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Chesapeake Bay unique stays
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481 Unique places to stay in Chesapeake Bay

El  Camino - Chesapeake Bay
10 54 reviews
Chesapeake Bay
07/02 – 07/05
$257/nighttotal: $771 (3 )

El Camino

1 2
cabin, Piney Point
This Piney Point waterfront cottage is located less than a mile from Cardinal Gibbons Park and First District Community Park, and about 3 miles from Saint Inigoes State Forest, offering easy access to outdoor recreation. This one-bedroom, one-bathroom getaway sleeps three guests and features a fully equipped kitchen, Smart TV, barbecue grill, and a terrace with stunning water views.
The Heirloom Barn -  Sleep Inside Living History - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$314/nighttotal: $2198 (7 )

The Heirloom Barn - Sleep Inside Living History

2 2
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.
Lovin’ Life | Floating Getaway On Sue Creek - Chesapeake Bay
10 17 reviews
Chesapeake Bay
07/02 – 07/05
$253/nighttotal: $759 (3 )

Lovin’ Life | Floating Getaway On Sue Creek

1 2
barge, Essex
This unique houseboat, situated in Baltimore's Essex neighborhood on Sue Creek within the Baltimore Boating Center, offers easy access to Charley's Lawns and Waterfront Restaurant.
The one-bedroom, one-bathroom vessel sleeps two and features a full kitchen with fridge, freezer, and microwave, a rooftop deck, SmartTV, Wi-Fi, and air conditioning, plus access to a nearby bathhouse; enjoy nearby paddleboarding and contribute to Przewalski's horse conservation with your stay.
New, Chic River Bungalow In Historic District - Chesapeake Bay
9.7 7 reviews
Chesapeake Bay
08/29 – 09/05
$211/nighttotal: $1477 (7 )

New, Chic River Bungalow In Historic District

1 2
bungalow, Cambridge
This Cambridge, England bungalow, a renovated former flower shop, is located one block from the River Cam and a five-minute walk from Cambridge's revitalized city center, offering easy access to shops, galleries, and restaurants.
This two-bedroom, two-bathroom house sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a dedicated workspace, and a private garden; a fitness center and parking are also available.
Waterfront Lancaster Cabin ~ 10 Mi To Kilmarnock! - Chesapeake Bay
8.8 4 reviews
Chesapeake Bay
08/29 – 09/05
$385/nighttotal: $2695 (7 )

Waterfront Lancaster Cabin ~ 10 Mi To Kilmarnock!

3 2
cabin, Lancaster
This Lancaster County cabin, located approximately 62 miles from Newport News/Williamsburg International Airport, offers a convenient base for exploring the region. This 1600-square-foot retreat sleeps up to 11 guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, and in-unit laundry.
Fisherman's Cabin On The Bay - Chesapeake Bay
8.8 26 reviews
Chesapeake Bay
07/30 – 08/05
$450/nighttotal: $2700 (6 )

Fisherman's Cabin On The Bay

3 6
cabin, Norfolk
This Norfolk cabin is located just a short block from the marina and a couple of blocks from the Chesapeake Bay's sandy beaches, offering easy access to waterfront activities and attractions. Guests consistently rate this rental as "very good," highlighting its comfortable accommodations and prime location.
The single-story home features 1450 square feet of space, comfortably accommodating up to seven guests in its three bedrooms and one bathroom. Enjoy modern amenities like a large 65" Smart TV, high-speed WiFi, a fully equipped kitchen, a charcoal grill, a fireplace, and a spacious garden perfect for relaxing and enjoying the beautiful sunsets over the Chesapeake Bay.
A Little Slice Of Heaven On The Choptank River. - Chesapeake Bay
10 29 reviews
Chesapeake Bay
07/30 – 08/05
$405/nighttotal: $2430 (6 )

A Little Slice Of Heaven On The Choptank River.

2 6
chalet, Cambridge
This charming cottage is located in East New Market, just across from the Hyatt Resort and a short distance from downtown Cambridge's attractions and restaurants. The chalet has received excellent user ratings, making it a popular choice for travelers.
The cottage features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy access to a private waterfront location with a terrace, a garden, and a kitchen equipped with a fridge and microwave, plus amenities like air conditioning.
Waterfront Cabin! Dock, Crab, Paddle, Kayak, Outdoor Movie, Karaoke, And More! - Chesapeake Bay
10 8 reviews
Chesapeake Bay
07/05 – 07/08
$515/nighttotal: $1545 (3 )

Waterfront Cabin! Dock, Crab, Paddle, Kayak, Outdoor Movie, Karaoke, And More!

3 4
cabin, Heathsville
This Heathsville waterfront cottage is located within two miles of the Heathsville Farmers' Market and Rice's Hotel/Hughlett's Tavern, and nine miles from the Northern Neck Farm Museum and Bush Mill Stream Natural Area Preserve.
This three-bedroom, two-bathroom vacation rental sleeps eight, features a fully equipped kitchen with a dishwasher, offers free Wi-Fi, and includes an on-site arcade/game room.
Fisherman's Cabin - Water Front And Pet Friendly By Redawning - Chesapeake Bay
8.6 17 reviews
Chesapeake Bay
07/30 – 08/05
$442/nighttotal: $2652 (6 )

Fisherman's Cabin - Water Front And Pet Friendly By Redawning

3 6
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.
2-bedroom Lake-house With A Magnificent View - Chesapeake Bay
9.6 201 reviews
Chesapeake Bay
07/05 – 07/08
$346/nighttotal: $1038 (3 )

2-bedroom Lake-house With A Magnificent View

2 4
cabin, Drum Point
This Drum Point cabin is located just a short walk from the bay beach, offering stunning sunrise and sunset views. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cabin comfortably sleeps six guests in its two bedrooms and two bathrooms. You'll find a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, a peaceful garden, and a relaxing hot tub, all perfect for a memorable stay.
Family Retreat At Lansdowne Manor - Chesapeake Bay
10 12 reviews
Chesapeake Bay
07/05 – 07/08
$597/nighttotal: $1791 (3 )

Family Retreat At Lansdowne Manor

4 4
farm, Centreville
This Centreville farm stay, a 3,500-square-foot rural rental, is conveniently located within 9-12 miles of attractions like the Hazel Miner Monument, Tuckahoe State Park, Adkins Arboretum, Church Hill Theatre, and Cassinelli Winery and Vineyards.
The four-bedroom, three-bathroom house sleeps eight and offers amenities including air conditioning, a full kitchen with dishwasher, internet access, pet-friendliness, and ample parking.
Flohom 3 | Tiny Houseboat•fire Pit•magothy River - Chesapeake Bay
9.9 75 reviews
Chesapeake Bay
07/02 – 07/05
$514/nighttotal: $1542 (3 )

Flohom 3 | Tiny Houseboat•fire Pit•magothy River

1 2
barge, Arnold
FLOHOM 3, a unique floating tiny home situated at Ferry Point Marina on the Magothy River in Arnold, Maryland, offers easy access to the river and nearby attractions.
This one-bedroom, one-bathroom houseboat sleeps two guests and features a full kitchenette, a rooftop deck with 360-degree views, on-site yoga mats, and a dedicated parking spot; guests also have access to a guest app with local guides and booking options.

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.

Pizza Friday - Chesapeake Bay
10 9 reviews
Chesapeake Bay
08/29 – 09/05
$474/nighttotal: $3318 (7 )

Pizza Friday

4 2
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.
6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino - Chesapeake Bay
10 7 reviews
Chesapeake Bay
08/29 – 09/05
$841/nighttotal: $5887 (7 )

6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino

6 2
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.
Kent Island Resort - Chesapeake Bay
Chesapeake Bay
07/02 – 07/05
$407/nighttotal: $1221 (3 )

Kent Island Resort

1 2
island, Stevensville
Kent Island Resort is located in Stevensville, Maryland, just a 15-minute drive from the Chesapeake Bay Bridge and Queenstown Premium Outlets. The resort offers a waterfront location with stunning views of the Chesapeake Bay, making it a perfect choice for a relaxing getaway. This charming resort features a Victorian design and offers a variety of amenities, including a swimming pool, garden, restaurant, bar, and meeting space. Guests can enjoy outdoor recreation, complimentary internet access, and convenient room service.
Awesome Private Off Grid Cabin With Creek View. - Chesapeake Bay
9.8 19 reviews
Chesapeake Bay
08/29 – 09/05
$185/nighttotal: $1295 (7 )

Awesome Private Off Grid Cabin With Creek View.

2 2
cabin, Bayside
This Bayside cabin is centrally located in Onancock and within easy reach of major tourist attractions. It has an excellent user rating.
The cabin has 2 bedrooms, 1 bathroom, a kitchen, and a living room. It can accommodate up to 6 guests and has a floor area of 530 square feet. The cabin is pet-friendly, family-friendly, and has air conditioning. It also has a terrace, a garden, and parking.

Best Chesapeake Bay unique accommodations with a garden

Lovin Life ! - Chesapeake Bay
10 1 review
Chesapeake Bay
07/02 – 07/05
$307/nighttotal: $921 (3 )

Lovin Life !

1 2
houseboat, Essex
The houseboat rental "Lovin’ Life!" is located in Essex, Maryland, near the National Aquarium in Baltimore, the Baltimore Cruise Terminal, and the Baltimore Inner Harbor Marina, though precise distances aren't provided.
This one-bedroom, two-bathroom floating home accommodates two guests and offers a unique waterside experience in Essex, with potential access to nearby attractions and water activities (amenities not specified).
Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields - Chesapeake Bay
10 9 reviews
Chesapeake Bay
07/30 – 08/05
$352/nighttotal: $2112 (6 )

Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields

4 6
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.
Dock & Bay Access! Cabin On St. Jeromes Creek - Chesapeake Bay
9.2 22 reviews
Chesapeake Bay
08/29 – 09/05
$338/nighttotal: $2366 (7 )

Dock & Bay Access! Cabin On St. Jeromes Creek

2 2
cabin, Piney Point
This waterfront cottage in Ridge, MD, offers direct access to St. Jerome's Creek and the Chesapeake Bay, located 7 miles from Historic St. Mary's City and Point Lookout Lighthouse.
This 1260 sq ft cabin accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, a wood-burning fireplace, complimentary kayaks, a private boat dock, and a covered deck with water views.
Peaceful Spacious Lake House Cabin - Chesapeake Bay
10 1 review
Chesapeake Bay
07/02 – 07/05
$313/nighttotal: $939 (3 )

Peaceful Spacious Lake House Cabin

3 2
cabin, Chesapeake Ranch Estates
This rustic log lodge is located directly on the Chesapeake Bay in Southern Maryland, offering waterfront access and proximity to community private beaches for kayaking, paddleboarding, and fishing, with hiking trails, historic sites in Lusby and Solomons Island, and local restaurants, vineyards, and festivals nearby. This lodge accommodates up to 8 guests and features a gourmet kitchen, air conditioning, Wi-Fi, a garden, parking, two bathrooms, a fire table, and a grill on the back patio with water views, situated approximately 1.5 hours from Washington D.C. and Baltimore.

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.

Cozy Modern Chesapeake Bay Home - Chesapeake Bay
9.7 422 reviews
Chesapeake Bay
08/29 – 09/05
$193/nighttotal: $1351 (7 )

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.
Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay! - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$435/nighttotal: $3045 (7 )

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.

Best pet friendly Chesapeake Bay unique stays

Among the 481 accommodations in Chesapeake Bay, here are the 4 best pet friendly unique accommodations

Cozy Historic Cabin On The Water - Chesapeake Bay
9.8 30 reviews
Chesapeake Bay
07/02 – 07/05
$430/nighttotal: $1290 (3 )

Cozy Historic Cabin On The Water

1 2
cabin, Grasonville
This charming 1787 cabin is located near Grasonville, Maryland, just a short drive from the scenic Wye River and within easy reach of Washington, D.C. The property has received excellent ratings for location, cleanliness, and overall experience.
This cozy cottage features one bedroom and two bathrooms, comfortably accommodating two guests. Enjoy the private dock, man-made beach, and ample space for fishing, all while immersing yourself in the tranquility of nature.
Cabin On The Creek ~ Kayaks And Fire Pit - Chesapeake Bay
9.9 111 reviews
Chesapeake Bay
07/05 – 07/08
$461/nighttotal: $1383 (3 )

Cabin On The Creek ~ Kayaks And Fire Pit

3 4
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.
Sailboat Experience In Annapolis - Chesapeake Bay
8.8 5 reviews
Chesapeake Bay
08/29 – 09/05
$222/nighttotal: $1554 (7 )

Sailboat Experience In Annapolis

1 2
boat, Annapolis
This Annapolis sailboat rental is a 10-minute walk from Annapolis Harbor, 22 miles from Baltimore/Washington International Thurgood Marshall Airport, and 31 miles from Carroll Park.
This 1610-square-foot vessel features one bedroom, one bathroom, accommodates four guests, and includes a full kitchen, air conditioning, Wi-Fi, and a seasonal outdoor pool.
The Whispering Rafters Tiny Home - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$281/nighttotal: $1967 (7 )

The Whispering Rafters Tiny Home

1 2
farm, Bel Air South
This historical farm stay in Bel Air offers a unique lodging experience within a restored 1760s enslaved quarters and chicken coop, providing a palpable connection to centuries of American history.
This sanctuary for two features air conditioning and internet, accommodates two guests, and is located a short drive from Gunpowder Falls State Park and Susquehanna State Park, with the Havre de Grace Maritime Museum also nearby.

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.

Luxe Houseboat With Epic 360 Views Of Baltimore Harbor - Chesapeake Bay
10 15 reviews
Chesapeake Bay
08/29 – 09/05
$734/nighttotal: $5138 (7 )

Luxe Houseboat With Epic 360 Views Of Baltimore Harbor

2 2
houseboat, Baltimore

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.

Flohom 14 | Chesapeake Bay • Pool & Beach Access - Chesapeake Bay
10 23 reviews
Chesapeake Bay
07/02 – 07/05
$740/nighttotal: $2220 (3 )

Flohom 14 | Chesapeake Bay • Pool & Beach Access

1 2
barge, Lake Shore
Remarkable Waterfront Property On 270 Acres - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$2198/nighttotal: $15386 (7 )

Remarkable Waterfront Property On 270 Acres

5 2
farm, Madison
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