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Price per night
Accommodation type
Rating
481 Unique places to stay in Chesapeake Bay
Chesapeake Bay
08/23 – 08/28
$183/nighttotal: $915 (5 )
Woodsy + Secluded! Amish Country Retreat In Hartly
1 2
apartment , Hartly
This apartment in Hartly, Kent County, is located near local Amish markets and within 17 miles of Blackbird State Forest and Bombay Hook National Wildlife Refuge. This 320 sq ft studio dwelling accommodates two guests and features a kitchenette with a fridge and microwave, air conditioning, parking, and a front porch, with the option for dog-friendly stays for an additional fee.
Chesapeake Bay
07/20 – 07/27
$3038/nighttotal: $21266 (7 )
Luxurious 50 Ft. Fountaine Pajot Saba. Six Cabin Six Head Layout.
6 4
houseboat , Riva
This luxurious houseboat in Edgewater, Maryland, offers unique Chesapeake Bay views and is conveniently located within three miles of Annapolis, the Annapolis Harbor Center Shopping Center, the Kunta Kinte-Alex Haley Memorial, and Anne Arundel Medical Center. This six-bedroom, six-bathroom vessel sleeps twelve guests and features a kitchen, air conditioning, on-site paddleboards, and is a smoke-free environment, making it ideal for exploring Annapolis and the surrounding area.
10 53 reviews
Chesapeake Bay
10/01 – 10/05
$234/nighttotal: $936 (4 )
Charming Waterfront Farmhouse 10 Minutes From Blackwater Nwr - Pet Friendly
2 3
farm , Chesapeake Ranch Estates
This waterfront gîte is located in Fishing Creek, just 5.5 miles from Middle Hooper Island. It has been awarded an excellent user rating and is a popular choice for families visiting Chesapeake Ranch Estates. The gîte has a floor area of 1250 square feet and can accommodate up to 6 guests in its 2 bedrooms and 1 bathroom. It features a fully equipped kitchen, a living room, and a bathroom. Guests can also enjoy the garden, terrace, and barbecue grills. The gîte is also pet-friendly and offers amenities such as air conditioning, internet, and parking.
10 9 reviews
Chesapeake Bay
10/01 – 10/05
$458/nighttotal: $1832 (4 )
Pizza Friday
4 3
cabin , Piney Point
This Piney Point waterfront cottage is located less than a mile from Cardinal Gibbons Park and First District Community Park, and approximately three miles from Saint Inigoes State Forest, offering easy access to outdoor recreation. Sleeping up to ten guests, this four-bedroom, two-bathroom home features a fully equipped kitchen, free WiFi, a fireplace, a terrace, a garden, barbecue grills, and a smart TV, perfect for family vacations.
9.4 19 reviews
Chesapeake Bay
10/01 – 10/05
$229/nighttotal: $916 (4 )
Private 3br Farmhouse On Estate With Event Space, Horses,trails, Ponds & Orchard
3 3
farm , Smyrna
This Townsend, Delaware farm stay, near Smyrna, offers easy access to Old Bohemia Wildlife Management Area and Fort DuPont State Park. This 1,292-square-foot rural estate boasts three bedrooms, two bathrooms, sleeps eight, and includes a full kitchen, hot tub, and access to horse trails, fishing ponds, and an apple orchard.
9.9 335 reviews
Chesapeake Bay
09/12 – 09/16
$147/nighttotal: $588 (4 )
"The Little Red Cabin" Aka The Galley
1 2
cabin , Deltaville
This Deltaville cabin is located right on the water in a campground, offering views of the Bay and beach. The cabin has received excellent ratings for location, cleanliness, and overall experience. The cozy cottage features a kitchen, bedroom, bathroom, family room with a fireplace, and a dining area. Guests can enjoy the campground amenities, including a pier, beach, kayaks, and a canoe, and can relax on the large screened-in porch.
9.8 57 reviews
Chesapeake Bay
09/12 – 09/16
$312/nighttotal: $1248 (4 )
Chesapeake Houseboat Getaway On Kent Island, Maryland
2 2
houseboat , Stevensville
This Stevensville houseboat is situated on the Chesapeake Bay, just a short drive from Annapolis, Chestertown, Easton, St. Michaels, and Oxford. It’s located in a peaceful marina with easy access to the beach and wildlife. The houseboat has an excellent user rating and is perfect for families or groups of up to six people. The 1,000-square-foot houseboat has two bedrooms, one bathroom, a fully equipped kitchen, a garden, and parking. It also includes air conditioning, internet, and a floating dock that provides easy access regardless of the tide. Guests can enjoy waterfront views, kayaking, motor boating, cycling, hiking, and easy access to local attractions.
9.9 108 reviews
Chesapeake Bay
10/01 – 10/05
$377/nighttotal: $1508 (4 )
Cabin On The Creek ~ Kayaks And Fire Pit
1 3
cabin , Butlertown
This waterfront cabin in Butlertown offers a unique and serene retreat on a bluff overlooking Churn Creek. It has received excellent ratings for its location, cleanliness, and amenities. The cabin has 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a modern and stylish interior, a spacious kitchen, comfortable bedrooms, and luxurious bathrooms. Guests can enjoy direct access to a private dock for swimming, kayaking, and fishing, as well as a fire pit for cozy evenings under the stars.
10 9 reviews
Chesapeake Bay
10/01 – 10/05
$311/nighttotal: $1244 (4 )
Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields
4 3
farm , West Point
This Buena Vista farmhouse rental in Middlesex County sits between West Point and Gloucester, providing easy access to the Middlesex County Museum and Gloucester Museum of History. This 3000-square-foot property boasts four bedrooms, three bathrooms, and accommodates up to ten guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a terrace, air conditioning, and a lovely garden.
9.7 275 reviews
Chesapeake Bay
09/12 – 09/16
$237/nighttotal: $948 (4 )
Waterfront Solomons Island Art Cottage
1 2
bungalow , Solomons
This waterfront cottage sits on Solomons Island, Maryland, a short walk from Solomons' restaurants and bars. The one-bedroom, one-bathroom house sleeps two, features a full kitchen with dishwasher and microwave, laundry facilities, kayaks for exploring Back Creek and the Patuxent River, and offers stunning sunset views over the Patuxent River.
10 2 reviews
Chesapeake Bay
10/01 – 10/05
$499/nighttotal: $1996 (4 )
Relax In Style At This Airy 3br/2ba Retreat With Outdoor Oasis
3 3
farm , Grasonville
This Grasonville farm stay is conveniently located near Queenstown Premium Outlets (a 12-minute drive) and Queenstown Harbor Golf Links (a 16-minute drive). This 2200-square-foot property features three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, laundry facilities, air conditioning, a fireplace, a BBQ, and on-site parking.
8.6 17 reviews
Chesapeake Bay
10/01 – 10/05
$457/nighttotal: $1828 (4 )
Fisherman's Cabin - Water Front And Pet Friendly By Redawning
3 3
cabin , Norfolk
This Norfolk cabin is located in Willoughby Spit, just a short drive from Norfolk Beaches and other popular attractions. The cabin has a user rating of very good and is rated OK for location and cleanliness. This 3-bedroom, 1-bathroom cabin offers 1450 square feet of space. It features a kitchen with a fridge, freezer, and microwave, a terrace, a garden, parking, air conditioning, Wi-Fi, a washing machine, and barbecue grills.
Top Family Unique Stays in Chesapeake Bay
Kid-friendly unique stays in Chesapeake Bay offer a perfect blend of excitement and convenience for a happy family getaway.
9.6 34 reviews
Chesapeake Bay
10/01 – 10/05
$305/nighttotal: $1220 (4 )
Fully Equipped Docked Houseboat At Log Pond Marina In Havre De Grace, Md.
4 3
houseboat , Havre de Grace
This houseboat is docked at Log Pond Marina in Havre de Grace, Maryland, a charming bay town close to Annapolis, Baltimore, Washington DC and Philadelphia. It has received excellent user ratings and allows pets. This spacious floating home has four bedrooms and two bathrooms, comfortably accommodating up to eight guests. It features a party deck, modern amenities like air conditioning and a washer/dryer, and easy access to local attractions and marina amenities.
10 6 reviews
Chesapeake Bay
06/20 – 06/27
$763/nighttotal: $5341 (7 )
6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino
6 13
farm , Perryville
This farm stay is located in Perryville, just a short drive from the Susquehanna Museum at the Lock House and Concord Point Lighthouse, offering easy access to historical attractions and the natural beauty of the surrounding area. This spacious property provides comfortable accommodations for up to 16 guests with 6 bedrooms and 4 bathrooms, encompassing a generous 3050 square feet of living space. This rural retreat offers a variety of amenities, including a fully equipped kitchen, a fitness center, a garden, and multiple entrances for convenient access, making it an ideal destination for families and groups seeking a relaxing getaway.
Chesapeake Bay
08/23 – 08/28
$371/nighttotal: $1855 (5 )
Rustic 3br Waterfront Cabin With Firepit + Dock Access
3 2
cabin , Montross
This waterfront cottage in Hague offers direct Potomac River access and is a 5-minute walk to Coles Point Tavern, with Stratford Hall a 20-minute drive away. This 1190 sq ft lodge accommodates up to 7 guests with 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, complimentary kayaks and bikes, a screened porch with river views, and an outdoor fire pit.
10 2 reviews
Chesapeake Bay
08/23 – 08/28
$366/nighttotal: $1830 (5 )
Blue Heron Farm Waterfront Chalet
3 2
farm , Kingstown
This Chestertown, Maryland farmhouse rental, situated on a 127-acre organic farm along the Chester River, is 15 minutes from historic Chestertown and a quarter-mile from the owners' home. The three-bedroom, two-bathroom chalet features a large wraparound deck with river views, a fully equipped kitchen, a private dock with kayaks, and access to miles of hiking trails; it sleeps six and includes a microwave, dishwasher, and air conditioning.
Best Chesapeake Bay unique accommodations with a garden
9.8 252 reviews
Chesapeake Bay
09/12 – 09/16
$344/nighttotal: $1376 (4 )
Hideaway On The Bay: Waterfront Vintage A Frame
1 2
cabin , Long Beach
This charming cabin is located in Lusby, Maryland, just an hour's drive from Washington D.C., offering a peaceful escape near the Chesapeake Bay. The cabin has consistently earned excellent ratings from guests for its location, cleanliness, and overall experience. The cozy cabin sleeps up to 5 guests and features a fully equipped kitchen with modern appliances. Enjoy kayaking, canoeing, fishing, and crabbing right from the property, relax by the fire pit, and take advantage of the nearby vineyards and nature park.
8.8 5 reviews
Chesapeake Bay
08/23 – 08/28
$478/nighttotal: $2390 (5 )
Peaceful Entire 4 Br 2 Ba Cabin With Ac, Wifi, Pond View, Recreational Room
4 2
cabin , Crisfield
This waterfront vacation home, located in Marion Station near Crisfield, Maryland, offers easy access to Jane Island State Park and a bike path, and is within a 30-minute drive of Chincoteague Island and the Wallops Flight Facility. This 1500-square-foot Crisfield rental boasts four bedrooms sleeping eight, two bathrooms, a full kitchen with dishwasher, a fireplace, a terrace, and parking, perfect for family gatherings near Somers Cove Marina and Wellington Beach.
9.6 14 reviews
Chesapeake Bay
09/12 – 09/16
$339/nighttotal: $1356 (4 )
Lakefront Lusby Home W/ Fire Pit: 3 Mi To Beach!
2 2
cabin , Chesapeake Ranch Estates
This cozy cabin is located in Lusby, Maryland, just a short drive from Calvert Cliffs State Park and Drum Point Lighthouse, making it a perfect base for exploring the area's natural beauty and historical landmarks. The 2,200 square foot cabin comfortably sleeps up to 10 guests in its two bedrooms and two bathrooms. The cabin offers a fully equipped kitchen, laundry facilities, and a spacious living area, perfect for relaxing after a day of exploring. Guests can enjoy the outdoors with a porch, patio, and a fire pit, and the cabin also has covered parking and internet access.
Chesapeake Bay
08/23 – 08/28
$439/nighttotal: $2195 (5 )
Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay!
2 2
cabin , Charlestown
This log lodge in Charlestown is situated 30 miles from the Old Dutch House in North East, 19 miles from Dayett Station, and 20 miles from the Tennis Court. This 400-square-foot vacation home offers 2 bedrooms, 1 bathroom, and accommodates up to 15 guests with amenities including a kitchenette, refrigerator, microwave, air conditioning, a hot tub, garden, fitness center, tennis court, and parking.
Frequently Asked Questions about unique stays in Chesapeake Bay
What attractions is Baie de Chesapeake famous for?
Chesapeake Bay is known for its beautiful beaches, like Ocean City and Assateague Island. You can also visit the Chesapeake Bay Maritime Museum in St. Michaels to learn about the region's rich maritime history.
What clothing or gear is recommended for the climate in Baie de Chesapeake?
Pack light, breathable clothing for the warm and humid summers. Don't forget your swimsuit and sunscreen! In the fall and spring, you'll need layers as the weather can be unpredictable. And in the winter, pack warm clothes and a jacket.
What are the best ways to travel to Baie de Chesapeake eco-consciously?
To travel eco-consciously, consider taking the train to Baltimore or Washington, D.C., then renting a car. You can also explore the Bay by bike or kayak, which are great ways to enjoy the scenery and get some exercise.
Which neigbourhood offers the best unique stays in Baie de Chesapeake?
St. Michaels is a great place to find unique stays. The town has a variety of charming inns and bed and breakfasts, as well as waterfront cottages and vacation rentals.
What should you know about unique stays in Baie de Chesapeake before booking?
Before booking a unique stay, check the reviews and make sure it's the right fit for you. Some unique stays may be more remote or have limited amenities, so it's important to do your research.
Destinations nearby
Find the Best Unique Stays with a Hot Tub in Chesapeake Bay
These unique stays in Chesapeake Bay feature private hot tubs, perfect for a private soak after a day by the water.
Chesapeake Bay
09/12 – 09/16
$600/nighttotal: $2400 (4 )
Lakefront Cabin Near Solomons Island W/ Hot Tub
3 2
cabin , Chesapeake Ranch Estates
This lakefront vacation home in Lusby, Chesapeake Ranch Estates, offers direct beach access and lake views, located 5.5 miles from Annmarie Garden and 6.4 miles from Calvert Marine Museum. This three-bedroom, two-bathroom residence spans 1860 square feet, accommodating up to 23 guests with a fully equipped kitchen, hot tub, private patio, and free Wi-Fi.
10 103 reviews
Chesapeake Bay
09/12 – 09/16
$557/nighttotal: $2228 (4 )
Bayfront Walk-out Beach Home | Sunrise & Fire Pit
1 2
cabin , Drum Point
This modern log cabin is located in Drum Point, Maryland, on the Chesapeake Bay, just by the outlet of the Patuxent River, offering a picturesque setting. The property has received excellent ratings for location, cleanliness, and user experience. The cabin features three bedrooms and two bathrooms, accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a hot tub, a fire pit, a garden, and kayaks for exploring the surrounding waters.
9.7 422 reviews
Chesapeake Bay
08/23 – 08/28
$244/nighttotal: $1220 (5 )
Cozy Modern Chesapeake Bay Home
1 2
bungalow , Deale
This Deale bungalow sits right on the Chesapeake Bay, offering stunning sunset views and a relaxed atmosphere. It's highly rated by previous guests for its cleanliness, location, and overall experience. The two-bedroom home comfortably sleeps four guests and features a full kitchen, a private dock, and a jacuzzi. Enjoy kayaking, fresh seafood, and the beauty of the Chesapeake Bay right from your doorstep.
Best pet friendly Chesapeake Bay unique stays
Among the 481 accommodations in Chesapeake Bay, here are the 4 best pet friendly unique accommodations
10 1 review
Chesapeake Bay
07/20 – 07/27
$363/nighttotal: $2541 (7 )
Charming 2br With Fire Pit On Farm - 10 Min To Wharf
2 4
cabin , Bobtown
This two-bedroom farmhouse is located in Onancock, Virginia, offering a secluded rural retreat 5,280 feet from Onancock Wharf's shops and dining, and a 10-minute drive from historical sites like Ker Place Museum. This 900 square foot cottage accommodates four guests with two upstairs bedrooms, features a full kitchen with a fridge and microwave, air conditioning, WiFi, a working fireplace, an outdoor grill and fire pit, and welcomes pets.
Chesapeake Bay
10/01 – 10/05
$411/nighttotal: $1644 (4 )
The Heirloom Barn - Sleep Inside Living History
2 3
farm , Bel Air South
This restored Amish barn offers an upscale glamping retreat in Bel Air South, conveniently located just off I-95, providing easy access to Gunpowder Falls State Park and Susquehanna State Park. This unique farm stay accommodates up to six guests with two bedrooms and one bathroom, featuring a fire pit and a pavilion for communal gatherings, and offers an authentic historical experience.
9.8 18 reviews
Chesapeake Bay
09/12 – 09/16
$467/nighttotal: $1868 (4 )
Charming 2-bedroom Cabin Close To Fair Hill On Horse Farm
2 2
cabin , Elkton
This Elk Neck, Maryland cabin near Elkton provides easy access to Elkton Golf and Batting Center and Fred Rust Ice Arena. This two-bedroom, three-bathroom lodge comfortably sleeps thirteen guests, offering amenities such as air conditioning, internet, and a jetted tub, plus proximity to shopping at Newark Shopping Center and Castle Mall.
9.2 15 reviews
Chesapeake Bay
09/12 – 09/16
$521/nighttotal: $2084 (4 )
Maryland Vacation Rental W/ Private Pool & Dock
4 2
cabin , Long Beach
This Long Beach waterfront home is situated near Vera's White Sands Marina (0.8 miles) and Flag Ponds Nature Park (2.8 miles), with BGE Field and Calvert Cliffs State Park within 6 miles. This 2000-square-foot vacation rental boasts five bedrooms, two bathrooms, accommodates eleven guests, and features a private pool, fully equipped kitchen, and terrace—perfect for enjoying Long Beach's outdoor recreation.
Browse Waterfront Unique Stays in Chesapeake Bay
Plan an eccentric holiday at coastal unique stays in Chesapeake Bay, situated short distances from regional beach-town boardwalks.
8.8 4920 reviews
Chesapeake Bay
08/23 – 08/28
$267/nighttotal: $1335 (5 )
The Schooner Inn
1 2
hotel , Virginia Beach
Explore Unusual Accommodations with Swimming Pool in Chesapeake Bay
Every unique stay near the water in Chesapeake Bay includes a pool to complement your time by the shore.
Chesapeake Bay
06/20 – 06/27
$2145/nighttotal: $15015 (7 )
Remarkable Waterfront Property On 270 Acres
5 13
farm , Madison
8.8 5 reviews
Chesapeake Bay
09/12 – 09/16
$276/nighttotal: $1104 (4 )
Sailboat Experience In Annapolis
1 2
boat , Annapolis
10 24 reviews
Chesapeake Bay
07/20 – 07/27
$810/nighttotal: $5670 (7 )
Luxe Houseboat: Breathtaking Skyline 360 Views
1 4
houseboat , Baltimore
10 15 reviews
Chesapeake Bay
10/01 – 10/05
$869/nighttotal: $3476 (4 )
Luxe Houseboat With Epic 360 Views Of Baltimore Harbor