Pet-friendly vacation rentals in Chestertown, MD

Sep 14 - 17

$986 night

This short-term rental has an occupancy of 10 individuals with a max. of 8 guests being 18 years or older. Working Farm on Reeds Creek This lovely working farm is on a peninsula situated between Grove Creek and (surely not to your surprise) Reed Creek, which is just off of the Chester River. On this peninsula, historically called Wright’s Neck, sits the Reeds Creek house, built by Colonel Thomas Wright in 1775. The Creek Cottage, a second home on the property, is a modern addition to the 170-acre farm offering privacy in the presence of a historical setting and powered by solar energy. Enjoy the private surroundings of the farm from the cottage’s private pool or take a stroll or a leisurely bike ride to the sandy beach on Reed Creek. Get a sense of history by booking your stay at The Creek Cottage on Reed Creek Farm today. PROPERTY FEATURES: Acreage: 170 acre farm. Waterfront: Reed Creek Dock: 100ft dock with 3ft MLW, water and electricity. Water Toys: 2 single kayaks, 2 canoes and 2 paddle boards are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option. Fireplaces: Wood-burning. Firewood is not provided. Fire Pit: Propane is provided. Grill: Propane grill. Propane is provided. Pet Policy: This property is dog friendly for up to two medium size dogs 60lbs and under. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

Gorgeous Creek Side Ranch-Style Estate With Dock

Queenstown, MD, US

4 Bedrooms • 11 Guests

Aug 25 - 27

$277 night

Welcome to our Chesapeake Oasis! Quiet Queenstown is a beautiful and historic part of Maryland’s Eastern Shore bordering the Chesapeake Bay. We welcome you to enjoy a home away from home at our 4-bedroom ranch-style house. Off the beaten path and perfect for multi-generation families, you’ll enjoy the privacy of being off the main road but within a short drive to all that the Eastern Shore has to offer. Relax, unwind, and enjoy! This is a 1-story, 4-bedroom, 2.5-bath property with a beautiful, communal kitchen overlooking the back yard and the cove. The fully-appointed kitchen includes a large island with a breakfast table for groups who like to socialize around good food. We also have a formal dining room and a wine bar with temperature-controlled cooler. The en suite primary bedroom features a king bed, window seats overlooking the cove, and a large internet-enabled smart TV. The three other bedrooms feature one king bed, one queen bed, and one bunk bed (twin XL on top and queen on the bottom bunk). All four bedrooms have internet-enabled smart TVs with wi-fi apps for you to log in to your favorite streaming services. An additional office space features a pull-out with full size mattress, and a 65” smart TV, perfect for movie nights! Bring your friends and family to enjoy your stay with the variety of bedroom options available. Guests have access to the entire home, including the wide-open front yard and fenced-in back yard, the dock, and the laundry. (The garage is currently reserved for storage.) Guest internet is included with your stay; fiberoptic service to the house provides terrific wi-fi speeds for your devices in the +500 Mbps up/down range. With Sadler’s Cove in our back yard, you’ll have easy access to the water if you choose to bring your own canoe or kayak. The bucolic views of the neighboring farm and the serenity of Sadler’s Cove lend themselves to a slower pace and peaceful moments on the back deck or around the firepit with your favorite beverage or glass of wine. The conserved forest on the opposite shore is home to blue herons, hawks, bald eagles, terrapins, and a multitude of other wildlife. We recommend a rental or personal car being used to navigate around Queenstown and to/from our home. There is ample parking provided at the house and no easy access to public transportation in the area. To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -4 & 5+ bedroom units: $50 per guest, per night after 8 or 10 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $150 -1–2 hours: $300 -2–3 hours: $450 -3+ hours: $600 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel’s cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Bay Breeze

Grasonville, MD, US

Aug 24 - 27

$1,240 night

The Perfect Escape! This exceptional 5-bedroom, 3-bathroom shore house sits on a 1+ acre waterfront lot and boasts endless nautical activities, including kayaking, a private pier, and a large pool overlooking the Chesapeake Bay. Offering a welcoming interior and providing large entertainment spaces, an expansive great room, first-floor master bedroom suite, and sunroom. Drift off to sleep each night in the oversized main suite that comes complete with an ensuite bathroom and picture-perfect water views. Enjoy the indoor/outdoor lifestyle in the beautifully maintained backyard which includes a brand-new stone patio, large in-ground heated pool (Heat is available for an additional fee), gas firepit, and large grassy areas for yard games with spectacular views. An ideal destination for any vacation. With an exceptional location in a desirable section of Queen Anne’s County. Please Note: This house is in a quiet residential neighborhood, so is not compatible with any loud parties, and it is imperative that if you bring a pet that the pet not be allowed off property without a leash. The westerly view over the water provides exceptional sunsets - enjoy a nightly sunset cocktail and experience the waterfront lifestyle you’ve been looking for. Book this one quickly or miss out. PROPERTY FEATURES: Waterfront: Chesapeake Bay Dock: 50ft private dock. No water or electricity is available. Guests are permitted to tie a boat to the dock. Water Toys: 1 kayak is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 20 x 40 private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option. Grill: Propane grill. Propane is provided. Pool Shed: Pool toys, loungers, tables, pool toys, a beverage fridge and yard games. Pet Friendly: Owner will consider pets, call reservations at 443.664.4039 to inquire. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Sleep Sofa - Double - 1 / Sleep Sofa - Double - 1 / Queen - 1 / Queen - 1 / Bunk Bed - Single over Single - 2 / Single Bed - Twin Sized - 2 /

Waterfront Annapolis Cottage: Fire Pit & Pier

3 Bedrooms • 5 Guests

Aug 26 - 28

$242 night

Located on Meridith Creek, this charming vacation rental features a large yard, fishing pier, and an outdoor space with dining, furniture, and a fire pit. Inside this 3-bed, 1-bath cottage, cozy furniture decorates the open living area. During your stay at this lovely cottage, stroll through the quaint Annapolis Historic District, visit the US Naval Academy, or take a day trip to D.C. and Baltimore. It is the perfect home base for your next Maryland getaway on the water! -- THE PROPERTY -- STR Permit #142832 | Meredith Creek Access | Crab Traps Provided | Covered Outdoor Dining | Dock Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Twin Bunk Bed Note: The top bunk is intended for children's use only. OUTDOOR LIVING: Patio, covered dining table, fire pit, patio furniture w/ cushions, yard, double BBQ pit, swimming dock, fishing pier, Meredith Creek access, on-site crabbing (traps provided) INDOOR LIVING: Open layout, stone accent wall, couch & reclining chairs, flat-screen satellite TV, dining table KITCHEN: Fully equipped, refrigerator, stove/oven, dishwasher, microwave, 1-cup coffee maker, teapot, cooking basics GENERAL: Free WiFi, linens & towels, laundry machines, central air conditioning, ceiling fans, closets, landline FAQ: Pet fee (paid pre-trip) PARKING: Driveway (2 vehicles) -- THE LOCATION -- HISTORIC DOWNTOWN: William Paca House & Garden (7.9 miles), Armel-Leftwich Visitor Center (8.0 miles), Annapolis City Dock (8.1 miles), Maryland State House (8.1 miles), Annapolis Maritime Museum (9.3 miles) OUTDOOR ACTIVITY: Meredith Creek (on-site), Sandy Point State Park (2.3 miles), Annapolis City Marina (8.8 miles), Quiet Waters Park (14.2 miles), Port Annapolis Marina (15.0 miles), Herrington Harbour - Herrington on the Bay (26.0 miles) ATTRACTIONS: Crypt of John Paul Jones (7.2 miles), Hammond-Hardwood House (7.3 miles), The Chesapeake Children’s Museum (9.8 miles), Pirate Adventures on the Chesapeake (10.0 miles), Top of the World Observation Level (35.4 miles), Fort McHenry National Monument & Historic Shrine (36.7 miles) US NAVAL ACADEMY: Navy-Marine Corps Memorial Stadium (7.3 miles), Alumni Hall (7.5 miles), US Naval Academy Museum (7.6 miles), Naval Academy Chapel (7.7 miles), Drydock Restaurant (8.2 miles), Memorial Hall (8.2 miles) DAY TRIPS: Baltimore, MD (31.7 miles), Washington D.C. (36.7 miles), Rehoboth Beach, DE (85.8 miles), Philadelphia, PA (117 miles) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (23.9 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 - Pet friendly with $50 fee (+ fees & taxes, 1 dog max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in -Note: The top bunk is intended for children's use only. Licence number: STR-142832

River Cottage

Severna Park, MD, US

1 Bedrooms • 2 Guests

Aug 31 - Sep 2

$305 night

Experience the Difference: Professionally Managed by iTrip Annapolis This adorable cottage sits on 3 picturesque acres overlooking the Magothy River. The charming, newly-furnished River Cottage is perfect for an escape for two! There is a full kitchen with complimentary coffee and a waterfront back patio - the perfect place to enjoy enjoy a glass of wine. Head further outside to the waterfront pier and fire pit overlooking the Magothy River. The Cottage shares the property with the main house, River Breeze, which is also available for rent. The River Cottage is wonderful for a couple coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops just a short drive to downtown Annapolis, or stay put and enjoy the lush, expansive property and spoil yourself with the million dollar views from your very own private patio! SLEEPING ARRANGEMENTS 1 BR / 1 BA / Sleeps 2 adults: Bedroom -Queen bed -Flatscreen TV -Full hall bath with stand-up shower HIGHLIGHTS: -Private waterfront pier -Full kitchen -Water access from private pier on the Magothy River -Game room with pool table, bar stools and TV, shared with main house. -Charcoal Grill -Shared firepit with the main house with seating for 6 -Eat-in kitchen seats 4 -High Speed Internet and WiFi -Big Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking in the driveway -Dogs allowed if $150 pet fee per pet is paid prior to check-in. Property Distance to: -Downtown Annapolis – 11 miles -U.S. Naval Academy – 11 miles -Washington, DC – 35 miles -Baltimore - 19 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. License: STR00484

River Breeze

Severna Park, MD, US

4 Bedrooms • 13 Guests

Sep 30 - Oct 2

$1,236 night

Experience the Difference: Professionally Managed by iTrip Annapolis *Ask us about renting the 1Bedroom/1Bath River Cottage on the same property. This stunning historic home, located on 3 picturesque acres overlooking the Magothy River, has been renovated and professionally-decorated from top to bottom. The open space has a massive eating, living and family room space, suitable for a multi-family visit. Separating the cozy conversation/gaming swivel-chair space from the oversized family room space is a custom bar height dining table with seating for up to 12, designed specifically to fit this special space. Head out to the waterfront screened-in patio and enjoy a glass of (complimentary!) wine. Head further outside to the new circle of artfully-crafted chairs around the firepit overlooking the private pier and beach. The home is ideal for families looking for all of the living and sleeping space on one floor. The house has 4 bedrooms and 3 full baths. The bedrooms are divided into 2 wings - a family wing and a guest wing. The Family wing has the spacious master suite features a private newly-renovated bath with combo bathtub/shower and private entrance to a cozy enclosed temperature-controlled sleeping porch off the Master suite with twin daybeds, perfect for sipping coffee or wine and enjoying the view, or alternatively can be utilized as twin beds! The 2nd guest room on the same wing has sleeping for 5 in the Queen bedroom, twin with trundle and pullout twin futon with private bath with shower in the hall. The Guest wing is a waterfront Queen bedroom with its own door out to the back patio and a shared full bath in the hall. The second guest room on the wing has a platform King bed with plenty of closet space. The beautifully-decorated spacious eat-in kitchen has been supplied with everything guests need for their stay. There is also a full laundry room/mudroom. Head out to visit your neighbors at the sweet 1-bedroom cottage next-door or inquire about renting that as an additional space (which may be rented by a 3rd party during your stay). The home has plenty of parking and space to explore with the pups and little family members. The home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. SLEEPING ARRANGEMENTS 4 BR / 3 BA / Sleeps 8 adults and 4-8 kids/teens: Family Wing: Grand Master Suite: -King bed -Private temperature-controlled sleeping porch with 2 Twin beds -Private bathroom with combo bathtub/stand-up shower -Flatscreen TV Guest Bedroom across the hall from Master Suite: -Queen bed -Twin with Twin Trundle -Twin futon -Full Hall Bath with stand-up shower Guest Wing: Queen Waterfront Guest Bedroom: -Queen bed -Private entrance to waterfront porch -Full hall bath with stand-up shower King Bedroom: -King Bed -Full hall bath with stand-up shower HIGHLIGHTS: -Private waterfront pier -Massive waterfront covered screened-in patio with a dining table and plenty of seating -BBQ Gas grill (propane tank provided) -Extra large gathering space with living, dining and family room areas -Gourmet kitchen -Water access from private pier on the Magothy River -Paddle board (located in the boat house) -Covered temperature-controlled sleeping porch -Game room with pool table, bar stools and TV. -Firepit with seating for 6 -Dining room table seats 12 -Eat-in kitchen seats 6 -High Speed Internet and WiFi -Big Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full Laundry room with Washer & dryer located inside the home -No smoking -Dogs allowed if $150 pet fee is paid prior to check-in. Property Distance to: -Downtown Annapolis – 11 miles -U.S. Naval Academy – 11 miles -Washington, DC – 35 miles -Baltimore - 19 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. License: STR00484

River Breeze Estate - Commissioning Week Only

Severna Park, MD, US

5 Bedrooms • 15 Guests

Sep 30 - Oct 2

$989 night

Experience the Difference: Professionally Managed by iTrip Annapolis Spread out for Commissioning Week on this historic 3-acre property on the Severn River! There is both a beautiful spacious 4 Bedroom home AND a separate cottage with a 1 bedroom and 1 bath. This stunning historic home, located on 3 picturesque acres overlooking the Magothy River, has just been renovated and professionally-decorated from top to bottom. The open space has a massive eating, living and family room space, suitable for a multi-family visit. Separating the cozy conversation/gaming swivel-chair space from the oversized family room space is a custom bar height dining table with seating for up to 12, designed specifically to fit this special space. Head out to the waterfront screened-in patio and enjoy a glass of (complimentary!) wine. Head further outside to the new circle of artfully-crafted chairs around the firepit overlooking the private pier and beach. The home is ideal for families looking for all of the living and sleeping space on one floor. The house has 4 bedrooms and 3 full baths in the main house. The bedrooms are divided into 2 wings - a family wing and a guest wing. The Family wing has the spacious master suite features a private newly-renovated bath with combo bathtub/shower and private entrance to a cozy enclosed temperature-controlled sleeping porch off the Master suite with twin daybeds, perfect for sipping coffee or wine and enjoying the view, or alternatively can be utilized as twin beds! The 2nd guest room on the same wing has sleeping for 5 in the Queen bedroom, twin with trundle and pullout twin futon with private bath with shower in the hall. The Guest wing is a waterfront Queen bedroom with its own door out to the back patio and a shared full bath in the hall. The second guest room on the wing has a platform King bed with plenty of closet space. The beautifully-decorated spacious eat-in kitchen has been supplied with everything guests need for their stay. There is also a full laundry room/mudroom. The sweet 1-bedroom cottage next-door is perfect for the additional family members needing some of their own space. The home has plenty of parking and space to explore with the pups and little family members. Enjoy the many restaurants, historical attractions, and shops just a short drive from downtown Annapolis, or spoil yourself with the million dollar views from the screened-in patio! **COVID - 19 Extra Special Precautions: Our guests’ and staff’s health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure they meet CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). Main House SLEEPING ARRANGEMENTS: 4 BR / 3 BA / Sleeps 8 adults and 4-8 kids/teens: Family Wing: Grand Master Suite: -King bed -Private temperature-controlled sleeping porch with 2 Twin beds -Private bathroom with combo bathtub/stand-up shower -Flatscreen TV Guest Bedroom across the hall from Master Suite: -Queen bed -Twin with Twin Trundle -Twin futon -Full Hall Bath with stand-up shower Guest Wing: Queen Waterfront Guest Bedroom: -Queen bed -Private entrance to waterfront porch -Full hall bath with stand-up shower King Bedroom: -King Bed -Full hall bath with stand-up shower Cottage - SLEEPING ARRANGEMENTS 1 BR / 1 BA / Sleeps 2 adults: Bedroom -Queen bed -Flatscreen TV -Full hall bath with stand-up shower -Full kitchen Eat-in kitchen seats 4 HIGHLIGHTS: -Private waterfront pier -Massive waterfront covered screened-in patio with a dining table and plenty of seating -BBQ Gas grill (propane tank provided) -Extra large gathering space with living, dining and family room areas -Gourmet kitchen -Water access from private pier on the Magothy River -Covered temperature-controlled sleeping porch -Game room with pool table, bar stools and TV. -Firepit with seating for 6 -Dining room table seats 12 -Eat-in kitchen seats 6 -High Speed Internet and WiFi -Big Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full Laundry room with Washer & dryer located inside the home -Non-Smoking -Dogs allowed if $150 pet fee per pet is paid prior to check-in. Property Distance to: -Downtown Annapolis – 11 miles -U.S. Naval Academy – 11 miles -Washington, DC – 35 miles -Baltimore - 19 miles *************** * Welcome Gift Basket * Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. License: STR00484

Coastal Modern Retreat | Large Group Getaway on 2 Acres

Arnold, MD, US

6 Bedrooms • 15 Guests

Aug 30 - Sep 1

$201 night

Welcome to Coastal Modern Retreat, your ideal family and group getaway in beautiful Arnold, MD! This spacious 6 bed, 4 bath home offers two kitchens, two living spaces, a deck with BBQ, and room to gather or unwind. Set on 1.8 peaceful acres, enjoy amazing sunsets and a short drive to the beaches, restaurants, and nightlife. With a king suite, bunk room, and sleeper sofa, there’s space for everyone to relax and make memories. ✨ Coastal Modern Retreat – Spacious, Pet-Friendly Escape with Dual Living Areas 🐾🌊 Welcome to Coastal Modern Retreat, a beautifully designed home located in Arnold, Maryland—perfect for families and groups looking for space, comfort, and a peaceful setting close to the water. Set on 1.8 serene acres, this retreat offers multiple living areas, two kitchens, and plenty of room to gather or unwind while enjoying coastal sunsets and easy access to nearby beaches, dining, and nightlife. ⸻ 🛌 Where You’ll Sleep Primary Suite: King bed — spacious and relaxing 😴 Bedroom 2: Queen bed — comfortable and inviting 🛏️ Bedroom 3: Queen bed — cozy and bright 🛏️ Bedroom 4: Queen bed — great for guests or family 🛏️ Bedroom 5: Full bunk bed — perfect for kids 🎉 Bedroom 6: Twin bed — built-in and kid-friendly 🛌 Living Room: Full sofa bed — additional sleeping space 🛋️ Total Beds: 7 🛌 Baths: 4 full bathrooms 🛁 ⸻ 🏠 The Space This spacious home is thoughtfully laid out to give everyone room to spread out while still enjoying time together. Living Areas: Two separate living spaces — ideal for group gatherings, movie nights, or quiet relaxation. Kitchens: Two fully equipped kitchens make it easy to prepare meals for large groups or multiple families. Only one microwave available in upstairs Kitchen. 🍽️ ⸻ 🐾 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. ⸻ 🌿 Outdoor Space Large deck with BBQ grill — perfect for outdoor meals and evening hangouts 🍔 Expansive 1.8-acre lot offering privacy, peaceful surroundings, and beautiful sunset views 🌅 ⸻ 🚗 Parking Ample on-site parking available for multiple vehicles 🚘 ⸻ 📍 Nearby Attractions 🚗 Short Drive: 🛒 Safeway — approx. 3-minute drive, groceries and essentials 🍜 Hong Kong Restaurant — approx. 4-minute drive, Chinese cuisine 🍝 Bella Italia — approx. 4-minute drive, Italian favorites 🥯 Naval Bagels — approx. 4-minute drive, local breakfast favorite 🌊 Jonas Green Park Beach — approx. 8-minute drive, bay views, picnic areas, and waterfront walks 🏖️ Sandy Point State Park — approx. 12-minute drive, sandy beaches, swimming, and Chesapeake Bay views ⸻ 🌟 Guest Favorites Pet-friendly accommodations 🐾 Two kitchens and two living areas — ideal for large groups 🏠 Spacious layout with room for everyone 🛌 Private setting with sunset views 🌅 Close to beaches, parks, and waterfront attractions 🌊 ⸻ 🧰 Extras & Amenities High-speed Wi-Fi 📶 Two fully equipped kitchens 🍳 Washer & dryer 🧼 Starter supply kit included 🧴 ⸻ 💡 Why Guests Love It Guests love the combination of space, privacy, and flexibility this home offers. With multiple living areas, sleeping options for all ages, a pet-friendly setup, and quick access to Chesapeake Bay beaches, parks, and Annapolis-area dining, Coastal Modern Retreat is the perfect place to relax, reconnect, and make lasting memories. ⸻ 🧺 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. We do not provide linens for sofa beds. 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.

Whitehall Acres

Easton, MD, US

Aug 31 - Sep 3

$1,568 night

Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a separate dining room, flow-through living area and a generous bonus suite. The appliances enhance this gorgeous recently remodeled kitchen, equipped with quartz countertops and sprawling island. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, private balcony, and water views. The wonderfully secluded backyard boasts a patio dining space and a 18’x39’ built-in swimming pool with tanning ledge. You will love this waterfront vacation home! Well placed in a sought-after Talbot County neighborhood. This unique home will book fast! Talbot County STR License STRN-22-36 PROPERTY FEATURES: Waterfront: Leeds Creek Dock: Private dock with bench and beautiful views. Guests are not permitted to tie a boat to the dock. Water Toys: 2 kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Brand new 18’x39’ built-in swimming pool with tanning ledge. Guests swim in pool at their own risk. Pickleball Court: Pickleball court for guest use. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Available for guest use. BED SIZES: King - 1 / King - 1 / Queen - 1 / Queen - 2 / Bunk Bed - Single over Single - 1 / Sleep Sofa - Queen - 1 /

Phillip Clayton House

Aug 31 - Sep 2

$797 night

Experience the Difference: Professionally Managed by iTrip Annapolis Historic Philip Clayton House – Downtown Annapolis Retreat Step into Annapolis history at the Philip Clayton House, a landmark residence built in 1834. Located just one block from the City Dock, 3 blocks from the U.S. Naval Academy and the lively shops and restaurants of Downtown Annapolis, this home blends historic character with modern comforts for an unforgettable stay. With nearly 200 years of stories behind its walls, the home has been thoughtfully renovated to balance original charm with modern livability. A bright family room opens to a private patio and fenced backyard—perfect for morning coffee, al fresco dining, or evenings around the fire pit. There are 4 spacious bedrooms and 2.5 bathrooms, comfortably accommodating up to 10 guests. The gourmet kitchen serves as the heart of the home, featuring a large central island, top-quality appliances, and plenty of space for family meals or entertaining. Sleeping Arrangements (Sleeps 10): King Suite (2nd Floor): King bed with ensuite full bath Garden Bedroom (2nd Floor): Queen bed Americana Bedroom (2nd Floor): Queen bed 3rd Floor Bedroom: Two King beds Additional Baths: Full hall bath on 2nd floor + half bath on main level Highlights: Private backyard with dining for 6, Adirondack chairs, and fire pit Propane BBQ grill Multiple dining areas in the kitchen, dining and family rooms (total seating for 16) Smart TVs, WiFi, and luxury linens Keyless entry and in-home laundry Dog-friendly ($150 per pet fee to be charged prior to checkin) Parking: Convenient loading zone on street in front of house with parking around the block in the easy to access Hilman garage. Daily rate $23.25. Guests must be 25+ or accompanied by an adult No smoking, parties, or events permitted Steep staircases may not suit those with mobility issues Nearby Attractions: U.S. Naval Academy: 3 blocks City Dock & Downtown Annapolis: Walking distance Washington, D.C.: 30 miles Baltimore: 25 miles Your stay begins worry-free with a starter kit of coffee, toiletries, and household essentials. Freshly laundered linens await on every bed so you can settle in and enjoy the best of Annapolis—history, charm, and convenience all in one. License: 002292_2025

Liberty Call

Arnold, MD, US

4 Bedrooms • 9 Guests

Aug 26 - 28

$447 night

Experience the Difference: Professionally Managed by iTrip Annapolis Located less than 15 minutes from Downtown Annapolis, this newly-renovated spacious home awaits you. Enjoy the large screened-in patio overlooking the spacious fenced-in yard or, head inside to relax in the 4 bedrooms, 2.5 baths with a fully-finished recreation room on the lower level. Families will love that there are multiple hangout spaces throughout the home. Spread out in the main floor great room with the gourmet kitchen overlooking the large flatscreen TV in the living room. The USNA graduate owner has refinished the kitchen with the gourmet chef in mind! Enjoy entertaining your guests while they sit around the kitchen island with seating for 6. Curate a large family meal and spend time around the dining room table with seating for 6 more. Walk out onto the furnished screened-in porch overlooking the quiet private fenced-in backyard. Head upstairs to the 4 bedrooms and 2 full baths. The King suite with an en-suite bath has a deluxe luxury shower. The Family guest room has a Queen bed and futon that folds out to a full bed. The 2nd Queen bedroom features a dedicated work space with a desk and chair in a sunny private alcove. The 4th bedroom features a full bed. The 3 guest rooms upstairs share the hall full bath with a shower/tub combo. The lower-level features both a full recreation room as well as a private workout room with an exercise bike and weights. Watch football on the sectional sofa around the large TV or challenge each other to a game of air hockey or foosball. The home is located in a quiet neighborhood in Arnold, just minutes from Downtown Annapolis, with easy access to the Naval Academy, the Bay Bridge, and highways to Baltimore and Washington D.C Inquire about discounted extended stays! SLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 9 adults or 8 adults + 2 kids: 2nd Floor King Suite: -King Bed -Private en suite bathroom with custom shower Queen Family Guest Room -Queen Bed -Futon that pulls out to a Full bed (could sleep 2 kids) -Full bath in the hall with shower/bath combo Queen Guest Room with desk -Queen Bed -Dedicated work space -Full bath in the hall with shower/bath combo Full Guest Room -Full Bed -Full bath in the hall with shower/bath combo HIGHLIGHTS: -Spacious open plan kitchen, dining room and living room -Dining room table seats 6 -Additional seating at kitchen bar for 6 -Spacious furnished screened in porch with dining table and sofa -Multiple living room spaces -Community park -Private fenced-in backyard -High Speed Internet and WiFi -2 Big Screen TVs -2 coffee makers: Keurig and Drip Coffee maker with starter packs of coffee/creamers -Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for 2 cars in driveway/street parking available -Full-sized washer & dryer in lower level recreation room -Non-Smoking -Dogs allowed with $150 non-refundable per pet fee paid prior to checkin. -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: -Downtown Annapolis – 7 miles (12 mins) -U.S. Naval Academy – 7 miles (12 mins) -Washington, DC – 33 miles -Baltimore - 22 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels in the baths. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents. Please respect the neighbors and neighborhood. No parties. Quiet neighborhood hours are 10pm-8am! Check-in time: 4:00 pm Check-out time: 11:00 am License: STR00548

Private Boat Dock! Wye River Retreat in Queenstown

Queenstown, MD, US

Aug 25 - 28

$1,446 night

Expansive Outdoor Relaxation Space | Sunroom w/ Views | Pet Friendly w/ Fee Dive into waterfront fun when you stay at this spacious vacation rental in Queenstown. The house offers 5 bedrooms, 3 full baths, and 2 half baths to accommodate your whole crew. Sip your morning coffee on the screened patio as you plan your day's activities, then kayak on the river or venture out to St. Michaels to sample the fresh seafood. Afterward, return home for a cookout with loved ones. Book today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS -Bedroom Suite 1 (Main Level): 1 king bed w/ en-suite full bathroom (standing shower) -Bedroom 2 (Main Level): 1 queen bed w/ hall access to full bathroom (shower/tub combo) -Bedroom 3 (Sub-Level): 2 twin beds w/ hall access to full bathroom (standing shower) -Bedroom 4 (Sub-Level): 1 king bed w/ hall access to full bathroom (standing shower) -Bedroom 5 (Sub-Level): 1 queen bed w/ hall access to full bathroom (standing shower) INDOOR LIVING - 5 Smart TVs w/ cable - 2 fireplaces - Dining table - Board games, PlayStation OUTDOOR LIVING - Dock, 2 kayaks, life vests (various sizes) - Pool (not heated, seasonal from May to October) - Wood-burning fire pit - Gas grill - Yard, swing set - Screened patio KITCHEN - Stove/oven, refrigerator, dishwasher - Dishware/flatware, cooking basics - Drip & Keurig coffee makers - Microwave, blender, toaster, toaster oven - Trash bags & paper towels GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Washer/dryer - Linens/towels & hair dryer FAQ - Pet fee (paid pre-trip) - Not childproofed ACCESSIBILITY - Multi-level home, steps to enter - All bedrooms & full baths on upper & lower levels PARKING - Driveway (6 vehicles) - Garage (2 vehicles) -- THE LOCATION -- - Wye East River on-site - Close to outlets - 8 miles to Main Street - 28 miles to the United States Naval Academy - 34 miles to St. Michaels - 44 miles to Baltimore/Washington Int'l 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, 2 max) - 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 steps to enter. While it offers a half bath on the main level, interior stairs are required to access all bedrooms and full baths on the upper and lower levels - The property may not be suitable for children due to the unfenced pool and waterfront nature of the property - The pool is available seasonally from May to October

Leeds Landing

Easton, MD, US

Aug 30 - Sep 2

$1,334 night

Nestled on the serene waterfront of Leeds Landing, this expansive single-story retreat is the perfect haven for families and friends. Boasting a prime location, this home sits on a tranquil 2+ acre lot on Leeds Creek, offering stunning views and direct access to the Miles River. The deep water dock (MLW 4’) makes it easy to enjoy fishing, crabbing, or boating adventures. Inside, the spacious living area is designed with comfort in mind, featuring five cozy bedrooms and three full bathrooms, comfortably accommodating up to ten guests. The master suite offers a luxurious king bed, while additional bedrooms include a queen bed, a crib, two bunk beds, and a twin bed, ensuring everyone has a restful place to sleep. The sunroom and screened porch provide breathtaking views of the backyard pool and waterside fire pit, perfect for relaxing or enjoying evening meals. The fully equipped kitchen has everything you need to prepare a meal, and the dining area seats all guests comfortably. The outdoor dining area, complete with a gas grill and outdoor seating, is ideal for barbecues and al fresco dining. For those who enjoy water activities, a canoe is provided, and a private pool is available for a refreshing dip. Just a short distance away, explore the charming town of Easton, MD, where you can visit the Easton Historic District, enjoy dining at local favorites like The Easton Crabhouse, or take a stroll along the scenic Miles River. Whether you’re seeking adventure or relaxation, this waterfront retreat promises an unforgettable getaway. Book your stay today and experience the perfect blend of comfort, convenience, and natural beauty. Talbot County License ST-969-LEE PROPERTY FEATURES: Waterfront: Leeds Creek Dock: 100ft with 4ft MLW, water and electricity. Water Toys: 1 canoe is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Firepit: Firewood is not provided. Grill: Propane grill. Propane is provided. Pet Friendly: Owner will consider pets, call reservations at 443.664.4039 to inquire. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Crib - 1 / Queen - 1 / Queen - 1 / Queen - 1 / Bunk Bed - Single over Single - 2 / Single Bed - Twin Sized - 1 /

Master Shipwright

Sep 20 - 23

$1,420 night

Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience on Spa Creek. Four painstakingly renovated floors bring this home into this century without losing the shipbuilding history that surrounds it. The photos truly do not describe this incredible home. Walk into the front door into the street-side formal living room on the main level - comfortable and cozy. Pass through the formal dining room to a magnificent loft-type sitting room that opens to the lower-level sitting room. Floor-to-ceiling, two stories of windows bringing the glimmering Spa Creek inside! Wander down the waterside staircase (there are two, one at the main entrance and this one) into yet another comfy lounge space. The lower level sitting room sits beneath the main level sitting room and shares the splendor of two-storied windows. Proceed into the family room and enjoy the big comfy seating looking out to the patio. There is also a beautiful big dining table here. The kitchen is a large space off of the family room with an island and casual dining table embraced by a fireplace. Unique tile work, lots of counter space, and quality appliances provide you with everything you need and beyond to create and enjoy a family dinner. It features a gas stovetop, oven, microwave, large double-door refrigerator with drawer freezer and drink station, Keurig coffee maker, dishwasher, toaster oven, and all of the pots, pans, and dishware you need for memorable family gatherings. There are three unique dining areas in this home! The cozy, warm kitchen dining area is perfect for casual dining and offers to seat everyone. The formal dining room on the main level offers beautiful views with pre or post-dinner cocktails on the adjoining balcony. The lower-level family room also boasts a long fabulous dining table for a casual meal and game night. Walk out your doors to the patio, lawn, and water’s edge which has a dock for your boat and water toys. From the top down, the main-level balcony features two cushioned chaises and a gorgeous fire table surrounded by more Adirondacks. The lower-level walkout opens to a stone patio with chairs, a lawn, and two deep water docks for your boat and water toys. Additionally, a propane grill is available for warm-weather barbecues. THINGS TO KNOW

Windward Cove

Grasonville, MD, US

4 Bedrooms • 8 Guests

$1,024 night

Nestled in the charming village of Grasonville, Windward Cove offers an idyllic retreat for those seeking a blend of luxury and serenity. This stunning four-bedroom, three-bathroom waterfront home comfortably sleeps up to eight, making it perfect for families or groups of friends. The spacious layout includes an inviting living room with a gas fireplace, perfect for cozy evenings by the fire. The kitchen is a chef’s dream, fully equipped with modern appliances including a refrigerator with an icemaker, a dishwasher, and a Keurig coffee maker, ensuring you have everything needed for a comfortable stay. The bedrooms are generously sized and thoughtfully designed. The primary suite is located on the main floor, featuring a luxurious king bed and an en-suite bathroom with a luxurious bathtub. Two additional queen bedrooms share a hall bathroom, offering both privacy and convenience. An upper-level bedroom provides a quiet retreat with its own en-suite bathroom. Outdoors, Windward Cove truly shines. The waterfront location on Little Greenwood Creek offers the perfect setting for fishing or simply enjoying the peaceful sounds of nature. A private dock with 1 tandem and 2 single kayaks allows for easy access to the water, while the backyard deck is ideal for barbecues and outdoor dining. The screened porch provides a perfect spot to unwind with a book or a glass of wine, while the grill is available for your cooking needs. The home also features a well-equipped lower-level recreation room with a pool table, ping pong table, and a sectional sofa, making it an excellent space for games and relaxation. The sunroom offers additional seating and a tranquil space to enjoy the views. Additional amenities include a home gym, high-speed Wi-Fi, and cable TV, ensuring you have all the comforts of home. Located just a short drive from Annapolis, you can explore historic sites and enjoy the vibrant city life. Kent Island beaches are perfect for a day of sunbathing and swimming, while the Chesapeake Bay offers opportunities for boating and fishing. The Cross Island Trail is a must-visit for outdoor enthusiasts, providing miles of scenic routes to hike or bike. Windward Cove is not just a place to stay; it’s a place to create lasting memories. Whether you’re looking to relax by the water, explore the local attractions, or enjoy some friendly competition in the game room, this home offers the perfect setting for your getaway. Book your stay at Windward Cove today and experience the best of Maryland’s Eastern Shore. PROPERTY FEATURES: Waterfront: Little Greenwood Creek Dock: 40ft dock with 2ft MLW. Water and electricity are available for guest use. Water Toys: 1 tandem kayak and 2 single kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Fireplace: Gas fireplace is available for guest use. Gym: Home gym is available for guest use. Game Room: Pool table and ping pong table are available for guest use. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Queen - 1 / Queen - 1 / King - 1 / Double - 2 /

The Jolly Roger

Crownsville, MD, US

4 Bedrooms • 12 Guests

Sep 30 - Oct 2

$1,165 night

Experience the Difference: Professionally Managed by iTrip Annapolis Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is open to guests and offers many water sporting opportunities during your stay! Nestled in the desirable quiet Arden on the Severn community. There are kids’ and adult kayaks, canoes, stand-up paddle boards, fishing poles and crab traps. There are plenty of life jackets in the meticulous boat house. Sit on the back deck with unobstructed water views of the Severn River through the new glass railing. The deck has plenty of seating, a dining table and a gas grill. Head inside the home to the living space on the main floor that stretches across the kitchen, family and dining rooms - all with MILLION DOLLAR WATER VIEWS. The Main Floor Master Bedroom has a King bed (split with individual controls), master bath with multiple shower heads, a bidet and a walk-in closet. There are two more guest rooms on the main floor with Queen beds that share a full bath in the hall. The lower level is perfect for families with a large guest room with Queen Bed, a full bath and bunks for 4 kids or teens. Additional outdoor living space includes a large back yard, downstairs covered patio and a built-in firepit. The home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. SLEEPING ARRANGEMENTS 4 BR / 3 BA / Sleeps 8 adults and 4 kids/teens in bunks: Main Floor Suite: -King bed (Split with individual controls) -Private Bathroom with Shower, bidet and vanity -Large walk-in closet Bedroom 1 on Main Floor: -Queen bed -Full Hall Bath Bedroom 2 on Main Floor: -Queen bed -Full Hall Bath Bedroom on lower level: -Queen Bed -Full Hall Bath Bunk Room on lower level -2 Bunks (4 Twin beds) -Full Hall Bath HIGHLIGHTS: -Wrap-around deck with glass railing and water views a dining table and plenty of seating -Water access from private pier on the Severn River -BBQ Gas grill (propane tank provided) -Spacious kitchen with stainless steel appliances -Covered Patio on lower level -Firepit -Adult and kid kayaks (Life jackets provided) -Lower level recreation room with foosball and indoor/outdoor ping pong table and TV -Dining room table seats 10-12 -High Speed Internet and WiFi -Smart Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full Laundry room with washer & dryer located inside the home -Dogs allowed with $150 non-refundable fee paid prior to checkin Property Distance to: -Downtown Annapolis – 13 miles -U.S. Naval Academy – 13 miles -Washington, DC – 32 miles -Baltimore - 25 miles *Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. License: 000327

8 Mi to Dover Motor Speedway! Dog-Friendly Retreat

Dover, DE, US

3 Bedrooms • 6 Guests

Aug 26 - 28

$149 night

Welcome to this charming and modern townhouse located in the heart of Wyoming, Delaware. This two-year-old end unit townhome offers an open concept layout and is situated in a peaceful community, providing a tranquil retreat for your vacation. The property features a lovely patio and a fenced-in yard, perfect for enjoying the outdoors in privacy and comfort. Create everlasting memories with your loved ones at this fantastic two-year-old townhouse! -- THE PROPERTY -- 2024943770 | LL-00265 Guests will appreciate the convenience of a power outlet by the driveway, allowing for easy charging of electric vehicles during their stay. Inside, you'll find a range of amenities to ensure a comfortable and enjoyable visit, including high-speed internet, central AC, a washer/dryer, and a fully equipped kitchen with modern appliances such as a fridge, stove, oven, dishwasher, microwave, and coffee maker. This pet-friendly townhouse offers a variety of sleeping arrangements, including a king bed, queen bed, double bed, and cozy living spaces with a TV for entertainment. Relax in front of the fireplace, stream your favorite shows on Netflix, or enjoy the convenience of a wireless router for all your online needs. -- THE LOCATION -- Explore the surrounding area and take advantage of the numerous attractions and activities nearby, from horseback riding and hiking to water parks and winery tours. Whether you're seeking outdoor adventures or cultural experiences, Wyoming, Delaware, offers something for everyone. Book your stay at this delightful townhouse today and make unforgettable memories in this charming town! This end-unit retreat boasts a tranquil location in a quiet community in Wyoming, DE, and is close to many great restaurants, supermarkets, and attractions, including Brecknock County Park, Spence's Bazaar, Dover Par 3 & Driving Range, Firefly Music Festival, Dover Motor Speedway, Air Mobility Command Museum, and Bombay Hook National Wildlife Refuge. The Vacation rental is conveniently located only about an hour from Philadelphia and 2 hours from Washington DC -- 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/ $200 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Quiet hours are from 10:00 PM to 8:00 AM Licence number: LL-00265

Baltimore Abode, Walk to Cross Street Market!

Baltimore, MD, US

3 Bedrooms • 10 Guests

Aug 29 - 31

$389 night

Experience Charm City at its finest when you book a stay at this chic townhouse. Offering a cozy patio, a private yard, and a full kitchen, this 3-bedroom, 2-bath gem serves as the ideal home base for your next trip to Maryland. Enjoy action-packed days exploring the nearby museums and strolling through Federal Hill Park, then head to M&T Bank Stadium to spend the night cheering on the Ravens. With its inviting interior and prime location, this property is guaranteed to meet your every need! -- THE PROPERTY -- STR License: 956094 | 2,160 Sq Ft | Walk to Restaurants & Bars | Pet Friendly w/ Fee Make memories that will last a lifetime at this spacious Baltimore property — fit for families, friends, and adventure seekers alike. Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Living Room: 2 Queen Sleeper Sofas KITCHEN: Fully equipped w/ stainless steel appliances, coffee bar w/ Keurig, dishware & flatware, toaster, knife set, blender, cooking basics, ice maker, wet bar INDOOR LIVING: Smart TVs, fireplace, dining table, ceiling fans, board games, books OUTDOOR HANGOUT: Patio, private yard GENERAL: Free WiFi, towels & linens, complimentary toiletries, central A/C & heat, keyless entry, hair dryer, hangers, iron & board, trash bags & paper towels FAQ: Doorbell camera (facing out), stairs required for entry, bathroom & bedroom access, pet fee (paid pre-trip) PARKING: Free street parking (first-come, first-served) -- THE LOCATION -- AREA HIGHLIGHTS: Cross Street Market (0.2 miles), National Aquarium (1.7 miles), Baltimore Harbor (2.5 miles), The John Hopkins Hospital (3.0 miles), John Hopkins University (4.5 miles), The Maryland Zoo in Baltimore (4.6 miles) VENUES (~1 mile): Hippodrome Theater, Royal Farms Arena, Baltimore Convention Center, Oriole Park at Camden Yards, M&T Bank Stadium MUSEUMS: Maryland Science Center (0.7 miles), American Visionary Art Museum (0.8 miles), Baltimore Museum of Industry (0.9 miles), Historic Ships in Baltimore (1.4 miles), Port Discovery Children’s Museum (1.6 miles), The Walters Art Museum (1.8 miles), Washington Monument & Mount Vernon Place (1.9 miles) OUTDOOR OPTIONS: Federal Hill Park (1.1 miles), Pierce’s Park (1.8 miles), Patterson Park (3.5 miles), Canton Waterfront Park (5.8 miles), Patapsco Valley State Park (8.7 miles), North Point State Park (14.9 miles) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (10.2 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 - Pet friendly w/ $200 fee (+ fees & taxes) - Pets are not to use the backyard as an area to relieve themselves - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Your safety matters. This property features a doorbell camera, facing the entryway. It records video and sound and is motion-activated but does not look into any interior spaces - NOTE: The property requires stairs for entry and access to the bathrooms and bedrooms Licence number: STR-2704

1 Mi to Dtwn: Townhome w/ Patio in Baltimore!

Baltimore, MD, US

$228 night

Great for Groups | Pet Friendly w/ Fee | Convenient Location Near Hot Spots Your Baltimore escape awaits at this at this spacious 4-bedroom, 3-bath vacation rental. Cheer on your favorite team at Camden Yards or take a water taxi across the Patapsco River before enjoying a stroll Downtown. There will be something to enjoy for every member of the family! Afterward, unwind at the townhome by whipping up a mouthwatering meal in the kitchen and dining al fresco on the patio! -- THE PROPERTY -- STR-162969 - EXPIRES 11/11/26 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed, 1 full sleeper sofa - Bedroom 3: 1 full bed - Bedroom 4: 1 full bed INDOOR LIVING - 5 flat-screen TVs - Dining table - Jetted tub OUTDOOR LIVING - Patio - Outdoor seating & dining KITCHEN - Stove/oven, refrigerator, dishwasher - Drip coffee maker (starter coffee provided), microwave - Trash bags & paper towels GENERAL - Free WiFi - Central A/C & heating - Washer/dryer - Linens/towels & hair dryer FAQ - Pet fee (paid pre-trip) ACCESSIBILITY - 3-story townhome, 2 steps to enter - Bedroom & full bathrooms on 1st floor PARKING - Free street parking (first-come, first-served) -- THE LOCATION -- - 1 mile to Downtown Baltimore & the National Aquarium - 2 miles to Oriole Park at Camden Yards & The Baltimore Convention Center - 5 miles to The Maryland Zoo in Baltimore - 0.7 miles to the Baltimore Water Taxi - 0.8 miles to The Johns Hopkins Hospital - 11 miles to Baltimore/Washington Int'l Thurgood Marshall 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/ $50 fee (+ fees & taxes, 5 pets max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 3-story townhome requires 2 steps to enter. It offers a bedroom and full bathrooms on the 1st floor Licence number: STR-162969

Pet Friendly Water View Cottage

Pasadena, MD, US

2 Bedrooms • 4 Guests

$240 night

Escape to our updated 2-bed, 2-bath cottage in a charming Pasadena water privileged neighborhood. Comfortably sleeping 4, this bright getaway features a fully equipped kitchen, a private patio, and easy self-check-in. Perfectly located just a 20-minute drive from both Annapolis and Baltimore, it’s an ideal base for exploring the Chesapeake Bay area. Enjoy a walkable neighborhood with local dining and parks nearby. Step through the cheerful yellow front door into a bright, open-concept living space designed for relaxation. This updated cottage offers a comfortable and stylish retreat. Living Area: Relax on the comfy sectional sofa and stream your favorites with the provided Netflix access Kitchen & Dining: A full kitchen with stainless steel appliances and granite countertops has everything you need for home-cooked meals. Bedrooms: Two cozy bedrooms, each furnished with a comfortable queen-sized bed. Bathrooms: Two full bathrooms; one with a walk-in shower and the other with a tub/shower combination. Laundry: An in-unit washer and dryer are available for your convenience. Outdoor Space: Your private back patio features a wicker sectional for lounging after a day of adventure. Guests will have private access to the entire cottage, including the private back patio and hot tub. Enjoy a seamless and flexible arrival with our self-check-in system. Self Check-in: Use the smart lock for easy entry. Unique Code: You will receive a unique door code for the duration of your stay. Arrival instructions are sent via email multiple times during the week leading up to your stay. A few important details to ensure a smooth stay: Digital Renter Agreement: You MUST sign the digital renter agreement after you book. This is required to receive your arrival instructions. Arrival Instructions: Your unique door code and check-in details will be sent via email, but only AFTER the renter agreement is signed. Check Your Email: Please be sure to check your spam/junk folder if you do not see these important emails in your inbox. Registration Number: 000741 License number: STR00741

Pasadena Retreat

Pasadena, MD, US

4 Bedrooms • 8 Guests

Aug 24 - 31

$1,352 night

Whether you’re planning to explore Annapolis, Baltimore, or Washington, DC, this four-bedroom home in Pasadena perfectly fits the bill. Enjoy a living space that’s been renovated from top to bottom and magnificent outdoor spaces that include a private pool, a hot tub, and an expansive backyard. Originally a farmhouse that dates back to 1953, this two-story home sits on nearly an acre of land 14 miles southeast of BWI. It’s a great spot if you’re visiting the United States Naval Academy (13 miles south), Baltimore’s Inner Harbor (20 miles north), or our nation’s capital (40 miles west). Let’s begin in the wonderful backyard, fully fenced so your kids and dogs can roam safely. After a day of fun-filled excursions, you can take a dip in the pool, unwind in the bubbling hot tub, or simply push your children on the swings hanging from the trees. Light the gas grill on the deck for an evening barbecue, gather for dinner at one of several tables outside, and tell stories by the firepit once the sun goes down. Thoughtful updates have expanded the home’s footprint to 2,900 square feet. The elegant kitchen anchors the main level, offering stainless steel appliances (including a wine fridge and a dishwasher), a large island with bar seating, and a country dining table. For movie or game nights, gather in the living room or the cozy den, both with TVs. There are two primary suites - one downstairs, one upstairs, and each with its own bathroom. The two guest rooms share a bathroom upstairs. Other family-friendly amenities of this house include a Pack ’N Play, a high chair, baby gates, and a laundry room. THINGS TO KNOW The pool is open from May 20 until Labor Day.

Spacious Luxe USNA Home - Pool, Hot Tub, Grill

5 Bedrooms • 14 Guests