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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.

Waterfront Cottage In Historic Charlestown, Maryland - Chesapeake Bay
10 11 reviews

Waterfront Cottage In Historic Charlestown, Maryland

cottage, Charlestown
This Charlestown cottage is located on Cattail Creek, just steps from the sandy beach at Footlog Park and a short drive from Havre de Grace.
The two-bedroom, one-bathroom cottage features a private dock, kayaks, and stunning waterviews from most areas, perfect for a relaxing getaway for up to four guests.
6 Block To Oceanfront And In The Center Of The Vibe District! - Chesapeake Bay
9.4 64 reviews

6 Block To Oceanfront And In The Center Of The Vibe District!

cottage, Virginia Beach
This Northeast Virginia Beach cottage is conveniently located less than a 10-minute walk from the Virginia Beach Convention Center and Boardwalk, and 3.1 miles from Sandbridge Beach.
This three-bedroom, one-bathroom vacation home sleeps seven, features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, a private patio, free Wi-Fi, and parking.
Secluded Waterfront Cottage On 200 Acre Farm Near Queenstown - Chesapeake Bay
10 111 reviews

Secluded Waterfront Cottage On 200 Acre Farm Near Queenstown

cottage, Queenstown
This waterfront cottage is situated within 9 miles of Queenstown's renowned attractions, including Queenstown Premium Outlets, Hazel Miner Monument, and Queenstown Harbor Golf Links. It is highly rated by previous guests for its excellent amenities and comfortable stay.
The cottage features three bedrooms and two bathrooms, accommodating up to eight guests. It offers a fully equipped kitchen, cozy fireplace, free WiFi, and a DVD player for entertainment. Guests can enjoy stunning waterfront views from the terrace or balcony, relax in the garden or spa, and utilize the barbecue grills for outdoor cooking.
Mid-century Rivah Retreat With Dock, Fire Pit & Cozy Fireplace - Chesapeake Bay
No reviews

Mid-century Rivah Retreat With Dock, Fire Pit & Cozy Fireplace

cottage, Saluda
This Gloucester waterfront cottage, near Thousand Trails Dog Park and Beach Park (within 3 miles) and 12 miles from Saluda's Main Street Center and Walter Reed Plaza, offers scenic views and easy access to local attractions.
This two-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen with a refrigerator, microwave, and oven, a terrace, and a garden; guests can enjoy on-site grilling and nearby water activities.

Best Chesapeake Bay cottages with a garden

Cozy Cottage With Access To And Partially Obstructed Views Of The Bay. - Chesapeake Bay
9.2 34 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.
Private Yard & Water Views: Cozy Urbanna Cottage - Chesapeake Bay
10 23 reviews

Private Yard & Water Views: Cozy Urbanna Cottage

cottage, Urbanna
This family-friendly cottage is located in Urbanna, just a short drive from the Middlesex County Museum and other attractions within a 20-mile radius. It's a great option for those looking for a peaceful getaway close to local history and entertainment. This highly rated vacation rental boasts an excellent user rating, making it a popular choice among travelers.
The cottage is spacious with 3 bedrooms, 2 bathrooms, and a floor area of 1500 square feet, comfortably accommodating up to 6 guests. The cottage includes a fully equipped kitchen, a cozy garden, and a patio for outdoor relaxation, as well as amenities like air conditioning, internet, and parking.
Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay - Chesapeake Bay
9.8 70 reviews

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay

cottage, Cecilton
This two-bedroom, one-bathroom cottage is located in Cecilton, just a short drive from the beach. It has an excellent user rating and can accommodate up to six guests. The cottage has a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking.
The cottage is also pet-friendly and family-friendly, and it has free WiFi. It is situated near the beach and has a garden with barbecue grills. The cottage is within 16 miles of Bohemia Vista Marina and Crow Farm and Vineyard, and within 20 miles of C and D Canal Museum and Back Creek Golf Club.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Chesapeake Bay
10 22 reviews

Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc

cottage, Long Beach
This Long Beach, St. Leonard's cottage offers easy beach access, a short walk from Flag Ponds Nature Park and Flag Harbor Marina, and less than 1.2 miles from Long Beach and Matoaka Beach.
This 800-square-foot vacation home sleeps five, boasting two bedrooms, two bathrooms, a full kitchen, a private patio, plus on-site amenities including a swimming pool, hot tub, and barbecue grills.

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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.

Waterfront Cottage@chesapeakeparadise Hot Tub/dogs - Chesapeake Bay
9.7 289 reviews

Waterfront Cottage@chesapeakeparadise Hot Tub/dogs

apartment, Deale
This charming cottage sits on the western shore of the Chesapeake Bay, just a short drive from Washington, D.C., Annapolis, and Baltimore, offering a serene escape from the city. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The vacation home features three bedrooms and two bathrooms, spanning 1190 square feet and comfortably accommodating up to eight guests. The cottage boasts a private pier, a fenced-in yard, a swimming pool, kayaks, a canoe, a fire pit, swings, and a BBQ grill, ensuring a fun-filled and relaxing stay.
Smith Beach Cottage W/ Private Sunset - Chesapeake Bay
9.6 15 reviews

Smith Beach Cottage W/ Private Sunset

cottage, Eastville
This Eastville cottage offers private beach access and is located near the Chesapeake Bay and Cape Charles Beach.
This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features a private hot tub, air conditioning, and internet.
Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
9.6 14 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.
Hays Beach House - Hot Tub - Private Beach - Chesapeake Bay
9.6 17 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.

Browse Pet-Friendly Cottages in Chesapeake Bay

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

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Chesapeake Bay
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland coastal cottage, a short drive from Annapolis and easily accessible to Kent Island wedding venues, offers convenient proximity to Queenstown Harbor Golf Links and Paul Reed Smith Guitars.
This 1190-square-foot vacation home features two bedrooms, two bathrooms, and accommodates six guests, boasting a screened porch with fireplace, a private barrel sauna, and outdoor amenities including a BBQ grill and firepit.
Cozy Beach Cottage - Walking Distance To The Beach!! - Chesapeake Bay
9.8 95 reviews

Cozy Beach Cottage - Walking Distance To The Beach!!

cottage, Virginia Beach
This charming 3-bedroom cottage is conveniently located in Northeast Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina. Guests consistently rate this vacation rental "excellent" for its comfortable accommodations and convenient location.
The 1600 square foot cottage comfortably sleeps six guests and features a fully equipped kitchen, a private yard, and a barbecue grill. Enjoy the Virginia Beach sunshine and fresh air with access to the beach, nearby parks, and local attractions.
Quarry Landing - Center Of Town & River View - 3 Bedroom - Chesapeake Bay
10 14 reviews

Quarry Landing - Center Of Town & River View - 3 Bedroom

cottage, Port Deposit
This Port Deposit vacation home is located 0.4 miles from the Susquehanna River, within 6 miles of Hollywood Casino and Garrett Island Beach, and under 9 miles from Perry Point VA Medical Center and Conowingo Dam.
This three-bedroom, one-bathroom house sleeps nine guests and features a fully equipped kitchen, a swimming pool, a terrace, free Wi-Fi, and a Smart TV; an on-site water park provides additional recreation.
Private Beach Front Getaway At The Sunshine Beach Cottage. - Chesapeake Bay
9.8 85 reviews

Private Beach Front Getaway At The Sunshine Beach Cottage.

cottage, Piney Point
This Piney Point cottage is a short drive from Point Lookout State Park, Elms Beach Park, and Confederate Memorial Park, offering easy access to the area's natural beauty and historical sites. It has received excellent user ratings, indicating a comfortable and enjoyable stay for guests.
The two-bedroom cottage spans 980 square feet and comfortably accommodates up to eight guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a terrace, a garden, and free Wi-Fi, perfect for relaxing and enjoying the beautiful surroundings.
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