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570 Best cottages in Chesapeake Bay
8.8 3 reviews
Chesapeake Bay
08/23 – 08/28
$247/nighttotal: $1235 (5 )
Cottage On The Bay
2 2
cottage , Long Beach
This St. Leonard beach house offers proximity to three private beaches within walking distance or a short drive, and is 15 miles from Solomons Island and Prince Frederick. This family-friendly cottage accommodates four guests with two bedrooms and one bathroom, featuring a full kitchen, air conditioning, a jacuzzi, a garden, parking, and shared amenities like a fire pit and kayaks.
9.8 61 reviews
Chesapeake Bay
09/12 – 09/16
$228/nighttotal: $912 (4 )
Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay\n\n\n\n\n\n\n\n
2 2
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.
10 18 reviews
Chesapeake Bay
10/01 – 10/05
$237/nighttotal: $948 (4 )
Serenity Cottage: Central To State Parks, Historic Towns, Md & Va Beaches
2 3
cottage , New Church
Serenity Cottage, a two-bedroom vacation home near Pocomoke City, offers easy access to Pocomoke River State Park, Chincoteague Island, and Ocean City, Maryland. This octagon-shaped house sleeps five, features a fully equipped kitchen with unique vintage touches, a second-floor cupola room, and includes amenities such as air conditioning, internet, and parking.
9.8 202 reviews
Chesapeake Bay
07/20 – 07/27
$522/nighttotal: $3654 (7 )
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch
2 4
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.
This Tall Timbers vacation home boasts a riverfront location less than a mile from the Potomac River and within six miles of Piney Point Beach and Lighthouse. This 1,100-square-foot property features three bedrooms, one bathroom, a sofa bed, and sleeps eight, offering a fully equipped kitchen, free WiFi, a fireplace, a private garden, a spa, and access to an on-site arcade.
9.9 180 reviews
Chesapeake Bay
08/23 – 08/28
$408/nighttotal: $2040 (5 )
Cozy Cottage W/ Hot Tub, Pool Table, Fenced Yard
3 2
cottage , Norfolk
This Norfolk cottage is located just a short drive from popular beaches like Norfolk Beaches, Community Beach, and Ocean View Beach, making it an ideal spot for a coastal getaway. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience. The cottage has three bedrooms and can comfortably accommodate up to six guests, offering plenty of space for families or groups of friends. Enjoy amenities like a fully equipped kitchen, air conditioning, a private fenced yard with a barbecue grill, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
10 51 reviews
Chesapeake Bay
10/01 – 10/05
$286/nighttotal: $1144 (4 )
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.
2 3
cottage , Dunkirk
This charming cottage sits just a short walk from Fridays Creek Winery and a quick drive to the Patuxent River, offering a peaceful escape in a scenic location. It's rated excellent by previous guests, making it a popular choice for travelers seeking a relaxing stay. The 900 square foot cottage comfortably accommodates up to 4 guests with 2 bedrooms and 1 bathroom. Enjoy the amenities like a private pool, barbecue grills, and a spacious patio, perfect for relaxing and enjoying the beautiful surroundings.
9.8 315 reviews
Chesapeake Bay
08/23 – 08/28
$171/nighttotal: $855 (5 )
The Heron's Nest At Atlantic Marina
1 2
cottage , Lake Shore
This charming cottage is located in Pasadena, just steps from the beach on the Patapsco River, offering breathtaking water views and a peaceful escape. The cottage has consistently received excellent reviews from previous guests. The cottage has a spacious layout with 580 square feet of living space, one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a comfortable living area, a private porch, and access to a swimming pool, making it perfect for families and groups seeking a relaxing getaway.
10 167 reviews
Chesapeake Bay
07/20 – 07/27
$367/nighttotal: $2569 (7 )
Private 1300 Sq Ft Cottage In Historic Yorktown-w/ Trolley Access
1 4
cottage , Yorktown
This charming cottage is located in Yorktown's historic district, just a block from Main Street and two blocks from Yorktown Beach. Guests consistently rate the cottage as excellent, highlighting its unique privacy and prime location. The cottage offers 1300 square feet of private space, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen, private gardens, a terrace, and modern amenities like WiFi and air conditioning, making it perfect for a relaxing getaway.
8.0 4 reviews
Chesapeake Bay
06/20 – 06/27
$408/nighttotal: $2856 (7 )
Cozy Bay View Oceanside By Redawning
1 2
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.
10 4 reviews
Chesapeake Bay
08/23 – 08/28
$249/nighttotal: $1245 (5 )
Charming Cottage With Pool Access And Wifi In Lovely Rock Hall
1 2
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.
Chesapeake Bay
06/20 – 06/27
$364/nighttotal: $2548 (7 )
Sandy Mutts At The Beach By Redawning
1 2
cottage , Norfolk
This Norfolk beach house is located in East Ocean View, steps from the beach and within 6 miles of Ocean View Beach, Sarah Constant Shrine Beach, Little Creek Beach, and the Oceanview Fishing Pier. This two-bedroom, one-bathroom vacation rental sleeps four, features a full kitchen, laundry facilities, a patio, and on-site barbecue grills, perfect for enjoying the nearby attractions.
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.
Chesapeake Bay
07/20 – 07/27
$468/nighttotal: $3276 (7 )
Water Front Estate On Farm Cidery. Pet Friendly With Inviting Private Beach.
3 4
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.
10 74 reviews
Chesapeake Bay
09/12 – 09/16
$278/nighttotal: $1112 (4 )
Sandy Hill Sunsets
1 2
cottage , Nassawadox
This charming cottage is located in Exmore, right on the beach, near the Savage Neck Dunes Natural Area Preserve and Bethel Beach Natural Area Preserve. The cottage has received excellent user ratings, making it a popular choice for travelers seeking a peaceful and relaxing getaway. This one-bedroom, one-bathroom cottage offers 260 square feet of space and can comfortably accommodate up to 4 guests. The cottage features a fully equipped kitchenette, a private garden, air conditioning, parking, and internet access, ensuring a comfortable stay for all.
10 13 reviews
Chesapeake Bay
07/20 – 07/27
$322/nighttotal: $2254 (7 )
Rock Creek Cottage, Waterfront, Serene Views
2 4
cottage , Riviera Beach
This charming cottage is located in Riviera Beach, Pasadena, close to the Patapsco River and Chesapeake Bay, making it a great base for exploring the area. You’ll also be within easy reach of Baltimore, Annapolis, and Washington D.C. The cottage provides 990 square feet of space with 2 bedrooms and 2 bathrooms, accommodating up to 4 guests. You’ll enjoy access to a private deck and dock with water views, along with amenities such as a fully equipped kitchen, a spa, and a garden.
9.9 101 reviews
Chesapeake Bay
06/20 – 06/27
$358/nighttotal: $2506 (7 )
Cozy Getaway - Breezy Point Beach & Marina
1 2
cottage , Chesapeake Beach
This Chesapeake Beach cottage is a beachfront haven with a screened-in porch and pier access, offering a relaxing retreat just steps from Breezy Point Beach. With excellent user, location, and cleanliness ratings, this wheelchair-accessible cottage provides a comfortable and convenient stay for families and groups of up to six guests. The cottage features a 600-square-foot layout with two bedrooms, one bathroom, and a fully equipped kitchen. Guests can enjoy air conditioning, free Wi-Fi, and parking, as well as a garden and porch swing. The nearby attractions include jet skiing, waterparks, and a golf course.
Best Chesapeake Bay cottages with a garden
9.0 286 reviews
Chesapeake Bay
10/01 – 10/05
$271/nighttotal: $1084 (4 )
Norfolk Beach Cottage Rental
3 3
cottage , Norfolk
This family-friendly cottage is located just 3 miles from Norfolk Beaches and Ocean View Beach and within 6 miles of Nauticus and Little Creek Beach. It offers an excellent location for exploring the area's attractions and enjoying the beautiful coastline. The cottage has received excellent user ratings, making it a popular choice for travelers. This charming 3-bedroom vacation rental sleeps up to 6 guests and is perfect for families. The cottage offers a variety of amenities, including a private swimming pool, a barbecue grill, and a spacious garden, allowing you to relax and enjoy your stay.
9.6 47 reviews
Chesapeake Bay
08/23 – 08/28
$218/nighttotal: $1090 (5 )
Cozy Virginia Potomac Riverfront Cottage
4 2
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.
9.6 26 reviews
Chesapeake Bay
06/20 – 06/27
$364/nighttotal: $2548 (7 )
Waterfront River Cottage For 2, Dog-friendly
1 2
cottage , Severna Park
This charming beach house is just 9 miles from Severna Park, offering easy access to attractions like the B&A Trail, Severna Park Golf Center, and Bay Hills Golf Club. The property consistently receives excellent ratings for location, cleanliness, and overall user experience. The 560 square foot cottage comfortably accommodates two guests in one bedroom and one bathroom. Enjoy the private garden, relax on the balcony, or unwind in the arcade/game room, all while having access to a fully equipped kitchen, free WiFi, and a charcoal grill for outdoor dining.
10 51 reviews
Chesapeake Bay
07/20 – 07/27
$294/nighttotal: $2058 (7 )
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md.
1 4
cottage , Chesapeake Ranch Estates
This waterfront cottage is located in Fishing Creek, Chesapeake Ranch Estates, just 5.5 miles from Middle Hooper Island and within a 12-mile radius of Lower Hooper Island and Blackwater National Wildlife Refuge. The 700 square foot cottage features one bedroom, one bathroom, and can accommodate up to four guests, with amenities including a fully equipped kitchen, a private garden, and a terrace.
Frequently Asked Questions about cottages in Chesapeake Bay
When is the best time to rent a cottage in Baie de Chesapeake?
The shoulder seasons, spring and fall, are great for a cottage rental. You'll avoid the summer crowds and still enjoy pleasant weather. Plus, the fall foliage is spectacular.
What are the can't-miss sights in Baie de Chesapeake?
You can't miss the Chesapeake Bay Bridge, a stunning engineering feat connecting the Eastern Shore to the mainland. Also, the Chesapeake Bay Maritime Museum in St. Michaels is a great place to learn about the area's rich maritime history.
What are the best cottages with a pool in Chesapeake Bay?
Why consider renting a cottage in Baie de Chesapeake for your stay?
Cottages offer a unique way to experience the Bay, providing a peaceful and relaxing retreat. You'll be close to nature, enjoy privacy, and have access to amenities like private docks and fire pits.
What are the best cottages with a jacuzzi in Chesapeake Bay?
Can you easily explore Baie de Chesapeake on foot or by bike?
While some areas are walkable, exploring Chesapeake Bay is best done by car. You can find plenty of scenic drives and bike paths, but the distances between attractions are often too far to cover on foot.
What are the best cottages for families and kids in Chesapeake Bay?
What are the best restaurants in Baie de Chesapeake with nature views?
The Chart Room in St. Michaels offers delicious seafood and stunning waterfront views. On the Eastern Shore, you can also find great views at The Crab Claw in Cambridge or The Blackwater Grille in Cambridge.
What are the best pet friendly cottages in Chesapeake Bay?
What family-friendly activities are available in Baie de Chesapeake?
The Bay offers plenty of family-friendly activities, from exploring Assateague Island and its wild horses to visiting the National Aquarium in Baltimore or the Maryland Science Center. You can also enjoy a day of fishing, crabbing, or kayaking.
What are the best cottages with parking in Chesapeake Bay?
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.
10 3 reviews
Chesapeake Bay
09/12 – 09/16
$359/nighttotal: $1436 (4 )
Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach
1 2
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.
10 108 reviews
Chesapeake Bay
08/23 – 08/28
$293/nighttotal: $1465 (5 )
Firefly Cottage At The Cape, Community Beach, Spring Adventures, Hot Tub, Usna
1 2
cottage , Arnold
This charming cottage is located in the peaceful neighborhood of Cape Saint Claire, just 3.1 miles from Sandy Point State Park and within 6 miles of both Sandy Point Beach and Bay Hills Golf Club. Guests consistently rate this cottage as excellent, making it a popular choice for travelers seeking a comfortable and convenient stay. The cottage offers 660 square feet of space, accommodating up to 5 guests in a single bedroom and bathroom. Enjoy modern conveniences like air conditioning, a Jacuzzi, a terrace, a garden, and a spa, as well as a fully equipped kitchen and free Wi-Fi.
9.8 12 reviews
Chesapeake Bay
10/01 – 10/05
$519/nighttotal: $2076 (4 )
Waterfront Gloucester Cottage W/ Private Boat Dock
3 3
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.
9.8 16 reviews
Chesapeake Bay
08/23 – 08/28
$488/nighttotal: $2440 (5 )
Beachfront Hideaway - Pet Friendly, Hot Tub, Ev
2 2
cottage , Heathsville
This waterfront home in Lottsburg, Virginia, offers 100+ feet of private beach access (tide dependent) and is located about two hours from Washington, D.C., and a short drive from Reedville and Kilmarnock, placing you near the Compass entertainment center and several Virginia State Parks. This 1,100-square-foot vacation rental boasts two bedrooms, one bathroom, sleeps five, includes a fully equipped kitchen, a 7-person Marquis Crown Collection hot tub with a privacy wall, kayaks for exploring the Potomac River and Chesapeake Bay, blazing-fast broadband internet, and a ChargePoint Level 2 EV charger.
Browse Pet-Friendly Cottages in Chesapeake Bay
Traveling with a pet to Chesapeake Bay is simple at these cottages, featuring dog-friendly facilities.
9.6 5 reviews
Chesapeake Bay
08/23 – 08/28
$345/nighttotal: $1725 (5 )
Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly
1 2
cottage , Sanford
This waterfront cottage near the Eastern Shore of Virginia is conveniently located within 12 miles of the Virginia Welcome Center at New Church, Bloxom Winery, and the Wallops Flight Facility. This pet-friendly, one-bedroom, one-bathroom vacation rental sleeps two guests and boasts a fully equipped kitchen, private balcony, swimming pool, and access to outdoor grills; limited housekeeping is available.
10 16 reviews
Chesapeake Bay
09/12 – 09/16
$343/nighttotal: $1372 (4 )
Dog-friendly Westover Cottage W/ River Access!
2 2
cottage , Westover
This Westover cottage offers prime waterfront living on the Big Annemessex River, located 11 miles from the University of Maryland Eastern Shore and Janes Island State Park. This pet-friendly vacation home spans 1150 square feet, accommodating up to 7 guests in 2 bedrooms and a loft, and features direct river access with provided equipment for water activities.
9.6 131 reviews
Chesapeake Bay
10/01 – 10/05
$420/nighttotal: $1680 (4 )
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
2 3
cottage , Easton
This charming cottage is located in St. Michaels, just a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It has received excellent ratings from previous guests. The 1400 square foot home has two bedrooms and three bathrooms, comfortably accommodating up to five guests. Enjoy modern amenities like air conditioning, a swimming pool, a patio, a fireplace, and a fully equipped kitchen.
9.6 285 reviews
Chesapeake Bay
10/01 – 10/05
$459/nighttotal: $1836 (4 )
Premier St. Michaels Cottage - T. Blades House - Walk To Everything In Town
2 3
cottage , Easton
This charming cottage is located in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum and other popular attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The two-bedroom cottage provides 1400 square feet of space for up to five guests. Enjoy a relaxing stay with amenities like a private garden, a swimming pool, and a spa, as well as a fully equipped kitchen and modern conveniences like air conditioning and Wi-Fi.