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Chesapeake Bay cottages
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546 Best cottages in Chesapeake Bay

Best Family-Friendly Cottages in Chesapeake Bay

Family vacations in a cottage near the water in Chesapeake Bay thrive with extra space, and room for the whole family to relax.

Near Chincoteague & Assateague Island Charming 2-bedroom Cottage - Chesapeake Bay
9.8 9 reviews

Near Chincoteague & Assateague Island Charming 2-bedroom Cottage

cottage, Saxis
This Saxis, Virginia cottage is conveniently located near Bloxom Winery and Somers Cove Marina, offering easy access to the Chesapeake Forest – Dunn Swamp Complex and Kegotank Bay.
The two-bedroom, one-bathroom home sleeps four guests comfortably, featuring a queen and a full bed, WiFi, a washer, and a fully equipped kitchen with a refrigerator and microwave; nearby activities include wine tasting and birdwatching.
Unique Tangier Cottage W/ Chesapeake Bay Views! - Chesapeake Bay
10 17 reviews

Unique Tangier Cottage W/ Chesapeake Bay Views!

cottage, Tangier
This Tangier family-friendly vacation home is conveniently located within a 10-minute walk of both the Tangier History Museum and Tangier Island Beach.
The 1800-square-foot house features four bedrooms, two bathrooms, sleeps eight guests, and includes amenities such as a fully equipped kitchen, air conditioning, a terrace, a garden, free parking, and Wi-Fi.
Esva Down By The Sea & Pet Friendly - Chesapeake Bay
9.8 7 reviews

Esva Down By The Sea & Pet Friendly

cottage, Savageville
This seaside cottage rental in Onancock, Virginia, offers easy access to the Onancock Wharf, Kegotank Bay, and is a short drive from Chincoteague Island (30 minutes) and Cape Charles (40 minutes).
This 1000-square-foot vacation home features two bedrooms, one bathroom, accommodates four guests, and includes amenities such as air conditioning, a full kitchen (fridge, microwave), Wi-Fi, and a private garden with parking.
Cozy Virginia Potomac Riverfront Cottage - Chesapeake Bay
9.6 50 reviews

Cozy Virginia Potomac Riverfront Cottage

cottage, Montross
This waterfront cottage rental in Hague, Northern Neck, Virginia, offers easy access to nearby wineries like Hague Winery and Vault Field Vineyards, as well as historical sites such as the Kinsale Museum and Piney Point Lighthouse.
The two-bedroom, two-bathroom house sleeps seven, features a fully equipped kitchen with a dishwasher, a 50-foot private dock perfect for fishing and crabbing, and includes free Wi-Fi and air conditioning.

Best Chesapeake Bay cottages with a garden

Mermaid's And Mutts Retreat - Beach Front, Pet Friendly, Wi-fi, Off-street Park - Chesapeake Bay
9.0 34 reviews

Mermaid's And Mutts Retreat - Beach Front, Pet Friendly, Wi-fi, Off-street Park

cottage, Norfolk
This Norfolk beach house is located less than a mile from Norfolk Beaches and Community Beach, and within three miles of Ocean View Beach and Sarah Constant Shrine Beach, offering easy access to the area's beautiful coastline. The property has received excellent user ratings, making it a popular choice for travelers.
This three-bedroom vacation rental can accommodate up to eight guests, providing ample space for families or groups of friends. The house includes a fully equipped kitchen, a terrace with beach views, a garden, and parking, as well as amenities like internet, air conditioning, and a dishwasher.
Waterfront Cottage On Candy Point:  Family-friendly And Dog-friendly! - Chesapeake Bay
9.6 129 reviews

Waterfront Cottage On Candy Point: Family-friendly And Dog-friendly!

cottage, Heathsville
Located in Heathsville, this cottage is within 12 miles of historical sites such as Reedville Fishermen's Museum and offers an excellent user rating.
This two-bedroom, one-bathroom cottage features a patio and free WiFi. It has a kitchen with a refrigerator and oven, as well as a fireplace for cozy evenings. Guests can enjoy the onsite playground and barbecue grills, and explore the nearby Heathsville Farmers' Market.
Charming Cottage With Pool Access And Wifi In Lovely Rock Hall - Chesapeake Bay
10 4 reviews

Charming Cottage With Pool Access And Wifi In Lovely Rock Hall

cottage, Rock Hall
This Rock Hall cottage, centrally located and within walking distance of Rock Hall Harbor, the Waterman's Museum, and The Mainstay, offers easy access to local attractions.
The 600-square-foot, two-story house features one bedroom with a king-size bed, one bathroom, and accommodates two guests; amenities include a private pool (May 1st–September 21st, 11 am–5 pm access), air conditioning, Wi-Fi, and on-site parking.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland - Chesapeake Bay
9.6 17 reviews

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland

cottage, Piney Point
This Piney Point waterfront cottage, located in Point Lookout, Southern Maryland, offers stunning Chesapeake Bay views and is minutes from Point Lookout State Park and the Smith Island Ferry.
The 1020-square-foot home features two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, high-speed Wi-Fi, air conditioning, a private dock, fire pit, and Adirondack chairs.

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Guest-Favorite Cottages with Jacuzzi in Chesapeake Bay

These cottages in Chesapeake Bay feature private hot tubs and jacuzzis, perfect for a relaxing soak after a day by the water.

Hays Beach House - Hot Tub - Private Beach - Chesapeake Bay
9.8 16 reviews

Hays Beach House - Hot Tub - Private Beach

cottage, Piney Point
Hays Beach House is a waterfront cottage situated in the Point Lookout neighborhood of Scotland, Maryland, near Historic St. Mary's City and Patuxent River Naval Air Museum. It has an excellent user rating.
The cottage has 5 bedrooms and 5 bathrooms, and can accommodate up to 12 guests. It features a private beach with crabbing, fishing, kayaking, and stand-up paddleboarding opportunities, a hot tub on the screened porch with sunset views, a private deck overlooking the bay, a gourmet kitchen, a balcony on the top floor with panoramic Chesapeake Bay vistas, and is pet-friendly.
Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
9.8 12 reviews

Waterfront Gloucester Cottage W/ Private Boat Dock

cottage, Gloucester Point
This Gloucester Point vacation home sits 1.2 miles from Rosewell Ruins and 1.3 miles from Middle Peninsula State Park, offering easy access to White Marsh Shopping Center and Catlett Islands within a 9-mile radius.
This 1500-square-foot seaside rental boasts four bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, Jacuzzi, private patio, and parking.
Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach

cottage, Cheriton
This Cape Charles cottage, located near Brockenberry Bay and eight miles from the Cape Charles Historic District and beaches, offers easy access to Kiptopeke State Park (12 miles) and Bay Creek Resort & Golf Club (9 miles).
This 400-square-foot vacation home sleeps four with two bedrooms, one bathroom, a full kitchen including a dishwasher, a Jacuzzi, and a private terrace, plus a spacious yard with a fire pit and hammocks.
3 Br Bay Home W Private Dock & All The Amenities - Chesapeake Bay
10 25 reviews

3 Br Bay Home W Private Dock & All The Amenities

cottage, Mathews
This Mathews County waterfront home in Onemo, Virginia, offers stunning views and is 2.8 miles from Bethel Beach Natural Area Preserve and 32 miles from the Deltaville Maritime Museum and Steamboat Era Museum.
The four-bedroom, two-bathroom vacation rental sleeps eight, features a fully equipped kitchen, jacuzzi, and a terrace, plus on-site amenities including a hot tub, arcade/game room, and barbecue grills.

Browse Pet-Friendly Cottages in Chesapeake Bay

Traveling with a pet to Chesapeake Bay is simple at these cottages, featuring dog-friendly facilities.

Cozy Cottage With Access To And Partially Obstructed Views Of The Bay. - Chesapeake Bay
9.2 33 reviews

Cozy Cottage With Access To And Partially Obstructed Views Of The Bay.

cottage, Calvert Beach
This charming cottage is located in Port Republic, a peaceful rural area near the beach and a short drive from Calvert Cliffs. It has received excellent ratings from previous guests.
The cottage has three bedrooms and two bathrooms and can accommodate up to ten guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a garden, and parking. Guests can enjoy tranquil surroundings, unique views, beach access, and proximity to local attractions, making it an ideal choice for families and groups seeking a relaxing getaway.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Chesapeake Bay
9.8 206 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton
This charming cottage is located in the picturesque town of St. Michaels, just a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. Guests have consistently rated this property excellent for its comfort and convenience.
The cottage offers 1,400 square feet of space, with two bedrooms and two bathrooms, accommodating up to five guests. Enjoy a fully equipped kitchen, a private patio, a garden, and a swimming pool, along with other amenities like air conditioning, a washer and dryer, and free parking.
Water Front Estate On Farm Cidery.  Pet Friendly With Inviting Private Beach. - Chesapeake Bay
10 1 review

Water Front Estate On Farm Cidery. Pet Friendly With Inviting Private Beach.

cottage, Kilmarnock
This pet-friendly waterfront cottage in Kilmarnock is situated on 100 ft of shoreline, offering a private retreat near the Steamboat Era Museum and the Mary Ball Washington Museum and Library, with Good Luck Cellars and the Compass Entertainment Complex also within convenient reach.
This 1440 sq ft dwelling accommodates up to 6 guests, featuring 4 bedrooms and 2 bathrooms, and includes amenities such as a microwave, dishwasher, air conditioning, a terrace, garden, and parking, with complimentary stand-up paddleboards available for exploring the water.
Cozy Bay View Oceanside By Redawning - Chesapeake Bay
No reviews

Cozy Bay View Oceanside By Redawning

cottage, Norfolk
This Norfolk, Virginia cottage is situated in the desirable Willoughby Spit district, within two miles of Norfolk beaches, Sarah Constant Shrine Beach, and the Oceanview Fishing Pier.
This one-bedroom, one-bathroom vacation home sleeps three guests and features a fully equipped kitchen with a refrigerator and microwave, air conditioning, parking, Wi-Fi, and an outdoor barbecue grill.
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