on the 1st floor - Street parking is prohibited - Access to the community amenities is available for an additional daily fee, paid on-site - The seasonal community outdoor pools are open Memorial Day-Labor Day - A private block-long beach is available for guest use on 49th St in Ocean City. A parking pass is provided for the nearby lot and can be found inside the property upon arrival Licence number: STR-5537;STR-5537

Park Place | Waterfront Views + Boat Dock

Ocean Pines, MD, US
5 Bedrooms 10 Guests
Sep 7 - 9
$240 night

Welcome to Park Place! This spacious 5-bedroom, 2-bath canal-front retreat offers stunning water views and a bright, inviting layout perfect for families and pets who love life by the water. Enjoy a fully equipped kitchen, boat dock, and exclusive access to Ocean Pines amenities—including a Beach Club parking pass. With nearby beaches, dining, parks, and endless coastal activities, this home is the ideal spot for your Ocean Pines getaway. ✨ Canal-Front Retreat in Ocean Pines – Dock, Deck Views & Beach Club Pass 🌊🐾 Welcome to this spacious canal-front home in Ocean Pines, Maryland, where water views, outdoor living, and family-friendly comfort come together. Perfect for large families or groups, this pet-friendly home offers a private dock, multiple outdoor spaces, and access to Ocean Pines amenities—all just a short drive from Ocean City beaches and attractions. ⸻ 🛌 Where You’ll Sleep Bedroom 1: King bed with TV — spacious and relaxing 😴 Bedroom 2: Queen bed with TV 🛏️ Bedroom 3: Queen bed with TV 🛌 Bedroom 4: Twin bunk bed + trundle with TV — great for kids 🎉 All bedrooms above are located on the main floor level. Bedroom 5: King bed with TV located upstairs in the loft room — perfect for couples or extended family Total Beds: 6 🛌 Baths: 2 full bathrooms 🚿 ⸻ 🏠 The Space This home is designed for comfort, views, and together time. Living Room: Bright and open with large windows, Smart TV, and peaceful canal views—ideal for relaxing after a day out 📺 Enclosed Porch: Dining table seating for six with water views—perfect for meals or board games 🌅 Deck: High-top seating overlooking the canal, great for morning coffee or sunset drinks ⸻ 🍽️ Kitchen & Dining Fully equipped kitchen with everything needed for family meals, including: • Cookware, dishes, and utensils • Blender, coffee maker, and electric hand mixer • Crab Pots for seafood meals • High chair for little guests 📌 Newly renovated kitchen floors add a fresh, modern touch. ⸻ 🌊 Outdoor Living & Waterfront Access Canal-front setting with relaxing water views Private boat dock that accommodates boats up to 25ft — ideal for kayaking or tying up a small boat 🚤 BBQ grill (Charcoal) for outdoor meals 🍔 Large driveway with parking for 4–6 vehicles 🚘🚘🚘🚘 ⸻ 🐶 Pet Friendly Bring Your Furry Friend! 🐾 We welcome up to 2 dogs per stay. To ensure a comfortable experience for all guests, a pet fee of $75 per pet applies. ⸻ 🏊 Ocean Pines Amenities & Beach Club Located in Ocean Pines, guests may enjoy access to community amenities (fees may apply), including: • Community pools 🏊 • Golf course ⛳ • Tennis & basketball courts 🎾 • Kayaking & marinas 🚣 • Playgrounds and walking trails 🌳 🏖️ Bonus: An Ocean Pines Beach Club parking pass is included, providing convenient access to the Ocean Pines Beach Club in Ocean City. Please note that a replacement fee will apply if any Beach Parking Passes are lost or not returned. 📌 Amenities are managed by the Ocean Pines Association, and availability may be seasonal. ⸻ 🚗 Parking Large driveway parking for 4–6 vehicles 🚘 ⸻ 📍 Nearby Attractions 🚗 By Car: ⛵ Ocean Pines Yacht Club — approx. 5 minutes, waterfront dining and marina views 🏖️ Ocean Pines Beach Club — approx. 15 minutes, beachfront access in Ocean City 🎰 Ocean Downs Casino — approx. 10 minutes, gaming, dining, and live entertainment 🏘️ Berlin — approx. 10 minutes, charming downtown shops, dining, and breweries 🌊 Assateague Island National Seashore — approx. 25 minutes, wild horses, beaches, and scenic trails 🎢 Ocean City Boardwalk — approx. 20 minutes, arcades, shops, dining, and classic seaside fun ⸻ 🌟 Guest Favorites Canal-front views & private dock 🌊 Enclosed porch + deck seating 🌅 Pet-friendly home 🐕 Beach Club parking pass included 🏖️ Large driveway for multiple vehicles 🚗 ⸻ 🧰 Extras & Amenities High-speed Wi-Fi 📶 Smart TVs in all bedrooms 📺 Fully equipped kitchen 🍳 Washer & dryer 🧼 Fresh linens and towels 🧺 Starter supply kit included 🧴 ⸻ 💡 Why Guests Love It Guests love this canal-front retreat for its peaceful water views, spacious layout, and access to Ocean Pines and Ocean City attractions. Whether you’re grilling by the water, launching a kayak from the dock, or heading to the beach with the included Beach Club pass, this home offers the perfect balance of relaxation and coastal fun. ⸻ 🧺 STARTER KIT We provide essential linens and a starter supply kit to help you settle in. Please note that these items are not replenished during your stay. 🍽️ Kitchen Kit: - 1 roll of paper towels - 2 small trash bags - 2 large trash bags - Dish soap - 2 dishwasher pods - 2 laundry pods - 1 sponge - 2 dish towels 🚿 Full Bathroom Kit: - 2 rolls of toilet paper per bathroom - Travel-size shampoo, conditioner, body wash, body lotion, and bar soap 🛏️ Linens & Towels: - Beds are made with sheets, pillowcases, shams, and a comforter - Sheets for sofa beds are provided and left in the room with the couch (not provided for trundles or rollaway beds) - Each guest receives 1 towel set (bath towel, hand towel, and washcloth) - A washer and dryer are available for guest use should you wish to refresh towels or linens during your stay Before check-in, guests are required to complete a pre-arrival verification. As part of this process, guests will be asked to choose either a refundable security deposit or a non-refundable damage protection plan option before check-in details are released. Oceans Edge Vacations does not accept or process Affirm payments. If financing options are displayed through VRBO or another booking platform, those programs are administered entirely by the third-party provider and are not supported by our reservation system. Trundle beds and pull-out sofas are provided as optional sleeping spaces. Linens are not provided for these beds, so please plan accordingly if you intend to use them. The property includes a barbecue grill for guest use; please ensure it is thoroughly cleaned after each use, as a cleaning fee of up to $100 may be applied if the grill is left dirty upon departure. A valid government-issued photo ID is required to verify identity, confirm age, and finalize your booking. Access to the property will not be granted until verification is completed. A rental agreement must be signed prior to your stay. A valid credit card is required to be kept on file for incidentals, damages, or policy violations. Occupancy is limited to the number of guests listed on the reservation. Unauthorized guests or parties are strictly prohibited. Quiet hours are enforced from 10PM-9AM. Excessive noise or disturbances may result in fines or immediate removal from the property without refund. This property may be equipped with exterior security cameras for safety and verification purposes. There are no cameras inside the home. This home is equipped with noise monitoring devices that measure decibel levels only. These devices do not record conversations or audio. No smoking or vaping is permitted inside the home. Evidence of smoking will result in additional cleaning fees. No pets allowed unless explicitly approved. Unauthorized pets will result in additional charges. Guests are responsible for complying with all local laws, HOA rules, and community guidelines. Check-in and check-out times must be adhered to unless otherwise approved. Any violations of these policies may result in additional charges, cancellation of the reservation, or removal from the property without refund. If you need to have a package delivered during your stay please note that our delivery pick up window is Monday-Friday 9am-5pm at our main office. Please reach out to obtain the address that the package would be delivered to. Please note Oceans Edge Vacations is not responsible for packages that are not shipped directly to our office. If you would like to inquire about requesting an early check-in, please note that all early check-in requests are based upon availability. Requests are only reviewed 24 hours prior to your check-in date. There is an additional fee of $75 if we can accommodate this request for you. Our calendars do tend to full up rather quickly. If you see a spot open feel free to instantly book. Due to the high volume of turnovers in season and to provide the latest check out possible, cleaners may be completing cleanings until 6PM. Trust & Safety: By booking a stay with us you give permission to the property manager to use a third-party to verify my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest verification can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions. We warmly welcome you to our coastal haven and wish to ensure your stay is as enjoyable as possible. However, we kindly remind our guests that certain elements beyond our control, such as weather conditions, nearby construction activities, or the exuberance of neighboring celebrations, may influence your experience. Nestled close to nature’s bounty, our location invites occasional visits from local wildlife, including raccoons, foxes, diverse bird species including seagulls, and an array of insects. While these encounters are part of the natural charm of our setting, we diligently treat our properties to minimize unwanted guests and maintain your comfort. Should you encounter any aspect of nature that feels less than welcoming or experience any issues with appliances, HVAC systems, electrical components, or cleanliness, please do not hesitate to inform us promptly and provide photographic evidence. We require that you allow us the opportunity to rectify the problem during your stay, as our response time is typically less than an hour. We will make every effort to address and resolve the situation to the best of our ability. However, please understand that such natural occurrences or maintenance issues do not warrant refunds. By booking this property you agree and understand no refunds are given. Our commitment is to provide a serene and delightful escape, and we are here to assist in making your experience as pleasant as possible, within the harmony of our natural surroundings. Pool Access: Please note the community pools are managed by the building and not by us as hosts. Pool availability may be seasonal and is not guaranteed to be open during your stay, as closures can occur for maintenance, repairs, or at the end of the season. License number: 1148

Ocean Pines 3BR House Resort Community

Ocean Pines, MD, US
3 Bedrooms 6 Guests
Aug 26 - 28
$303 night

Escape to this private, pet-friendly home in Northside Ocean Pines, nestled in a peaceful forest setting. This cozy retreat is perfect for families and friends. Enjoy a spacious layout with a sunroom, a fully equipped kitchen, and a private patio with a fire pit. Just a short walk to Bainbridge Park and close to community pools and a golf course, it’s the ideal coastal vacation base. Welcome to your private retreat in Northside Ocean Pines! This entire home offers a peaceful escape, nestled within a dense, green forest setting, making it the perfect home base for your coastal vacation. Key Features: Living Area: Clean and cozy with two comfortable sofas and a large wall-mounted TV, perfect for relaxing. Kitchen & Dining: A spacious, fully equipped kitchen and dining area featuring a convenient breakfast bar and pantry. Sunroom: A beautiful sunroom in the rear of the home boasts a vaulted ceiling and skylights, flooding the space with natural light. Bedrooms: Each bedroom is equipped with a ceiling fan for your comfort. Bathrooms: Both full bathrooms contain a tub/shower combination. Outdoor Space: A private stone paver patio where you can gather around in comfortable Adirondack chairs. A charcoal BBQ grill is also available for your use. Pet-Friendly: We welcome you to bring your furry family members along! Parking: Plenty of parking for your group Guests will have private and exclusive access to the entire home, patio, and yard. Entry is seamless and secure with a keyless smart lock. A unique door code will be generated and provided specifically for the duration of your stay, allowing for convenient self-check-in. Rental Agreement: A rental agreement must be signed electronically before your arrival. Check-in Instructions: Once the agreement is signed, detailed arrival instructions and your unique door code will be sent to you via email. Email Confirmation: Please be sure to check your spam or junk folder if you do not see the arrival instructions in your inbox. Security: For your safety and the security of the property, exterior security cameras are present on the premises. License number: 5199

9 Mi to Beach! Family Getaway in Ocean Pines

Ocean Pines, MD, US
2 Bedrooms 4 Guests
Aug 30 - Sep 1
$131 night

Experience the charm of Ocean Pines in this beautifully appointed 2-bedroom, 1-bathroom vacation rental! The home is complete with an inviting living area, a fully equipped kitchen, and a cozy fireplace. Spend your day lounging at the beach, making a splash in the community pool, or teeing up at the Ocean Pines Golf Club. Perfect for couples and small families and offering optional resort-style perks, this charming property is the quintessential coastal retreat you've been searching for! -- THE PROPERTY -- 5207 | Community Amenities w/ Fee | Fully Equipped Kitchen | Family Friendly Bedroom 1: Queen Bed | Bedroom 2: Twin Bunk Bed OCEAN PINES COMMUNITY AMENITIES (w/ fee, paid on-site): 4 indoor & outdoor pools, tennis & pickleball courts, platform tennis, 18-hole golf course, clubhouse, playgrounds HOME HIGHLIGHTS: Smart TV, fireplace (wood not provided), washer/dryer, deck KITCHEN: Fridge, stove, dishwasher, drip coffee maker (coffee not provided), microwave, cooking basics, dishware/flatware, trash bags/paper towels GENERAL: Free WiFi, keyless entry, central heating & A/C, linens/towels, ceiling fans, iron/board ACCESSIBILITY: Single-story home, stairs required to enter PARKING: Gravel driveway (up to 4 vehicles), RV/trailer parking allowed -- THE LOCATION -- BEACH DAY: Surf Ave Beach (9 miles), Ocean City Beach (9 miles), Maryland Beach (12 miles), State Line Beach (12 miles), Assateague Island Park (13 miles), Bethany Beach (19 miles), Rehoboth Beach (30 miles) FAMILY FUN: Worcester County Public Library (2 miles), Ocean Pines Sports Core Pool (2 miles), Ocean Pines Racquet Center (2 miles), Baja Amusements (7 miles), Trimper’s Rides (8 miles), Ocean City Boardwalk (8 miles), Ripley’s Believe It or Not (8 miles), Jolly Roger Amusement Park (9 miles) TEE TIME: Ocean Pines Golf Club (3 miles), Ocean Resorts Golf Club (3 miles), River Run Golf Club & Community (4 miles), Glen Riddle Golf Club (5 miles), Links At Lighthouse Sound (7 miles) AREA ATTRACTIONS: Ocean Pines Yacht Club (3 miles), Ocean Downs Casino (3 miles), Grand Prix Amusements (7 miles), Paradise Watersports (7 miles), Ocean City Fishing Pier (9 miles) AIRPORT: Salisbury Regional Airport (24 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home requires exterior stairs to enter - NOTE: The community amenities are located at the Ocean Pines Sports Core Pool and Ocean Pines Racquet Center. There is an additional on-site fee to access the amenities - NOTE: The driveway can accommodate 4 vehicles, or 2 vehicles plus an RV/trailer

Canal Front Golf Retreat w/Dock

Ocean Pines, MD, US
3 Bedrooms 6 Guests
Aug 26 - 29
$351 night

Waterfront 3BR/2BA townhome with stunning canal & golf course views in Ocean Pines. This pet-friendly retreat is perfect for golfers, boaters & beach lovers. Enjoy a spacious layout, two patios, and access to 5 pools, tennis courts, and the exclusive Ocean Pines Beach Club. Comfortably accommodates families and groups in a serene, resort-style community. Welcome to your waterfront retreat, a spacious, multi-level 3-bedroom, 2-bathroom townhome filled with ample natural light. The main living area boasts high, wood-beamed ceilings, creating an open and airy atmosphere. Enjoy your morning coffee or an evening cocktail from the patios on both levels, overlooking the serene canal. The home’s layout is designed for comfort and convenience: Upstairs Level: You’ll find the main living room, dining area, a full kitchen, a bedroom with a queen bed, and a full bathroom. Step out onto the open-air patio to soak in the incredible water views. Downstairs Level: This level hosts two additional bedrooms, a second full bathroom, a cozy den, and a laundry area for your convenience. Guests will have private access to the entire townhome, including all rooms, two patios, and the laundry area. Your arrival will be simple and seamless with a smart lock on the front door; you will receive a unique, private code for your stay. Guests are also welcome to use the private dock for boats. To ensure you receive your access code, please complete the rental agreement that will be emailed to you after booking. To ensure a smooth and seamless check-in process, please be aware of the following: A rental agreement will be emailed to you after your booking is confirmed. Signing this rental agreement is required to receive your final check-in instructions and unique door code. Once signed, your check-in instructions will be sent automatically during the week before your stay. We recommend checking your inbox and spam folder for this important email. License number: 4834

Coastal Chic Retreat

Ocean Pines, MD, US
3 Bedrooms 6 Guests
Aug 26 - 28
$106 night

PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Escape to our coastal chic beach retreat! This charming home features 3 bedrooms, 2 bathrooms, and a serene ambiance. With modern decor and comfortable furnishings, it’s the perfect getaway. Just a short 15-minute drive to Ocean City, MD, you’ll have easy access to sandy beaches and vibrant attractions. Book your stay now and indulge in coastal bliss! ✨ Coastal Chic Beach Retreat – Stylish Living, Outdoor Space & Ocean Pines Amenities 🌲🏖️ Welcome to Coastal Chic Beach Retreat, a beautifully designed 3-bedroom, 2-bath home located in the desirable Ocean Pines community. With a bright open layout, coastal-inspired décor, and a peaceful outdoor space, this home is perfect for families or groups looking to relax while staying close to beaches, dining, and local attractions. ⸻ 🛌 Where You’ll Sleep Primary Bedroom: Queen bed — en-suite bathroom and ample storage 😴 Bedroom 2: Queen bed — cozy and inviting 🛏️ Bedroom 3: Two single beds — great for kids or additional guests 🎉 Total Beds: 4 🛌 Baths: 2 full bathrooms 🚿 ⸻ 🏠 The Space Step into a bright, open-concept living area that connects the living room, dining space, and kitchen—ideal for spending time together. Living Room: Plush seating and a flat-screen TV, perfect for movie nights or unwinding after a beach day 📺 Dining Area: Stylish table seating for six, great for family meals or game nights Kitchen: Fully equipped with modern appliances, sleek countertops, and plenty of storage for home-cooked meals 🍳 ⸻ 🍽️ Kitchen & Dining Modern kitchen stocked with cookware, utensils, and essentials Dining table accommodates six comfortably for shared meals ⸻ 🌿 Outdoor Living Private patio with outdoor seating — perfect for morning coffee or evening relaxation ☕ Backyard space for outdoor activities and laid-back gatherings 🌞 ⸻ 🏊 Pool Access Community pool access is available to guests. 🗓️ The pool is typically open from Memorial Day through Labor Day, though it may open earlier or remain open later weather permitting, at the discretion of the community. 📌 Availability is not guaranteed—please feel free to ask if you’d like confirmation of pool access during your stay 😊 ⸻ 🏊 Community Amenities Guests may enjoy access to community amenities (fees may apply), including: • Community pools 🏊 • Golf course ⛳ • Tennis & pickleball courts 🎾 • Parks, walking trails, and playgrounds 🌳 • Marina and waterfront dining ⚓ 📌 Amenities are managed by the Ocean Pines Association and availability may be seasonal. ⸻ 🚗 Parking Private driveway parking available 🚘 📌 Space for multiple vehicles ⸻ 📍 Nearby Attractions 🚗 By Car: 🏖️ Ocean Pines Beach Club — approx. 13 minutes, beachfront access in Ocean City 🎰 Ocean Downs Casino — approx. 8 minutes, gaming, dining, and live entertainment 🏘️ Berlin — approx. 10 minutes, charming downtown shops, restaurants, and galleries 🌊 Assateague Island National Seashore — approx. 20 minutes, wild horses, beaches, and scenic trails 🎢 Ocean City Boardwalk — approx. 15 minutes, arcades, shops, dining, and classic seaside fun 🍽️ Local dining, seafood spots, shopping, and boating adventures just minutes away ⸻ 🌟 Guest Favorites Open-concept living space ☀️ Peaceful patio and backyard 🌿 Coastal décor and natural light 🌊 Seasonal pool access 🏊 Easy drives to beaches and attractions 🚗 ⸻ 🧰 Extras & Amenities High-speed Wi-Fi 📶 Washer & dryer 🧼 Air conditioning ❄️ Fully equipped kitchen 🍳 Fresh linens and towels 🧺 Starter toiletries included 🧴 ⸻ 💡 Why Guests Love It Guests love Coastal Chic Beach Retreat for its stylish coastal design, comfortable layout, and quiet Ocean Pines setting. With access to community amenities, seasonal pool access, and easy drives to beaches and attractions, it’s an ideal home base for a relaxing and memorable coastal getaway. ⸻ 🧺 STARTER KIT We provide essential linens and a starter supply kit to help you settle in. Please note that these items are not replenished during your stay. 🍽️ Kitchen Kit: - 1 roll of paper towels - 2 small trash bags - 2 large trash bags - Dish soap - 2 dishwasher pods - 2 laundry pods - 1 sponge - 2 dish towels 🚿 Full Bathroom Kit: - 2 rolls of toilet paper per bathroom - Travel-size shampoo, conditioner, body wash, body lotion, and bar soap 🛏️ Linens & Towels: - Beds are made with sheets, pillowcases, shams, and a comforter - Sheets for sofa beds are provided and left in the room with the couch (not provided for trundles or rollaway beds) - Each guest receives 1 towel set (bath towel, hand towel, and washcloth) - A washer and dryer are available for guest use should you wish to refresh towels or linens during your stay Check in DIRECTLY AT PROPERTY, NO STOPPING AT A RENTAL OFFICE, Keyless Entry. Before check-in, guests are required to complete a pre-arrival verification. As part of this process, guests will be asked to choose either a refundable security deposit or a non-refundable damage protection plan option before check-in details are released. Oceans Edge Vacations does not accept or process Affirm payments. If financing options are displayed through VRBO or another booking platform, those programs are administered entirely by the third-party provider and are not supported by our reservation system. A valid government-issued photo ID is required to verify identity, confirm age, and finalize your booking. Access to the property will not be granted until verification is completed. A rental agreement must be signed prior to your stay. A valid credit card is required to be kept on file for incidentals, damages, or policy violations. Occupancy is limited to the number of guests listed on the reservation. Unauthorized guests or parties are strictly prohibited. Quiet hours are enforced from 10PM-9AM. Excessive noise or disturbances may result in fines or immediate removal from the property without refund. This property may be equipped with exterior security cameras for safety and verification purposes. There are no cameras inside the home. This home is equipped with noise monitoring devices that measure decibel levels only. These devices do not record conversations or audio. No smoking or vaping is permitted inside the home. Evidence of smoking will result in additional cleaning fees. No pets allowed unless explicitly approved. Unauthorized pets will result in additional charges. Guests are responsible for complying with all local laws, HOA rules, and community guidelines. Check-in and check-out times must be adhered to unless otherwise approved. Any violations of these policies may result in additional charges, cancellation of the reservation, or removal from the property without refund. If you need to have a package delivered during your stay please note that our delivery pick up window is Monday-Friday 9am-5pm at our main office. Please reach out to obtain the address that the package would be delivered to. Please note Oceans Edge Vacations is not responsible for packages that are not shipped directly to our office. If you would like to inquire about requesting an early check-in, please note that all early check-in requests are based upon availability. Request are only reviewed 24 hours prior to your check-in date. There is an additional fee of $75 if we can accommodate this request for you. Our calendars do tend to full up rather quickly. If you see a spot open feel free to instantly book. This is a non-smoking unit. Oceans Edge Vacations charges a $1,000 fine for smoking in the unit. Due to the high volume of turnovers in the peak summer season and to provide the latest checkout possible, cleaners may be completing cleanings until 6 PM. Trust & Safety: By booking a stay with us, you give permission to the property manager to use a third party to verify my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest verification can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions. We warmly welcome you to our coastal haven and wish to ensure your stay is as enjoyable as possible. However, we kindly remind our guests that certain elements beyond our control, such as weather conditions, nearby construction activities, or the exuberance of neighboring celebrations, may influence your experience. Nestled close to nature’s bounty, our location invites occasional visits from local wildlife, including raccoons, foxes, diverse bird species including seagulls, and an array of insects. While these encounters are part of the natural charm of our setting, we diligently treat our properties to minimize unwanted guests and maintain your comfort. Should you encounter any aspect of nature that feels less than welcoming, please do not hesitate to inform us promptly so we can address the situation to the best of our ability. However, we appreciate your understanding that such natural occurrences do not warrant discounts on your stay. Our commitment is to provide a serene and delightful escape, and we are here to assist in making your experience as pleasant as possible, within the harmony of our natural surroundings. Pool open Memorial-Labor Day. Sometimes earlier or later weather permitting at the discretion of the building. Please ask if you are curious about pool openings during your stay :)

Ocean Pines 2BR 1BA Cottage with Fire Pit

Ocean Pines, MD, US
2 Bedrooms 6 Guests
Aug 27 - 29
$283 night

Escape to this stylish, pet-friendly A-frame cottage in a peaceful wooded setting. Perfect for up to 6 guests, this unique sanctuary features a modern kitchen, private deck, and fire pit. Enjoy access to community pools and the beach, all while being a short drive from local dining and golf. A cozy, contemporary retreat with fantastic amenities awaits you. Discover your own quiet sanctuary in this stylish, pint-sized A-frame cottage. The unique architecture, with its high, wood-beamed ceilings, creates a cozy yet modern atmosphere perfect for a getaway. This home comfortably accommodates up to 6 guests, with a recommendation of no more than 4 adults. Key Features: Living Area: A comfortable living room and dining table, perfect for relaxing after a day of exploring. Kitchen: A full, contemporary kitchen equipped with stainless steel appliances, a dishwasher, and everything you need to prepare a delicious meal. Outdoor Space: Enjoy your private deck with seating, or gather around the gravel patio’s fire pit in the evening. A grill is also provided. Amenities: For your convenience, the cottage includes a washer and dryer, yard games, and pickleball equipment. Guests will enjoy complete and private access to the entire A-frame cottage. Our seamless self check-in system features a smart lock for your convenience and security. Your private access includes: The entire home and all its interior amenities. A private deck with outdoor seating. A gravel patio with a fire pit and grill. As our guest, you also have full access to the fantastic community amenities, including: Multiple swimming pools - fees to access Community beach access Pet-Friendly: This is a pet-friendly property. We welcome well-behaved pets with a $50 per pet fee Check-In: This home is equipped with a smart lock for easy, keyless self check-in. Your unique access code will be provided prior to your arrival. Provided beach access pass for your stay starting in May, allows parking for one car at the Beach (no access to club). Ocean Pines has so many options for you to enjoy your vacation. Yacht Club, 5 community pools, golf course. Please check out the Ocean Pines Community site for details on pool and amenity fees License number: 5435

Ocean Serenity - Peaceful, Private Home near Ocean City & Assateague Beaches

Ocean Pines, MD, US
3 Bedrooms 8 Guests
Aug 26 - 29
$360 night

New Property Listing for 2026!!! ★★ Things to Know ★★ ✹ Must be 25+ to rent and stay - no graduating HS groups. ✹ Parking: 4 cars in private driveway, plus street parking. ✹ Pool: There is a communal pool access at this property. ★★ Things to Love ★★ ✹ LINENS & BATH TOWELS INCLUDED! ✹ Peaceful backyard deck surrounded by trees and greenery. ✹ Bayside calm with quick access to Ocean City Boardwalk. ✹ Family‑friendly layout with bunk room and space for up to 8 guests. Wake up to the birdsong and sound of rustling trees in Ocean Serenity located at 27 Gatehouse Trail, Ocean Pines, MD, a private, single-story home tucked into the peaceful, tree-lined community of Ocean Pines, Maryland. A wooded retreat with a backyard deck surrounded by lush greenery. You’ll enjoy the best of both worlds: calm and quiet when you want it and an easy access to the energy of Ocean City’s famous Boardwalk about a 13‑minute drive away. Spend your summer vacation exploring Ocean City MD landmarks at your own pace. You can head to Jolly Roger Amusement Park, just a 15‑minute drive (9.4 miles), where rides and water slides keep the whole family entertained. For a change of scenery, make your way to Assateague Island National Seashore, about a 20‑minute drive (13.8 miles), where wild ponies roam the beaches. After a day of rides, wildlife, or beach fun, you’ll return to the calm of Ocean Pines. The updated interiors and family‑friendly sleeping arrangements make it easy for groups of friends or families to relax together. The open and bright layout of the house is designed for groups who want to enjoy being together. The living area sets the tone and invites everyone to unwind with a comfortable sofa and a relaxed atmosphere, perfect for gathering with a group family or friends. The dining room features a solid wood dining table with matching chairs, offering plenty of space for family meals, card/board or puzzle games. The well-equipped kitchen is designed for simplicity and ease, has everything you need to cook in, including a drip coffee maker ready for your favorite brew — and we’ve stocked a starter kit of essentials so you can settle in the moment you arrive. With sleeping space for up to 8 guests, one bedroom features a queen bed, another offers both a double and a single bed, and the third provides a bunk bed with a trundle, perfect for kids or extra guests. This Ocean Pines MD home blends comfort and coastal charm, perfect for families or friends, another reason guests come back to Ocean City Vacation Homes year after year. From the moment you arrive, Ocean City Vacation Homes wants you to feel at home. That’s why we provide a complimentary starter kit with essentials for your stay. The kit includes body soap, shampoo, toilet paper, paper towels, dish soap, laundry detergent, dishwasher pods, and a sponge — everything you need to get settled in right away. All linens and bath towels are included with your stay, and every bed will be freshly made before you arrive. ★★ Sleeping Arrangements ★★ ✹ Bedroom 1: Queen bed ✹ Bedroom 2: Double bed and single bed ✹ Bedroom 3: Bunk bed with trundle ✹ Occupancy: Sleeps up to 8 guests ★★ Frequently Asked Questions ★★ Do you provide linens and towels? ✹ Yes. All linens and bath towels are included, and every bed is made prior to arrival. ✹ For your stay, 8 bath towels, 4 hand towels and 4 wash cloths are provided. Is parking available? ✹ There are 4 parking spaces. Private driveway and additional street parking. Does this property have a pool? ✹ Yes, there is a communal poo access which opens seasonally from Memorial Day weekend to Labor day weekend. When are lifeguards on duty at the beach? ✹ Ocean City lifeguards are on duty from Memorial Day weekend through mid-September. Is there a coffee maker provided, and if so what kind? ✹ Yes. A drip coffee maker is provided. Just bring your favorite ground coffee and filters. Is the property air-conditioned/heated? ✹ Yes. The house has central air conditioning. Heating is available. Is beach gear provided? ✹ No, beach gear is not included. Is there cable TV? Are there Smart TVs? ✹ Yes, TV is provided. Smart TV availability is not confirmed. Are pets allowed? ✹ No, pets are not permitted at this property. Is smoking allowed anywhere? ✹ No, smoking and vaping are not permitted inside the house or on the balcony. What is the check-in and check-out time? ✹ Check-in begins at 4:00 PM and check-out is by 10:00 AM. ✹ Early check-in may be available between 1:00 PM and 3:00 PM for an additional priority cleaning fee. Please inquire after booking. ✹ Late Check-out may be available between 11:00 AM and 1:00 PM for an additional priority cleaning fee. Please inquire after booking. What is the minimum age to rent? ✹ Guests must be at least 25 years old to book and must be present for the entire stay. Sorry, we do not rent to Senior Week or similar student groups. Parents cannot rent on behalf of children under 25. How do I access the property? ✹ We utilize an E-Lock system for easy, contactless check-in. You will receive your unique access code prior to arrival. What is included in the complimentary starter kit? ✹ Body soap, shampoo, toilet paper, paper towels, dish soap, laundry detergent, dishwasher pods, and a sponge. ★★ Nearby Attractions & Activities ★★ ✹ Beach Access – 13‑minute drive (7.9 miles) ✹ Ocean City Boardwalk – 14‑minute drive (8.0 miles) ✹ Assateague Island – 20‑minute drive (13.8 miles) ✹ Jolly Roger Amusement Park – 15‑minute drive (9.4 miles) ✹ Northside Park – 16‑minute drive (10.8 miles) ✹ North Bus Stop – Ocean Pines Sports Core Pool – 4‑minute drive (1.5 miles) ✹ South Bus Stop – Ocean Pines Sports Core Pool – 4‑minute drive (1.5 miles) ★★ Closest Restaurants & Stores ★★ ✹ Pines Public House & Eatery – 4‑minute drive (1.2 miles) ✹ Southgate Grill – 3‑minute drive (1.0 mile) ✹ Casita Linda Mexican Café – 3‑minute drive (1.1 miles) ✹ Paul and Vinny’s Pizza – 4‑minute drive (1.5 miles) ✹ Food Lion Grocery Store – 4‑minute drive (1.1 miles) ★★ Important Notices ★★ We’re delighted to welcome you to one of our vacation homes and want your stay to be as enjoyable as possible. Please keep in mind that beach life sometimes brings shifting weather, town celebrations, or nearby construction. You may also encounter local wildlife such as seagulls, raccoons, foxes, or the occasional bug. Our homes are treated regularly, but a touch of the outdoors is part of Ocean City’s natural charm. If something feels off — whether it’s an appliance not working correctly or an unexpected maintenance issue — please let us know right away. A quick photo helps, and our team typically responds promptly to resolve anything with as little disruption as possible. While these types of issues don’t qualify for refunds, we’ll always do our best to make your stay smooth. After booking you will be asked to complete a check-in form. This form includes providing your name, birthday, photo ID, and signing rental lease agreement. All rentals include our full linen and towel package. Every bed will be made before you arrive, and each guest receives one bath towel along with fresh sheets and pillowcases. Please respect the home as if it were your own. An additional $500 excessive cleaning fee may apply if the property is left in unacceptable condition, such as requiring cleanup of vomit or urine. Ocean City has adopted a noise control ordinance that makes it unlawful to cause or permit noise levels that exceed those established by the Department of the Environment of the State of Maryland (COMAR 26.02.03.02) or that violate Chapter 30, Article V of the Town Code. It shall be a violation of this agreement and grounds for eviction under Maryland law if these noise levels are exceeded as a result of activity on this property. Ocean City has other noise ordinances, which are criminal offenses if violated. ❗Each property has its own set of house rules. Completing your booking confirms your agreement to follow them. Failure to comply may result in fines or removal without refund.❗ License number: 101567

Spacious Waterfront Home with OC Skyline Views

Ocean City, MD, US
4 Bedrooms 12 Guests
Aug 30 - Sep 2
$354 night

Welcome to our stunning waterfront retreat with panoramic views of the Ocean City skyline! This large and luxurious home offers the perfect blend of comfort, style, and serenity for your next getaway. With four bedrooms, three bathrooms, and the capacity to sleep 12 adults comfortably, it’s an ideal destination for families, friends, or colleagues seeking a memorable escape. As you step inside, you’ll be greeted by a spacious and beautifully decorated living area, where natural light floods the space, highlighting the tasteful furnishings and coastal-inspired decor. The fully-equipped kitchen is a chef’s dream, featuring modern appliances and ample counter space, making it easy to whip up delicious meals for your group. The highlight of this property is undoubtedly the breathtaking waterfront views visible from almost every communal room. Imagine waking up to the sight of the sun rising over the ocean or enjoying a relaxing evening on the enclosed porch, sipping your favorite drink as you watch the city lights twinkle in the distance. For those who appreciate outdoor living, this home boasts a private pier that extends into the water, providing a perfect spot for fishing, sunbathing, or simply enjoying the gentle sea breeze. Whether you’re an early riser looking to catch the sunrise or a night owl reveling in the city lights reflecting on the water, this space is sure to become your favorite retreat. The four bedrooms are thoughtfully designed to ensure a restful night’s sleep with ample storage space. The three bathrooms are well-appointed and offer modern amenities, ensuring everyone has the space and convenience they need. Conveniently located near popular attractions and activities, this waterfront haven offers the best of both worlds – tranquility and accessibility. Immerse yourself in the coastal lifestyle and create lasting memories at our Large Waterfront Home with Views of the Ocean City Skyline. Book your stay now and let the waves be your lullaby while the city lights become your nightly spectacle!

Pool Access & 2 Mi to Beach! Ocean City Escape

West Ocean City, MD, US
3 Bedrooms 8 Guests
Sep 30 - Oct 7
$301 night

Gas Grill | 2 Mi to Boardwalk Amusements | 8 Mi to Assateague State Park Sun, sand, and coastal family fun — experience the best of the Atlantic at this Ocean City vacation rental! Located in Ocean Village, this condo features a balcony for morning coffee, a deck and grill for post-beach cookouts, and access to perks such as indoor and outdoor pools and a fishing pond! Cruise down to the boardwalk or head to Assateague Island to watch the wild horses. Book your ultimate Maryland getaway now! -- THE PROPERTY -- OCEAN VILLAGE COMMUNITY AMENITIES - Outdoor pool, indoor pool & hot tub - Tennis & basketball courts, fitness center - Playground - Fishing pond (catch & release) OUTDOOR LIVING - Deck, gas grill, outdoor dining - Balcony w/ 2 chairs & table INDOOR LIVING - Sunroom - Smart TVs, gas fireplace - Dining table - Washer, dryer - Central A/C & heating KITCHEN - Electric stove, oven, dishwasher - Drip coffee maker (starter coffee provided) - Toaster, microwave, blender - Cooking basics, spices, dishware & flatware ACCESSIBILITY - 2-story condo, stairs required - Bedrooms & full bathrooms on 2nd floor PARKING - Dedicated space (1 vehicle) - Community lot (1 vehicle) -- THE LOCATION -- - Nestled in the family-friendly Ocean Village community just minutes from coastal amusements - 1 mile to Baja Amusements - 2 miles to Trimper Rides of Ocean City, Jolly Roger at the Pier & Ripley's Believe It or Not! - 3 miles to Eagle’s Landing Golf Course - 4 miles to Ocean Downs Casino -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Quiet hours (12:00 AM-7:00 AM) SECURITY CAMERA INFORMATION - 2 exterior devices - Location: front & back doors - Coverage: facing outward Licence number: STR-6040

Bayshore Beach Bungalow 46

Ocean City, MD, US
1 Bedrooms 4 Guests
Aug 30 - Sep 1
$56 night

This cozy 1-bedroom, 1-bathroom vacation rental is perfectly situated a short walk from the beach and the vibrant boardwalk, providing the ideal blend of relaxation and entertainment. Surrounded by top dining options like Mother’s Cantina, Dry Dock 28, and Pit and Pub, gastronomic adventures await. It’s also conveniently near various putt-putt golf courses and the thrills of Jolly Rogers Amusement Park, ensuring your beach getaway is filled with joy and excitement. ✨ Canalfront Coastal Retreat – Walk to Beach, Boardwalk & Dining 🌊🚶‍♀️ Welcome to this charming canalfront getaway at 508 Robin Drive, Ocean City, MD! Perfect for couples or small families, this cozy 1-bedroom retreat offers peaceful water views, direct kayak access, and an unbeatable location just a short walk from the beach and boardwalk. Enjoy the best of Ocean City with dining, entertainment, and attractions right nearby. ⸻ 🛌 Where You’ll Sleep Bedroom 1: Queen bed — calm, cozy, and perfect for restful nights 😴 Living Area: Sleeper sofa & twin sleeper chair — great for additional guests 🛋️ Total Beds: 3 🛏️ Baths: 1 full bathroom 🛁 ⸻ 🏠 The Space This bright, coastal-inspired home is thoughtfully designed for comfort and relaxation. Living Area: Filled with natural light and peaceful canal views, featuring comfortable seating and a wall-mounted Smart TV — perfect for unwinding after a beach day 📺🌊 Kitchen & Dining: Well-arranged with modern appliances, ample counter space, and a cozy dining setup that makes preparing and enjoying meals easy 🍽️ Bedroom: A tranquil retreat with a queen bed, soft linens, ceiling fan, and tasteful coastal décor 🌙 Bathroom: Full bathroom with updated fixtures for a comfortable and refreshing stay 🚿 ⸻ 🚣 Waterfront Perks Canalfront location with direct access to the ramp 🌊 Easy launch access for kayaks — perfect for relaxing cruises along the water 🛶 ⸻ 🎢 Exclusive Guest Perk 🎟️ Discounted Jolly Roger Water Park Tickets! Planning a day at the water park? We offer a limited number of discounted Splash Mountain Water Park tickets for our guests on a first-come, first-served basis. Current discounted rates: Adults (Over 42") – $37 (regular price: $66) Children (Under 42") – $14 (regular price: $20) If you’re interested, please send us a message before purchasing your tickets. We’ll confirm availability and let you know if discounted tickets are still available for your stay. ⸻ 📍 Location, Location, Location Just a short walk 🚶‍♀️ or quick drive 🚗 to: 🏖️ Ocean City Beach — short walk away 🎡 Ocean City Boardwalk — easy walk for shops, arcades & nightlife 🌮 Mother’s Cantina — approx. 3-minute drive 🍽️ Dry Dock 28 — approx. 2-minute drive 🍔 Pit & Pub — approx. 3-minute drive ⛳ Mini golf courses — approx. 3–5 minute drive 🎢 Jolly Roger Amusement Park — approx. 5–7 minute drive ⸻ 🌟 Guest Favorites Canal views with kayak access 🛶 Walkable beach & boardwalk location 🏖️ Discounted water park tickets 🎟️ Cozy, bright interior with coastal charm ⭐ ⸻ 💡 Why Guests Love It Whether you’re starting your mornings with peaceful canal views, spending afternoons at the beach, or enjoying boardwalk nights and local dining, this Robin Drive retreat offers the perfect blend of relaxation, location, and fun — all in one cozy coastal space. ⸻ 🧺 STARTER KIT We provide essential linens and a starter supply kit to help you settle in. Please note that these items are not replenished during your stay. 🍽️ Kitchen Kit: - 1 roll of paper towels - 2 small trash bags - 2 large trash bags - Dish soap - 2 dishwasher pods - 1 sponge - 2 dish towels 🚿 Full Bathroom Kit: - 2 rolls of toilet paper per bathroom - Travel-size shampoo, conditioner, body wash, body lotion, and bar soap 🛏️ Linens & Towels: - Beds are made with sheets, pillowcases, shams, and a comforter - Sheets for sofa beds are provided and left in the room with the couch (not provided for trundles or rollaway beds) - Each guest receives 1 towel set (bath towel, hand towel, and washcloth) This property boasts a prime waterfront location, nestled alongside a serene canal. You and your guests will delight in direct access to the ramp, making it effortless to launch kayaks for a leisurely cruise along the water. Before check-in, guests are required to complete a pre-arrival verification. As part of this process, guests will be asked to choose either a refundable security deposit or a non-refundable damage protection plan option before check-in details are released. Oceans Edge Vacations does not accept or process Affirm payments. If financing options are displayed through VRBO or another booking platform, those programs are administered entirely by the third-party provider and are not supported by our reservation system. A valid government-issued photo ID is required to verify identity, confirm age, and finalize your booking. Access to the property will not be granted until verification is completed. A rental agreement must be signed prior to your stay. A valid credit card is required to be kept on file for incidentals, damages, or policy violations. Occupancy is limited to the number of guests listed on the reservation. Unauthorized guests or parties are strictly prohibited. Quiet hours are enforced from 10PM-9AM. Excessive noise or disturbances may result in fines or immediate removal from the property without refund. This property may be equipped with exterior security cameras for safety and verification purposes. There are no cameras inside the home. This home is equipped with noise monitoring devices that measure decibel levels only. These devices do not record conversations or audio. No smoking or vaping is permitted inside the home. Evidence of smoking will result in additional cleaning fees. No pets allowed unless explicitly approved. Unauthorized pets will result in additional charges. Guests are responsible for complying with all local laws, HOA rules, and community guidelines. Check-in and check-out times must be adhered to unless otherwise approved. Any violations of these policies may result in additional charges, cancellation of the reservation, or removal from the property without refund. Bedroom 1: Queen Bed Living room: 1 Sleeper sofa & 1 twin sleeper chair If you need to have a package delivered during your stay please note that our delivery pick up window is Monday-Friday 9am-5pm at our main office. Please reach out to obtain the address that the package would be delivered to. Please note Oceans Edge Vacations is not responsible for packages that are not shipped directly to our office. If you would like to inquire about requesting an early check-in, please note that all early check-in requests are based upon availability. Request are only reviewed 24 hours prior to your check-in date. There is an additional fee of $75 if we can accommodate this request for you. Our calendars do tend to full up rather quickly. If you see a spot open feel free to instantly book. This is a non-smoking unit. Oceans Edge Vacation Rentals charges a $1,000 fine for smoking in the unit. Due to the high volume of turnovers in season and to provide the latest check out possible, cleaners may be completing cleanings until 6PM. Trust & Safety: By booking a stay with us you give permission permission to the property manager to use a third-party to verify my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest verification can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions. Trailer Parking Not Allowed – Please note that boat trailers, RVs, and other large trailers are not permitted. The HOA have strict policies in place, and any trailers found on-site will be subject to immediate towing at the owner’s expense. We kindly ask all guests to make alternate arrangements for trailer storage prior to arrival. We warmly welcome you to our coastal haven and wish to ensure your stay is as enjoyable as possible. However, we kindly remind our guests that certain elements beyond our control, such as weather conditions, nearby construction activities, or the exuberance of neighboring celebrations, may influence your experience. Nestled close to nature’s bounty, our location invites occasional visits from local wildlife, including raccoons, foxes, diverse bird species including seagulls, and an array of insects. While these encounters are part of the natural charm of our setting, we diligently treat our properties to minimize unwanted guests and maintain your comfort. Should you encounter any aspect of nature that feels less than welcoming or experience any issues with appliances, HVAC systems, electrical components, or cleanliness, please do not hesitate to inform us promptly and provide photographic evidence. We require that you allow us the opportunity to rectify the problem during your stay, as our response time is typically less than an hour. We will make every effort to address and resolve the situation to the best of our ability. However, please understand that such natural occurrences or maintenance issues do not warrant refunds. By booking this property you agree and understand no refunds are given. Our commitment is to provide a serene and delightful escape, and we are here to assist in making your experience as pleasant as possible, within the harmony of our natural surroundings.

Pool, Beach Access! Canal-Front Ocean City Gem

Ocean City, MD, US
3 Bedrooms 8 Guests
Aug 30 - Sep 2
$444 night

Start planning your perfect coastal getaway at this 3-bed, 2-bath vacation rental in Ocean City! This newly updated condo offers all the essentials to make your beach days carefree, including a kitchen for prepping picnics and in-unit laundry to rinse the sand away. After exploring the amusements on the Ocean City Boardwalk, working on your tan at the community pool, and strolling along the shore, head home to bask in the ocean breeze from the balcony or unwind with a movie on the Smart TV. -- THE PROPERTY -- 26-0077375 | Walk to Beaches | Community Boardwalk | Canal Views | Private Gated Sunset Island Community Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin/Full Bunk Bed w/ Twin Trundle | Living Room: Queen Sleeper Sofa COMMUNITY AMENITIES (up to 6 guests included, on-site fee per addt'l guest): Outdoor pool, pool deck w/ seating, indoor pool, fitness center, walking trails, beach bar & restaurant, private beach CONDO FEATURES: Smart TVs, dining table, ceiling fans, soaker tub, vaulted ceilings, private balcony, outdoor seating KITCHEN: Dishwasher, refrigerator, stove/oven, microwave, drip coffee maker, toaster, cooking basics, dishware & flatware, trash bags & paper towels GENERAL: Free WiFi, complimentary toiletries, hair dryer, towels & linens, beach towels, washer & dryer, central heating & A/C, keyless entry FAQ: Quiet hours (12:00 AM-7:00 AM) ACCESSIBILITY: Single-story condo, stairs required to enter PARKING: Community garage (1 vehicle), community parking lot (1 vehicle) -- THE LOCATION -- SUN & SAND: Ocean City Beach (0.5 miles), Northside Park (4 miles), Maryland Beach (5 miles) FAMILY FUN: Splash Mountain Water Park (3 miles), Jolly Roger Amusement Park (3 miles), Ocean City Boardwalk (4 miles), mini golf, shopping, oceanfront dining, carnival rides, boat rentals MORE TO DO: Discoversea Shipwreck Museum (5 miles), Outlets Ocean City (6 miles), Ocean Pines Golf Club (10 miles) AIRPORTS: Salisbury Regional Airport (28 miles), Baltimore/Washington International Thurgood Marshall Airport (130 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story condo requires stairs to enter - NOTE: Up to 6 passes will be provided at no additional cost to access the community amenities. Any additional passes can be purchased on-site for $75 per person - NOTE: Please observe quiet hours from 12:00 AM to 7:00 AM - NOTE: Per Ocean City regulations, the maximum occupancy is limited to 4 unrelated guests Licence number: 0077375;0077375;0077375

Windjammer Beach House

Ocean City, MD, US
4 Bedrooms 10 Guests
Aug 29 - Sep 1
$302 night

Windjammer Beach House, a 4 bed, 3 bath marvel, boasts a stunning remodel with a lavish outdoor area and a shared tennis/pickleball court at its back door. The Runaway Bay 1 also has a community pool. Its prime location offers great walkability to the beach and top eateries like OC Wasabi, Restaurante Antipasti, and Barn 34, plus proximity to the boardwalk’s north end. This home blends modern comfort with leisure, making it a perfect retreat for those who appreciate luxury and accessibility. ✨ Windjammer Beach House – Pickleball Court, Pool Access & Coastal Comfort 🌊🎾 Welcome to Windjammer Beach House, a beautifully designed 4-bedroom, 3-bath coastal retreat in Ocean City that blends modern comfort with resort-style amenities. Thoughtfully laid out across multiple levels, this home is ideal for families and groups seeking space, convenience, and easy access to beachside fun. ⸻ 🛌 Where You’ll Sleep • Primary Suite (Second Floor): King bed, spa-like en-suite bath, private balcony 😴 • Bedroom 2 (Second Floor): Queen bed, spacious and serene 🛏️ • Bedroom 3 (First Floor): Queen bed with built-in bunk beds designed specifically for small children 🎉 • Bedroom 4 (First Floor): Two twin beds that can convert to a king for a $25 fee 🛌 • Total Beds: 6 • Baths: 3 full bathrooms 🛁 ⚠️ Important Note: This home accommodates up to 8 adults and 2 small children. The built-in bunk beds are designed for small/young children only and are not suitable for older children, teenagers, or adults. Please review the listing photos carefully to see the size and design of the built-in bunk beds before booking. ⸻ 🏠 The Space Main Living Area (First Floor): Step into a bright, open-concept living space where the kitchen and living room flow seamlessly together — perfect for gathering, entertaining, and relaxing after a day at the beach. The kitchen features state-of-the-art appliances, a large island, and ample seating, making it both stylish and functional. Please note that guests are not permitted to sleep on the living room couch. Kitchen: Fully equipped with modern appliances and generous prep space, ideal for home-cooked meals and group dining. Bedroom Layout: Two bedrooms are located on the first floor, offering easy access and flexibility, while the second floor hosts the primary suite and an additional bedroom for added privacy. ⸻ 🌳 Outdoor Living & Community Amenities • Private tennis & pickleball court just steps away 🎾 • Community pool located on the west end of the property 🏊 • Water access for fishing, crabbing, and kayaking 🌊 • Outdoor space ideal for relaxing and dining al fresco ⸻ 🏊 Pool Access Notice 📌 The community pool is managed by the HOA and not the host. Pool availability may be seasonal and is not guaranteed, as closures may occur due to maintenance, repairs, or end-of-season schedules. ⸻ 📍 Location, Location, Location This home offers excellent walkability and quick access to Ocean City’s top attractions. 🚶 Nearby & Walkable: • 🏖️ Ocean City Beach — easy access for sun, sand, and surf • 🎡 Mini-golf, restaurants, and family attractions nearby • 🍽️ Dining options for every taste just minutes away • 🎢 Jolly Roger Amusement Park — approx. 10-minute walk, rides and family fun • 🍝 Ripieno’s Italian Bistro — approx. 12-minute walk, cozy Italian dining 🚗 Short Drive: • 🍽️ Dry Dock 28 — approx. 3-minute drive, local favorite dining spot • 🛍️ 33rd Street Plaza — approx. 3-minute drive, shopping and essentials • 🎢 Ocean City Boardwalk — arcades, shops, dining, and classic seaside fun • 🛒 Grocery stores and everyday essentials close by ⸻ 🌟 Guest Favorites • Open-concept layout perfect for groups • Private pickleball/tennis court access • Community pool and water access • Primary suite with balcony and spa-like bath • Excellent location near beach and attractions ⸻ 💡 Why Guests Love It Windjammer Beach House delivers the perfect balance of relaxation and recreation. From pickleball matches and pool days to beach trips and boardwalk nights, this home offers space, comfort, and unbeatable coastal convenience for an unforgettable Ocean City stay. ⸻ 🧺 STARTER KIT We provide essential linens and a starter supply kit to help you settle in. Please note that these items are not replenished during your stay. 🍽️ Kitchen Kit: - 1 roll of paper towels - 2 small trash bags - 2 large trash bags - Dish soap - 2 dishwasher pods - 2 laundry pods - 1 sponge - 2 dish towels 🚿 Full Bathroom Kit: - 2 rolls of toilet paper per bathroom - Travel-size shampoo, conditioner, body wash, body lotion, and bar soap 🛏️ Linens & Towels: - Beds are made with sheets, pillowcases, shams, and a comforter - Each guest receives 1 towel set (bath towel, hand towel, and washcloth) - A washer and dryer are available for guest use should you wish to refresh towels or linens during your stay This is a townhome and can be accessed on ground level. There are 2 parking spots assigned to this property with street parking available. Before check-in, guests are required to complete a pre-arrival verification. As part of this process, guests will be asked to choose either a refundable security deposit or a non-refundable damage protection plan option before check-in details are released. Oceans Edge Vacations does not accept or process Affirm payments. If financing options are displayed through VRBO or another booking platform, those programs are administered entirely by the third-party provider and are not supported by our reservation system. A valid government-issued photo ID is required to verify identity, confirm age, and finalize your booking. Access to the property will not be granted until verification is completed. A rental agreement must be signed prior to your stay. A valid credit card is required to be kept on file for incidentals, damages, or policy violations. Occupancy is limited to the number of guests listed on the reservation. Unauthorized guests or parties are strictly prohibited. Quiet hours are enforced from 10PM-9AM. Excessive noise or disturbances may result in fines or immediate removal from the property without refund. This property may be equipped with exterior security cameras for safety and verification purposes. There are no cameras inside the home. This home is equipped with noise monitoring devices that measure decibel levels only. These devices do not record conversations or audio. No smoking or vaping is permitted inside the home. Evidence of smoking will result in additional cleaning fees. No pets allowed unless explicitly approved. Unauthorized pets will result in additional charges. Guests are responsible for complying with all local laws, HOA rules, and community guidelines. Check-in and check-out times must be adhered to unless otherwise approved. Any violations of these policies may result in additional charges, cancellation of the reservation, or removal from the property without refund. If you need to have a package delivered during your stay please note that our delivery pick up window is Monday-Friday 9am-5pm at our main office. Please reach out to obtain the address that the package would be delivered to. Please note Oceans Edge Vacations is not responsible for packages that are not shipped directly to our office. If you would like to inquire about requesting an early check-in, please note that all early check-in requests are based upon availability. Request are only reviewed 24 hours prior to your check-in date. There is an additional fee of $75 if we can accommodate this request for you. Please note that the Pool & Tennis courts are shared by Runaway Bay 1 guests. Our calendars do tend to full up rather quickly. If you see a spot open feel free to instantly book. We can hold dates if you contact us at Oceans Edge Vacations for a small fee. This is a non-smoking unit. Oceans Edge Vacation Rentals charges a $1,000 fine for smoking in the unit. Due to the high volume of turnovers in season and to provide the latest check out possible, cleaners may be completing cleanings until 6PM. Trust & Safety: By booking a stay with us you give permission permission to the property manager to use a third-party to verify my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest verification can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions. We warmly welcome you to our coastal haven and wish to ensure your stay is as enjoyable as possible. However, we kindly remind our guests that certain elements beyond our control, such as weather conditions, nearby construction activities, or the exuberance of neighboring celebrations, may influence your experience. Nestled close to nature’s bounty, our location invites occasional visits from local wildlife, including raccoons, foxes, diverse bird species including seagulls, and an array of insects. While these encounters are part of the natural charm of our setting, we diligently treat our properties to minimize unwanted guests and maintain your comfort. Should you encounter any aspect of nature that feels less than welcoming or experience any issues with appliances, HVAC systems, electrical components, or cleanliness, please do not hesitate to inform us promptly and provide photographic evidence. We require that you allow us the opportunity to rectify the problem during your stay, as our response time is typically less than an hour. We will make every effort to address and resolve the situation to the best of our ability. However, please understand that such natural occurrences or maintenance issues do not warrant refunds. By booking this property you agree and understand no refunds are given. Our commitment is to provide a serene and delightful escape, and we are here to assist in making your experience as pleasant as possible, within the harmony of our natural surroundings.

Wight Bay North 234

Ocean City, MD, US
2 Bedrooms 6 Guests
Aug 30 - Sep 1
$193 night

2026 updated floors ★★ Things to Know ★★ ✹ Must be 25+ to rent and stay - no graduating HS groups. ✹ One assigned parking space included ✹ Coin-operated laundry facility located on-site ✹ No cable TV. Smart TVs available for streaming ★★ Things to Love ★★ ✹ Private balcony offering canal and sunset views ✹ Outdoor pool, community boat slips, and elevator access ✹ Fully equipped kitchen and short walk to Seacrets, dining, and the beach Welcome to Wight Bay, a newly renovated 2-bedroom, 2-bath waterfront condo located on 47th Street — just a one-minute walk to Seacrets and a short stroll to the beach. Perfectly positioned in midtown Ocean City, this bayside retreat combines comfort, convenience, and incredible views. Step out onto the covered balcony to enjoy peaceful canal scenery and stunning sunsets, or head down to the outdoor pool and dock area for a relaxing afternoon on the bay. Inside, you’ll find a fully equipped kitchen, cozy furnishings, and everything you need for a memorable stay by the water. ★★ Sleeping Arrangements ★★ ✹ Primary Bedroom – Queen bed ✹ Bedroom 2 – Queen bed ✹ Living Area – Double sleeper sofa ★★ Frequently Asked Questions ★★ Do you provide linens and towels? ✹ Yes. All linens and bath towels are included, and every bed is made prior to arrival. ✹ For your stay, 6 bath towels, 3 hand towels and 3 wash cloths are provided. Is parking available? ✹ Yes. One assigned parking space is included with your stay. Does this property have a pool? ✹ Yes. Guests have access to the community’s seasonal outdoor pool. When are lifeguards on duty at the beach? ✹ Ocean City lifeguards are on duty from Memorial Day weekend through mid-September. Is there a coffee maker provided, and if so what kind? ✹ Yes. A standard drip coffee maker is provided. Please bring your own coffee and filters. Is an iron provided? ✹ Yes, this unit does include an iron and ironing board. Is there cable TV? Are there Smart TVs? ✹ No cable TV. Smart TVs available for streaming with your own accounts. Are pets allowed? ✹ No, pets are not permitted at this property. Is smoking allowed anywhere? ✹ No, smoking and vaping are not permitted inside the condo or on the balcony. What is the check-in and check-out time? ✹ Check-in begins at 4:00 PM and check-out is by 10:00 AM. ✹ Early check-in may be available between 1:00 PM and 3:00 PM for an additional priority cleaning fee. Please inquire after booking. ✹ Late Check-out may be available between 11:00 AM and 1:00 PM for an additional priority cleaning fee. Please inquire after booking. What is the minimum age to rent? ✹ Guests must be at least 25 years old to rent and must be present for the entire stay. Sorry, we do not rent to Senior Week or similar student groups. How do I access the property? ✹ Access is provided via keyless entry. You will receive your unique access code prior to arrival. What is included in the complimentary starter kit? ✹ Body soap, shampoo, toilet paper, paper towels, dish soap, laundry detergent, dishwasher pods, and a sponge. Attractions & Activities ✹ Beach Access – (0.2 miles) 5 minute walk ✹ Ocean City Boardwalk – (2.8 miles) 8 minute drive ✹ Assateague Island – (13 miles) 23 minute drive ✹ Jolly Roger Amusement Park – (1.4 miles) 5 minute drive ✹ Carousel Ice Rink – (3.6 miles) 8 minute drive ✹ Northside Park – (4.4miles) 11 minute drive ✹North bus stop - Coastal and 48th street (0.1 miles) 3 minute walk ✹South bus stop - Coastal Ave at 46th street (0.2 miles) 6 minute walk Steps From Your Door: ✹ Ocean City Visitor’s Center- (1.2 miles) 5 minute drive/ 15 minute walk ✹ Dough Roller Restaurant (0.2 miles) 2 minute drive/ 11 minute walk ✹ 7-11 convenience Store- (0.8 miles) 3 minute drive/ 16 minute walk ★★ Important Notices ★★ We’re delighted to welcome you to one of our vacation homes and want your stay to be as enjoyable as possible. Please keep in mind that beach life sometimes brings shifting weather, town celebrations, or nearby construction. You may also encounter local wildlife such as seagulls, raccoons, foxes, or the occasional bug. Our homes are treated regularly, but a touch of the outdoors is part of Ocean City’s natural charm. If something feels off — whether it’s an appliance not working correctly or an unexpected maintenance issue — please let us know right away. A quick photo helps, and our team typically responds promptly to resolve anything with as little disruption as possible. While these types of issues don’t qualify for refunds, we’ll always do our best to make your stay smooth. All rentals include our full linen and towel package. Every bed will be made before you arrive, and each guest receives one bath towel along with fresh sheets and pillowcases. After booking you will be asked to complete a check-in form. This form includes providing your name, contact information, birthday, government photo ID, and signing rental lease agreement. This is to ensure age, identity, and protection of our home. Please respect the home as if it were your own. An additional $500 excessive cleaning fee may apply if the property is left in unacceptable condition, such as requiring cleanup of vomit or urine. Ocean City has a noise control ordinance that makes it unlawful to cause or permit noise levels which exceed those set by the Department of the Environment (COMAR 26.02.03.02) or violate Chapter 30, Article V of the Town Code. Violations are grounds for eviction under Maryland law. ❗ Each property has its own set of house rules. Please review these carefully before booking, as completing your reservation confirms your agreement to follow them. Failure to comply may result in fines or removal without refund. ❗

The Chateau 304

Ocean City, MD, US
2 Bedrooms 6 Guests
Aug 30 - Sep 2
$295 night

Enjoy laid back coastal living at this comfortable 2 bedroom, 2 bathroom condo in The Chateau on Mooring Road in Ocean City, MD. Perfectly positioned along the canal with beautiful bay sunset views, this Ocean City vacation rental offers a peaceful setting while still keeping you close to the beach, dining, and everything midtown Ocean City has to offer. Whether you are spending the day on the water or relaxing on the balcony as the sun sets over the bay, this condo makes it easy to settle into vacation mode. Inside, the condo features an upgraded galley kitchen with modern finishes and everything needed for preparing meals after a day at the beach. The open living and dining space creates a comfortable place to gather, while the private balcony overlooking the canal gives guests the perfect spot for morning coffee or evening sunsets. With two full bathrooms, comfortable sleeping arrangements, and the convenience of Wi-Fi, central air, and easy parking, the condo is well suited for couples, families, or small groups looking for a relaxing stay in Ocean City MD. Located in a quiet canalfront area, guests can enjoy easy access to the beach, local restaurants, mini golf, nightlife, and shopping throughout midtown Ocean City. Spend the afternoon exploring the boardwalk, enjoy fresh seafood nearby, or head out for boating, fishing, and water activities right around the bay. The location also makes it easy to visit North Ocean City, Fenwick Island, and Assateague Island during your stay.

Vacation Rentals in Ocean Pines by Amenities & Features

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Vacation Rentals Near Ocean Pines

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