House vacation rentals in Chincoteague Bay

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Top-rated house rentals in Chincoteague Bay

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Superhost

A spacious outdoor deck overlooks a serene waterfront view, featuring several white adirondack chairs arranged for relaxation. The lush green lawn leads down to the water, where a fire pit is positioned nearby, providing a peaceful gathering spot.

Home in Ocean City

4.78 out of 5 average rating, 23 reviews

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Guest favorite

An open living area showcases a comfortable sectional sofa and two blue armchairs surrounding a light coffee table. The adjoining kitchen features white cabinetry and modern appliances, while a dining area with dark wood furnishings is visible in the background, emphasizing a spacious and inviting layout.

Home in West Cape May

4.98 out of 5 average rating, 112 reviews

West Cape May Beach House

Well maintained home, centrally located and within walking distance from the center of town, great restaurants, retail shops, food stores and the Washington Street mall. The beach is just 12 blocks away which makes for an enjoyable bike ride. The large driveway offers plenty of parking. During the summer season, the home is available by the week from Saturday to Saturday. Check-in time is 2 pm and check out-time is 10am. Throughout the rest of the year, shorter duration stays are available.

Guest favorite

A serene balcony features a small round table and two elegant chairs, providing a scenic view of Carr's Creek. The smooth stone flooring complements the bright surroundings, while the water glistens in the sunlight, reflecting the natural beauty of the area.

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Top guest favorite

The exterior of a ranch-style cottage is displayed, featuring a welcoming front porch with two white rocking chairs. Colorful flower beds and a manicured lawn enhance the space. A paved pathway leads from the driveway to the porch, framed by lush greenery and decorative elements.

Home in Cape May

4.96 out of 5 average rating, 27 reviews

The Adria Bayside Cottage

Nestled in a neighborhood yet close to the Cape May-Lewes Ferry (summer concerts; restaurant) and the Bay beach (walking distance), this stylish, modern farmhouse/coastal rental boasts hardwood floors, new paint, all new amenities, fixtures and furnishings. Linens are provided (except beach towels) with sleeping capacity up to 5 persons. Four Cape May beach tags are also provided. Beach chairs and umbrellas are also provided housed in an on-property shed where your bikes can also be secured.

Superhost

The exterior of the historic Thomas Harrison House is depicted, showcasing its white clapboard siding and red metal roofs. A large covered porch is visible on the right, along with a well-maintained lawn and trees providing shade.

Home in Saint Michaels

4.83 out of 5 average rating, 78 reviews

Harrison House - in Town and on St Michaels Harbor

The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels, rented as such since 1992. It is the only large (6 bdrm) vacation rental in Town. The house is located on the harbor (spectacular water views) and the town park in the center of St. Michaels - walking distance to all museums, parks, shops, stores, restaurants, town pool, tennis courts and library. Rates vary by day of the week and season. Discounts for week stays or "last minute" bookings.

Top guest favorite

A single-story cottage is depicted, featuring a light-colored exterior and a welcoming front porch. A manicured lawn surrounds the home, while the driveway leads to the entrance. The building's design emphasizes a classic style with large windows allowing natural light.

Home in Lower Township

4.95 out of 5 average rating, 22 reviews

1 Block to the Bay-Amazing Sunsets!

Luxury cottage walkable to the beach and Harpoon’s on the Bay. ★ “Amazing stay! The house is beautiful and impeccable. We definitely recommend booking!” ☞ Fully-equipped kitchen w/ high-end appliances ☞ Private parking in 2 driveways ☞ Only 1 Block away to the beach & amazing sunsets! ☞ New spacious deck w/adirondack chairs ☞ Beach chairs, umbrella, beach cart & cooler ☞ Covered Patio w/ Propane Grill (grilling utensils provided) ☞ High-Speed WiFi & Streaming TVs ☞ Enclosed outdoor shower

Guest favorite

A historic brick duplex features a welcoming front porch with rocking chairs, framed by black shutters. The well-maintained exterior is complemented by a landscaped yard, creating a charming entryway. Soft evening light enhances the inviting appearance of the home.

Home in Cape Charles

4.94 out of 5 average rating, 116 reviews

Bakery Next door! Beautiful Renovations

Nectarine 13 is centrally located, century old brick duplex is newly renovated and ready for guests. It's a short walk next door to the Coastal Baking Company to get your freshly baked cinnamon roll. Sit on the front porch and enjoy the calm, quaint, historic town of Cape Charles. Take a swim in the bay or cast your poles from the dock just blocks down Main Street. Central Park, is a short stroll, and a great place for a picnic while the kids enjoy the playground. Golf carts for rent as well.

Top guest favorite

The exterior of a townhouse highlights a light-colored facade with multiple windows and balconies. The driveway curves around well-maintained greenery, accompanied by lampposts and neatly trimmed bushes, creating an inviting approach to the home.

Home in Rehoboth Beach

5 out of 5 average rating, 41 reviews

5 BR Townhouse w/ private elevator-Rehoboth Beach

This townhouse features 5 bedrooms and 3.5 bathrooms, elevator, and plenty of parking. Pets are allowed with a fee, and you can access two gyms. We offer complimentary sheets and towels. Community pools are available from Memorial Day through Labor Day. It is located in a gated community five miles from downtown Rehoboth Beach. Rentals booked from Labor Day to Memorial Day are non-refundable if canceled within 30 days of the rental date. The HOA requires a short-term lease agreement.

Guest favorite

A single-story cottage is surrounded by a white picket fence, showcasing a well-tended front yard with greenery and flowers. The front porch features a screened area, while the exterior is painted in light tones, complemented by a peaked roof against a bright blue sky.

Home in Chincoteague

4.9 out of 5 average rating, 112 reviews

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

Superhost

A modern living area features a spacious gray sectional sofa complemented by a matching ottoman. A decorative tray with a 'Welcome' sign sits atop the ottoman. Light streams through a window, and a potted plant adds a touch of greenery to the space.

Home in North Cape May

4.86 out of 5 average rating, 111 reviews

Beautiful N.Cape May retreat blocks from the beach

A quaint beach house, a short walk to the bay, incredible sunsets, fishing and a fun beachfront restaurant and bar. Only a few miles to Cape May. Recently renovated with a large master suite, two additional bedrooms, two full baths and a well appointed kitchen. Completely modernized with all the essentials needed for an enjoyable stress free getaway in a quiet neighborhood in North Cape May. We will help make your vacation a great one in our wonderful home.

Guest favorite

The exterior of the house features a light grey siding with white trim and a balcony overlooking the street. A covered porch is accessible from the front steps, and a spacious driveway with gravel leads to the side of the house, where a storage shed is visible.

Home in Avalon

4.89 out of 5 average rating, 189 reviews

Adorable Avalon House with Pool

Sunny, Stylish & Now With a Pool (complete May 2025)! Just steps from an expansive park (hello tennis & pickleball!), a short walk to the bay or the beach, or cruise on our complimentary beach bikes. Booking Quick Hits for 2025: • April 18–MDW: Fri + Sat booked together • Summer: 1-week minimum • September: 2-night minimum • Otherwise: no minimum stay! Fresh sheets and bath towels included with your cleaning fee—just show up and relax.

Guest favorite

A spacious outdoor deck is furnished with stylish seating and a large dining table, set against a backdrop of lush green trees. The wooden deck extends into the yard, providing an ideal space for relaxation and entertaining in a serene environment.

Home in Lewes

4.96 out of 5 average rating, 129 reviews

Woodsey Beach House - Beach, Lake, Woods!

Beach? Check Cabin? Check Lake? Check Have it all at our home near the beach, in a beautiful wooded setting with a lake view! Quiet neighborhood makes you feel right at home. Newly renovated with new appliances and furnishings. The house has an upside-down layout, so most of the living spaces, including the kitchen, dining, and living rooms are on the second floor. The home is unique, bright and comfortable.