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570 Best cottages in Chesapeake Bay
8.0 30 reviews
Chesapeake Bay
07/30 – 08/05
$537/nighttotal: $3222 (6 )
Sandy Dunes Beachfront Cottage - Beach Front
3 6
cottage , Norfolk
This Norfolk beach house is located just a short walk from the sand and surf, offering easy access to the area's beautiful beaches and attractions. It's rated very good for location, cleanliness, and overall experience. The three-bedroom cottage has a spacious 1850 square feet of living space. Enjoy features like a fully equipped kitchen, a private fenced yard, a playground for kids, and outdoor grills, all while staying connected with free WiFi.
9.9 68 reviews
Chesapeake Bay
08/23 – 08/28
$727/nighttotal: $3635 (5 )
Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger
3 2
cottage , Piney Point
This charming cottage sits on the Chesapeake Bay in Piney Point, offering a private beach and fishing pier, just a short walk from a semi-public beach and close to local attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The cottage has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a relaxing stay with amenities like a fully equipped kitchen, air conditioning, a terrace, and a garden, as well as access to water activities such as kayaking, paddleboarding, and fishing.
10 6 reviews
Chesapeake Bay
08/29 – 09/05
$208/nighttotal: $1456 (7 )
The Cottage At Merryland Farm
1 2
cottage , Kingsville
This 800-square-foot cottage rental near Hydes, Baltimore County, provides easy access to Oregon Ridge Nature Center, Ladew Topiary Gardens, and wineries. The one-bedroom, one-bathroom house sleeps three, features a full kitchen with a refrigerator and microwave, air conditioning, and a private garden; well-behaved dogs are allowed with prior approval.
9.6 26 reviews
Chesapeake Bay
07/30 – 08/05
$620/nighttotal: $3720 (6 )
Adorable Chesapeake Bay Beach Cottage A Just 1 Block From The Sand!
3 6
cottage , Virginia Beach
This family-friendly cottage is located in Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina, with Chesapeake Beach and Sylvan Beach within a three-mile radius. The cottage has received excellent reviews from previous guests. This 3-bedroom, 3-bathroom vacation rental comfortably accommodates 6 guests and offers 1800 square feet of living space. The cottage features a fully-equipped kitchen, a private pool, a spa, a terrace, a garden, and free parking.
10 4 reviews
Chesapeake Bay
08/29 – 09/05
$223/nighttotal: $1561 (7 )
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.
10 11 reviews
Chesapeake Bay
07/20 – 07/27
$295/nighttotal: $2065 (7 )
Oyster Cottage - Walk To Shops , Mainstay Music Venue And The Bay!
2 4
cottage , Rock Hall
Oyster Cottage is located in Rock Hall, just a short walk from the waterfront, shops, restaurants, and entertainment. The cottage has received excellent user ratings and is a great option for families and pet owners. The cottage features two bedrooms, one bathroom, and can accommodate up to seven guests. The cottage offers a well-equipped kitchen, a spacious living area, a relaxing jacuzzi, and a private outdoor space with a patio, a grill, and a garden.
9.9 126 reviews
Chesapeake Bay
07/20 – 07/27
$479/nighttotal: $3353 (7 )
The Little Blue Cottage - Topping : Waterfront!
3 4
cottage , White Stone
This waterfront cottage in White Stone offers stunning views of the bay and creek, a short walk from the marina and a short drive from acclaimed restaurants. It has consistently received excellent ratings for user experience, location, and cleanliness. The three-bedroom, two-bathroom cottage spans 1360 square feet and comfortably accommodates up to six guests. Enjoy modern amenities, a private dock with kayaks, and multiple dining areas, perfect for relaxing and enjoying the peaceful atmosphere.
9.0 8 reviews
Chesapeake Bay
08/23 – 08/28
$235/nighttotal: $1175 (5 )
Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.
1 2
cottage , Benedict
This Benedict, Maryland beach house boasts a unique beachfront location with over 500 feet of private beach and a 400-foot pier, near the Dr. Samuel A. Mudd House Museum and Drum Point Lighthouse. This one-bedroom, one-bathroom vacation rental sleeps six, featuring a queen bed, bunk beds, a sleeper sofa, a full kitchen with a fridge and microwave, air conditioning, a terrace, a garden, a spa, and a gas grill; enjoy nearby Walter's Walk sandbar for sunset viewing.
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.
10 32 reviews
Chesapeake Bay
07/20 – 07/27
$295/nighttotal: $2065 (7 )
Beach Cottage By The Sea....
2 4
cottage , Kilmarnock
This beachfront cottage in Reedville is within 15 km of the Reedville Fishermen's Museum, Smith Point Marina, and Buzzard's Point Marina. It has excellent user ratings and can accommodate up to 6 guests in 2 bedrooms and 2 bathrooms. The cottage features a private garden with barbecue grills for outdoor relaxation and entertainment, a fully equipped kitchen with essential appliances for self-catering, air conditioning, a terrace or balcony, parking, and free WiFi. It is also pet-friendly and family-friendly.
Chesapeake Bay
07/20 – 07/27
$276/nighttotal: $1932 (7 )
Potomac River Cottage - Waterfront Cottage With Endless Views!
2 4
cottage , Heathsville
This 2-bedroom, 1-bathroom cottage in Ophelia offers 4 guests expansive Potomac River waterfront views and is located near Bush Mill Stream Natural Area Preserve and Ginny Beach. This riverside retreat features a large deck for observing passing ships and provides easy access to cultural attractions like the Northern Neck Farm Museum and Reedville Fishermen's Museum, with internet, air conditioning, and parking available.
9.6 4 reviews
Chesapeake Bay
08/23 – 08/28
$178/nighttotal: $890 (5 )
Near Chincoteague & Assateague Island\ncharming 2-bedroom Cottage
2 2
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.
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.
9.7 275 reviews
Chesapeake Bay
10/01 – 10/05
$412/nighttotal: $1648 (4 )
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok
3 3
cottage , 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.
8.6 39 reviews
Chesapeake Bay
07/30 – 08/05
$519/nighttotal: $3114 (6 )
Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed
3 6
cottage , Norfolk
This Willoughby Spit cottage is located directly on the beach, just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. The cottage has received a very good user rating, making it a popular choice for travelers. This 3-bedroom home comfortably sleeps up to 8 guests and features a fully equipped kitchen, a fireplace, and a patio. Enjoy the convenience of on-site amenities like a playground, barbecue grills, and free WiFi, along with easy access to the nearby Oceanview Fishing Pier.
10 79 reviews
Chesapeake Bay
07/30 – 08/05
$197/nighttotal: $1182 (6 )
Idle Hour, A Tranquil 3 Bedroom 1.5 Bath Cottage With Dock & Golf Cart Rental
3 6
cottage , Smith Island
This waterfront cottage on Terrapin Sand Point is only 0.1 miles from the point and 2.5 miles from Smith Island. It is highly rated for its location, cleanliness, and user experience. The cottage has 3 bedrooms and can accommodate up to 6 guests. It features a kitchen with a refrigerator, oven, stovetop, and microwave, as well as free WiFi, air conditioning, and a terrace or balcony. Guests can also enjoy the barbecue grills and garden.
10 370 reviews
Chesapeake Bay
08/29 – 09/05
$229/nighttotal: $1603 (7 )
Cottage On A Private Island In The York River
3 2
cottage , Gloucester Point
This waterfront cottage in Gloucester Point is conveniently located within 9 miles of popular attractions like Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, making it a great base for exploring the area. The property has earned excellent user ratings, suggesting a high level of satisfaction among previous guests. The 1500 square foot cottage comfortably sleeps up to 8 guests in its 3 bedrooms. Enjoy amenities like a private pool, a spa, a terrace, and a fully equipped kitchen, along with access to a garden, a barbecue grill, and a water park.
Best Chesapeake Bay cottages with a garden
9.2 7 reviews
Chesapeake Bay
10/01 – 10/05
$183/nighttotal: $732 (4 )
Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills
2 3
cottage , Queenstown
This Queenstown, Maryland cottage is conveniently located near the Avalon Theatre and The Third Haven Friends Meeting House, offering easy access to area attractions like the Hazel Miner Monument and Adkins Arboretum. This two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen (fridge, microwave), air conditioning, Wi-Fi, a terrace, garden, parking, and a washer/dryer; pets are welcome.
9.8 315 reviews
Chesapeake Bay
07/20 – 07/27
$380/nighttotal: $2660 (7 )
The Heron's Nest At Atlantic Marina
1 4
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 21 reviews
Chesapeake Bay
07/30 – 08/05
$343/nighttotal: $2058 (6 )
Private Yard & Water Views: Cozy Urbanna Cottage
3 6
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.
9.8 61 reviews
Chesapeake Bay
08/29 – 09/05
$225/nighttotal: $1575 (7 )
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.
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
08/29 – 09/05
$323/nighttotal: $2261 (7 )
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.
10 4 reviews
Chesapeake Bay
08/23 – 08/28
$339/nighttotal: $1695 (5 )
Smith Beach Cottage W/ Private Sunset
2 2
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.
10 1 review
Chesapeake Bay
10/01 – 10/05
$761/nighttotal: $3044 (4 )
Cozy Cottage
4 3
cottage , Dundalk
This Dundalk cottage rental is conveniently located within 6 miles of Johns Hopkins Bayview Medical Center, the Baltimore Cruise Terminal, and Johns Hopkins Hospital, offering easy access to medical facilities and cruise departures. This four-bedroom, two-bathroom vacation home sleeps eight guests and boasts a fully equipped kitchen, in-unit laundry, a Jacuzzi, and a private garden with parking; nearby attractions include the Inner Harbor and Fort McHenry.
Browse Pet-Friendly Cottages in Chesapeake Bay
Traveling with a pet to Chesapeake Bay is simple at these cottages, featuring dog-friendly facilities.
8.6 16 reviews
Chesapeake Bay
07/30 – 08/05
$522/nighttotal: $3132 (6 )
Manor And Mutts #1 - Beach Front, Pet Friendly, High Speed Wifi, Private
4 6
cottage , Norfolk
This charming beach house in Willoughby Spit is located just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. It's a great option for travelers looking for a relaxing getaway close to the beach and local attractions. Guests have rated this cottage "very good" for its comfortable accommodations and convenient location. This 4-bedroom home comfortably sleeps 8 guests, providing plenty of space for families or groups of friends. The cottage features a fully equipped kitchen, a fireplace, a private fenced yard, and a terrace or balcony, making it perfect for enjoying the beautiful Norfolk weather.
10 4 reviews
Chesapeake Bay
10/01 – 10/05
$266/nighttotal: $1064 (4 )
"Dragonfly" Waterfront Cottage On Chesapeake Bay
3 3
cottage , Kilmarnock
This Chesapeake Bayfront cottage rental in Reedville, a short drive from Kilmarnock, offers direct bay frontage with a private cove perfect for swimming, kayaking, and fishing, and is near attractions like the Reedville Fishermen's Museum and Compass Entertainment Complex. The one-bedroom, one-bathroom house sleeps four with a queen bed and fold-out couch, features a small kitchen, air conditioning, Wi-Fi, a garden, and access to 30 acres of waterfront property including two outdoor soaking tubs and water toys.
10 65 reviews
Chesapeake Bay
08/29 – 09/05
$317/nighttotal: $2219 (7 )
Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries.
3 2
cottage , Heathsville
This waterfront Heathsville cottage, located in Lottsburg, offers easy access to the Chesapeake Bay Wine Trail, Bush Mill Stream Natural Area Preserve, and Sandy Point Beach, with nearby marinas, breweries, antique shops, and wineries. The three-bedroom, two-bathroom home sleeps nine guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, a tennis court, and on-site parking, plus excellent internet access.
9.6 20 reviews
Chesapeake Bay
07/30 – 08/05
$678/nighttotal: $4068 (6 )
Secluded Cozy Cottage In Historic Downtown
2 6
cottage , Annapolis
This charming cottage, in the Historic District of Annapolis, offers immediate access to the city's iconic landmarks and attractions. The restored 1930s cottage has an open and airy interior with vaulted ceilings and an open floor plan. The cottage has 2 bedrooms, 1 bathroom, and can accommodate up to 8 guests. It features a fully equipped gourmet kitchen, a comfortable living area with a large couch, chaise lounge chairs, a 55" Roku TV, and an electric fireplace. The cottage also has a private entrance and patio, and is pet-friendly.