House vacation rentals in Chesapeake Bay

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Top-rated house rentals in Chesapeake Bay

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Superhost

Home in Ocean City

4.79 out of 5 average rating, 24 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

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

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

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

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.

Superhost

Home in Cape May

5 out of 5 average rating, 3 reviews

The Spotted Sandpiper 4 bed/2.5 bath pet friendly!

Pet friendly! Ideal location, 104 Atlantic Ave in West Cape May! Our 2,600 sq ft. 4 bedroom, 2.5 bath home is tucked away on a quiet street but in the heart of the West Cape May restaurant district. 1 block from West Cape May restaurants, a short 10 minute walk to the Mall, Or beach. Short bike ride to wineries or lighthouse. Driveway for up to 4 cars and huge wrap around porch. 4 bedrooms for 11 guests with 2 Kings, 1 Queen, 5 Twins, all located on the 2nd floor. Fenced Yard, grill, patio.

Top guest favorite

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

Home in Cape Charles

4.94 out of 5 average rating, 116 reviews

Bakery Next Door | Renovated | Golf Cart Avail.

Nectarine 13 is a centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

Top guest favorite

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.

Top guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 386 reviews

Pet friendly 3 bedroom beach house

Welcome to your perfect vacation getaway! This remodeled 3-bed, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. Bedrooms are equipped with comfy beds. Pet-Friendly: The spacious backyard and deck are perfect for playtime and relaxation. Great location close to shopping and restaurants. You’ll feel right at home in this safe neighborhood. Please note: No parties. Only 9 people are allowed at the house at any time

Superhost

Home in Chincoteague

4.9 out of 5 average rating, 113 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

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.