Large group vacation rentals in Grasonville, MD

Become enveloped by Maryland hospitality when you stay at ‘The Winchester,’ a gorgeous home right on the water. With stunning features both inside and out, this 3-bedroom, 2-bath vacation rental has everything you need for a relaxing trip to the East Coast. Relax in the bright interior and enjoy the fully equipped kitchen or the Smart TVs. You can enjoy the seasonal pool or head out onto the water for some outdoor fun. The surrounding towns also have lots to do from dining to shopping and more! -- THE PROPERTY -- Walk to Beach & Playground | 2,000 Sq Ft | Dock | Stainless Steel Appliances Bedroom 1: King Bed | Bedroom 2 (Murphy Room): Queen Murphy Bed | Bedroom 3 (Treehouse): Queen Bed, Twin Bunk Bed OUTDOOR LIVING: Private pool (Memorial Day - Labor Day, depth 4'), gas grill, furnished patio, outdoor dining area, fire pit (firewood provided), gazebo, life vests, private pier w/ boat dock, crab traps & live box INDOOR LIVING: Smart TVs, 2 dining tables, gas fireplace (available in colder months), walk-in closet KITCHEN: Breakfast bar w/ seating, dishwasher, refrigerator, stove/oven, microwave, drip coffee maker, Crockpot, blender, toaster, spices, cooking basics, dishware & flatware, high chair GENERAL: Free WiFi, central A/C, linens/towels, washer/dryer, ceiling fans, hair dryers, hangers, iron/board, trash bags & paper towels, 3 exterior security cameras FAQ: Stairs required for access, bedroom & bathroom on 1st floor PARKING: Driveway (4 vehicles), carport (1 vehicle) -- THE LOCATION -- OUTDOOR ADVENTURE: Winchester Creek (on-site), Long Point Park (1.1 miles), Jackson Creek Landing (1.2 miles), Grasonville Park (1.2 miles), Ewing Pond Park (2.0 miles), Kent Narrows Public Boat Ramp (3.3 miles), Ferry Point Park (3.4 miles), Queenstown Harbor Golf (4.9 miles), Old Love Point Park (7.0 miles), Terrapin Nature Park (7.6 miles), Washington Hunters Oak Country Club (7.9 miles), Mowbray Park (8.2 miles), Queen Anne's County Parks (8.8 miles), Matapeake Park (9.3 miles), Kentmorr Marina (12.2 miles), Sandy Point State Park (12.7 miles) AREA ATTRACTIONS: Watermen's Monument (2.4 miles), Chesapeake Bay Environmental Center (2.6 miles), Stevensville Historic District (6.4 miles), Old Wye Mill (9.5 miles), Chesapeake Bay Maritime Museum (31.9 miles), Six Flags America (38.0 miles) Washington D.C. (49.1 miles): Arlington National Cemetary, Ford’s Theater, National Gallery of Art, Smithsonian National Air and Space Museum, Smithsonian National Museum of Natural History, United States Holocaust Memorial Museum, National Museum of African American History and Culture, Washington Monument, United States Capitol, World War II Memorial, Lincoln Memorial, Vietnam Veterans Memorial, Korean War Veterans Memorial GOOD EATS: La Piazza Pizza & Italian Restaurant (1.3 miles), Hunter's Seafood and Market (1.4 miles), Fisherman's Inn Restaurant (2.5 miles), The Narrows Restaurant (2.5 miles), The Jetty (2.5 miles), Bridges Restaurant (2.5 miles), Fisherman's Crab Deck (2.6 miles), Harris Crab House (2.6 miles), Adams Grille & Tap House Kent Island (4.3 miles) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (36.8 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: The property requires stairs to access - NOTE: Your safety matters. This property features 3 exterior security cameras: 1 camera is located on the front of the house facing the door and pool area, 1 camera is facing the driveway entrance, and 1 camera is facing the rear side of the carport and driveway. The cameras are outward facing and do not look into interior spaces. The cameras actively record both video and sound

Ideal felicity and perfection! This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a flow-through living, entertaining and dining area and a generous foodie inspired kitchen. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, direct access to an expansive deck, and water views. The wonderfully secluded property boasts a beautiful built-in swimming pool, private dock, and paved ramp to launch your boat. While this rental provides wonderful privacy, it’s also a five minute car ride from the Queenstown Outlets, and a ten minute car ride from several popular waterfront restaurants, farmers markets, and grocery stores. You will love this waterfront vacation home! Well placed in a sought-after Queen Anne’s County neighborhood. This unique home will book fast! PROPERTY FEATURES: Waterfront: Wye River Dock: Private dock with MLW 3’. Electricity is available for guest use. Guests are permitted to tie a boat to the dock. Boat Ramp: Private paved boat ramp onsite for boat launch. Water Toys: 2 adult kayaks and 1 adult paddle board are 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. Grill: Propane grill. Propane is provided. 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 / King - 1 / Queen - 2 / Bunk Bed - Pyramid | Single over Double - 1 /

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.

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 /

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 /

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

Discover the charms of Queenstown, Maryland, with a stay at this lovely 4-bedroom, 2.5-bath vacation rental! Packed with family-friendly amenities, this home has everything needed for a peaceful getaway with loved ones — including a spacious deck, a fully equipped kitchen, and a cozy living room with a fireplace. Spend your day strolling through Terrapin Nature Park, then return home for a cookout on the grill or a family game night around the dining table. -- THE PROPERTY -- 2,336 Sq Ft | Furnished Deck | Spacious Yard | Fire Pit Bedroom Suite: King Bed | Bedroom 2: King Bed | Bedroom 3: King Bed | Bedroom 4: Full Bed | Additional Sleeping: Pack 'n Play HOME HIGHLIGHTS: Smart TVs, electric fireplace, home gym, large dining table, board games, gas grill KITCHEN: Fridge, stove, dishwasher, Keurig/drip coffee maker, microwave, cooking basics, toaster, dishware/flatware, trash bags/paper towels, high chair GENERAL: Free WiFi, keyless entry, central heating & A/C, complimentary toiletries, linens/towels, washer/dryer, ceiling fans, hair dryer, iron/board FAQ: 2 external security cameras (facing out) ACCESSIBILITY: Multi-level home, 3 steps to enter, interior stairs required to access bedrooms PARKING: Garage (2 vehicles), driveway (8 vehicles), EV charger -- THE LOCATION -- OUTDOOR ADVENTURE: Queenstown Harbor Golf (6 miles), Ewing Pond Park (6 miles), Kent Narrows Public Boat Ramp (10 miles), Ferry Point Park (11 miles), Terrapin Nature Park (14 miles), Sandy Point State Park (20 miles) AREA ATTRACTIONS: Old Wye Mill (3 miles), Watermen's Monument (9 miles), Chesapeake Bay Environmental Center (9 miles), Stevensville Historic District (14 miles), Chesapeake Bay Maritime Museum (25 miles), Six Flags America (44 miles) WASHINGTON, D.C. (55 miles): Arlington National Cemetery, Ford’s Theater, National Gallery of Art, Smithsonian National Air and Space Museum, Smithsonian National Museum of Natural History, United States Holocaust Memorial Museum, National Museum of African American History and Culture, Washington Monument, United States Capitol, World War II Memorial, Lincoln Memorial, Vietnam Veterans Memorial, Korean War Veterans Memorial AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (48 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 multi-level home requires 3 steps to enter and interior stairs are required to access all the bedrooms - NOTE: Your safety matters. This property features 2 external security cameras: 1 camera located on the front porch facing the front entry and 1 camera located on the garage facing the entrance. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Private Pool w/ Waterfall | Scenic Sunroom | 1,750 Sq Ft Your slice of paradise awaits at this waterfront vacation rental in Stevensville, MD! Spend your days soaking up the sun by the pool while enjoying panoramic views of the bay. After hitting the beach at Sandy Point State Park, return to the 3-bedroom, 2-bath home and watch the sunset as you sip a refreshing drink by the fire. This property also boasts multiple outdoor dining tables, perfect for enjoying a meal as the sun sets! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed  - Bedroom 2: 1 queen bed, 1 lofted twin bed - Bedroom 3: 1 queen bed - Living Room: 1 queen sleeper sofa - Sunroom: 1 queen sleeper sofa OUTDOOR LIVING  - Private pool (unheated) - Dining area w/ umbrella - Gas fire pit, lounge seating - Outdoor shower - Dock - Community park & boat ramp (kayaks & paddle boards) INDOOR LIVING  - 5 Smart TVs, Sonos speaker - 2 dining tables - Picture windows - Ceiling fans KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, wine cooler - Keurig coffee maker (bring your own coffee) - Cooking basics, dishware/flatware - Trash bags/paper towels GENERAL   - Free WiFi  - Central & mini-split air conditioning/heat - Linens, towels, shampoo, conditioner, hair dryer - Washer/dryer, iron/board, hangers FAQ - 4 exterior security cameras (facing out) ACCESSIBILITY - Single-story home, 3 steps to enter PARKING - Driveway (6 vehicles) -- THE LOCATION -- - 2 miles to various restaurants - 3 miles to Chesapeake Bay Beach Club - 9 miles to Sandy Point State Park - 6 miles to Kent Narrows, MD - 16 miles to Annapolis Naval Academy - 36 miles to Baltimore/Washington 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 ADDITIONAL INFORMATION - This single-story home requires 3 steps to enter - The on-site boats, pavilion, and outdoor kitchen area are not available for guest use - Your safety matters. This property features 4 exterior security cameras: 1 camera is by the front door facing the front entrance, 1 camera is on the left side of the home facing the side yard, 1 camera is by the back door facing the back entrance, and 1 camera is on the back of the home facing the backyard. The cameras are outward facing and do not look into interior spaces. The cameras are activated by motion and will record video and sound while guests are in residence

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 /

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.

Experience the Difference: Professionally Managed by iTrip Annapolis Kent Island Chesapeake Bay Cottage with Private Pool & Sunset Views Welcome to your dreamy poolside getaway! This charming summer cottage offers a private pool and breathtaking views of the Chesapeake Bay. The oversized wrap-around deck is perfect for sipping morning coffee or enjoying stunning Bay sunsets. (Pool is open April through October.) Sleeps up to 11 Guests 3 Bedrooms • 3 Bathrooms • Ideal for up to 8 adults + 2-3 children Main Floor (Upstairs): King Suite Bedroom: King bed + En Suite Full Bath Twin Suite Bedroom: 2 Twin beds + En Suite Bath Open Family Room: Queen Sleeper Sofa + Full-size Daybed Lower Level: Private Guest Room: Queen Bed + Full Hall Bath Sleeping/Family Room: Full Bed + Twin Daybed Highlights: Private Backyard Pool (open April 23–October) Wrap-Around Deck with Chesapeake Bay Views Multiple Dining Areas: Indoor Dining Table (seats 8) Deck Dining Table (seats 6) Poolside Table (seats 6) Front Yard Table (seats 6) Weber Propane Grill High-Speed Internet & WiFi 3 Flatscreen TVs 3 Bicycles for guest use NASA-developed AquaSpace Water Filter Luxury Linens + Complimentary Toiletries Starter Kit Full Washer & Dryer Circular Driveway Parking for 4–5 Vehicles Note: Home uses window A/C units (no central air) Keyless Entry through garage door keypad Location: Downtown Annapolis – 19 miles (~25 mins) U.S. Naval Academy – 19 miles Washington, DC – 48 miles Baltimore – 43 miles House Rules: Minimum Age: One guest must be at least 25 years old No Smoking, No Pets, No Parties or Events Respect the home as if it were your own – this is a cherished private residence. Please be courteous to neighbors and observe quiet hours. Check-in: 4:00 PM Check-out: 11:00 AM Experience the Difference: Professionally Managed by iTrip Annapolis

This short-term rental has an occupancy of 16 individuals with a max. of 12 guests being 18 years or older. Experience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 6-bedroom, 5.5-bath waterfront home, just minutes from downtown Annapolis! The main level is designed for entertaining, featuring a great room with an open kitchen concept, an oversized island with seating for six, and a cozy seating area. Enjoy meals with family and friends in the light-filled sunroom that comfortably accommodates twelve. Discover the secret Pirate’s Cave hiding next to the laundry room, a fun-filled game room with a big screen TV equipped with table tennis, darts, air hockey, and foosball—perfect for all-day entertainment with family and friends. The brand new 20x40 swimming pool offers a basketball hoop and a relaxing tanning ledge where you can watch the sun set behind the Bay Bridge. The pool area is adjacent to a covered gazebo deck, an ideal spot for enjoying a crab feast from one of the local restaurants or a glass of wine. The property also features a new private pier, providing an idyllic setting for crabbing, fishing, and bird watching. Spend tranquil mornings casting a line or catching crabs, and enjoying the serene beauty of local wildlife. The pier offers ample seating for relaxation and is the perfect vantage point for observing the stunning Chesapeake Bay sunsets over the bridge. Gather around with drinks on the rear deck outfitted with a gas fire pit and plenty of seating. Or seat around the fire pit in the backyard making smores and watching the night sky. Younger guests will be thrilled by the pirate-inspired treehouse and play area, featuring a climbing wall, pirate plank, swings, slide, hammock, and treehouse! PROPERTY FEATURES: Waterfront: Chesapeake Bay. Pool: 20 x 40 private pool with a basketball hoop. Swimming pools are open from May 22 - October 15. Be sure to bring your own pool towels. Dock: 150 ft x 6 ft private dock for fishing and crabbing. Game Room: Billiards, ping pong table, air hockey, foosball, and darts Outdoor activities: cornhole, basketball hoops and Tree house. Grill: Propane grill. Propane is provided. Fireplaces: Outdoor gas fireplace table. Pet Policy: Pets are not permitted. WiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

Relax and unwind at this spa-like luxury waterfront estate. Located on the Chesapeake Bay, this newly constructed vacation rental features 5 bedrooms, 5 bathrooms, and opulent interior design with expansive living areas. Are you looking to entertain? You have come to the right place. Wow your guests with the cuisine you will craft in the chef-inspired kitchen that boasts stainless-steel appliances, an enormous kitchen island and serve them at the grand dining table with panoramic sunset views. After dinner you and your guests can enjoy the pool or hot tub while sipping cocktails and talking about how you never want to leave. Natural lighting creates the perfect ambiance in any of the 5 private suites. Each suite also offers its own ensuite. Reap the benefits of neighborhood living in this sought-after part of Queen Anne’s County. Just a 3 - 5 minute drive to the Cross Island Trail, Blue Heron Golf Course and Driving Range, and the Mowbray Park tennis and pickleball courts and 10 - 15 minutes from some of the best restaurants, shopping, cafes, bars, wineries, nightlife, and mom-and-pop shops. All the perks of Queen Anne’s County living are an easy drive away. Be prepared to have your breath taken away. Book your luxury getaway today! PROPERTY FEATURES: Waterfront: Chesapeake Bay Dock: Private dock with power and water available for guest use. Pool: Private pool. Swimming pools are open from May 15 - October 15. Hot Tub: Hot Tub available for guest use from May 15 - October 15. Firepit: Propane provided. Elevator: Available for guest use. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: Upon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.

This short-term rental has an occupancy of 14 individuals with a max. of 6 guests being 18 years or older. Experience the ultimate getaway at this gorgeous Kent Island waterfront! This 4,600 square-foot, 6-bedroom, 4.5-bathroom Long Creek waterfront retreat on over 2.6 acres of private land is perfect for your family vacation. The main level features a beautifully renovated kitchen, a dining room seating up to 12, and a breakfast area with stunning water views and sunrise vistas. This property features two entertainment indoor areas for all ages. The lower level of the main house serves as a lively entertainment hub, complete with a full bar and a billiards table, perfect for evening relaxation or friendly competition. When you step out to the backyard, you’ll find the huge detached game lounge, housing a variety of games including table tennis, air hockey, foosball, cornhole, darts, and arcade basketball hoops. An 86-inch screen TV with lounge seating provides the perfect spot for watching your favorite sports. For those looking to stay active, the property features a pickleball court along with an outdoor basketball hoop, and a peaceful sunroom for stretching and yoga in the morning. Enjoy a bike ride to a nearby trail and uncover the serene beauty of Kent Island. Lighthouse Haven offers a spacious upper deck and patio, an in-ground pool, an outdoor kitchen under the pavilion, and a private pier for kayaking, paddle boarding, crabbing, and fishing. Enjoy bird watching, then gather around the fire pit for storytelling and s’mores under the stars. This secluded vacation rental is only a 10-minute car ride from charming waterfront restaurants, bars, farmers’ markets, shopping, and grocery stores near the Chesapeake Bay bridge. Book your stay today and create unforgettable memories! PROPERTY FEATURES: Waterfront: Long Creek  Dock: 140ft x 6ft private dock with MLW 4 ft. Electric and water, including a sink available for guest use. 2 crab traps are provided. Guests are not permitted to tie a boat to the dock.  Water Toys: 1 two-person kayak, 1 tandem kayak, and 1 stand up paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.  Pool: 16 x 32 private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.  Fireplaces: Outdoor gas fireplace table on the deck is available for guest use.  Firepit: Outdoor firepit available for guest use.  Grill: Propane grill. Propane is provided.  Land Toys: Pickleball court (with paddles & balls), outdoor Basketball hoops, billiard, table tennis, foosball, Dart Board, cornhole, Arcade basketball hoop, available for guest use. 2 adult bikes. WiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

New Hot Tub available late June 2026. Relax and unwind. Located on the Chesapeake Bay, this charming vacation rental features 3 bedrooms, 2 bathrooms, and a renovated kitchen that boasts exquisite high-end granite countertops, a gas range, and stainless steel appliances.. An extra full bath, strategically placed, offers easy access from the pool and outdoor areas. The open floor plan in the living areas, providing a cozy spot to enjoy the mesmerizing views of Kent Island’s waterways and seasonal bird migrations. Watch the sunrise over the bay. Dine indoors or al fresco, the choice is yours. Reap the benefits of neighborhood living in this sought-after part of Queen Anne’s County. Just a 3 - 5 minute drive to the Cross Island Trail, Blue Heron Golf Course and Driving Range, and the Mowbray Park tennis and pickleball courts and 10 - 15 minutes from some of the best restaurants, shopping, cafes, bars, wineries, nightlife, and mom-and-pop shops. All the perks of Queen Anne’s County living are an easy drive away. Book your getaway today! PROPERTY FEATURES: Waterfront: Eastern Chesapeake Bay Dock: Private dock with 130 ft of shoreline, 4.6 ft MLW with electric at dock but no water. Guests are not permitted to tie a boat to the dock. Water Toys: 4 Kayaks, and crabbing gear available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Hot Tub: New Hot Tub available for guest use late June 2026. Land Toys: Corn hole is available for guest use. Grill: Charcoal grill. Charcoal is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

One Of A Kind! Tranquil and timeless, Fairview is among the great historic estates of Talbot County. Offering a total of 6 bedrooms, 4 full baths and 2 half baths, the home and property provide ultimate peace and privacy. The waterfront estate is located on the Eastern Shore and sits at the end of a peninsula on the Miles River, a 12.9-mile-long tributary of the Chesapeake Bay, and is equidistant to the towns of Easton and St. Michaels. The estate’s picturesque grounds encompass 74 acres of private parkland, 19th-century formal gardens, and 1,500 feet of shoreline with a private beach. With 3 private golf holes, an 20’ x 47’ pool, basketball court with hoop, tennis court, a gym, and 50 acres of backyard, this vacation experience offers excitement for the whole family. Fairview Estate with its serene and private setting offers a rare rental opportunity to enjoy the best that the Eastern Shore has to offer. Talbot County STR License STN-26-31 PROPERTY FEATURES: Waterfront: Miles River with 1500’ of shoreline. Dock: Floating dock. Guests are not permitted to tie a boat to the dock. Water Toys: 1 double and 1 single kayak are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 47’ x 20’ private pool. Swimming pools are open from May 15 - October 15. Heat is available for an additional fee. Please contact us if you want to add this option. Pool House: Pool house with bathroom and shower available for guest use. Private Beach: Private beach with floating dock and water toys available for guest use. Grill: 2 propane grills. Propane is provided. Golf Course: Three hole (Par 3) golf course and practice area. Bring your own clubs. There will be practice balls available for guest use. Exercise Room: Exercise room available for guest use. Fire Pit: Available for guest use. Land Toys: 8 bicycles are available for guest use. Pet Friendly: This is a pet friendly rental. WiFi: Included for guest use. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: An ESVR representative greeting you upon arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.