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

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.

6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino - Chesapeake Bay
9.8 8 reviews

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

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.
Welcome To Mermaid Haven! - Chesapeake Bay
9.7 64 reviews

Welcome To Mermaid Haven!

bungalow, Rock Hall
This Rock Hall vacation home is conveniently located within a mile of The Mainstay, Waterman’s Museum, and Rock Hall Harbor, offering easy access to the town's charming shops, restaurants, and attractions. Guests consistently rate this property excellent for its location, cleanliness, and overall experience.
This 3-bedroom, 2-bathroom house comfortably accommodates up to 9 guests in its 2000 square feet of space. Enjoy the amenities, including a swimming pool, jacuzzi, garden, and barbecue grills, perfect for relaxing and entertaining.
Awesome Private Off Grid Cabin With Creek View. - Chesapeake Bay
9.8 20 reviews

Awesome Private Off Grid Cabin With Creek View.

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.
The Tilghman Island Inn - Chesapeake Bay
9.3 76 reviews

The Tilghman Island Inn

island, Tilghman Island
Tilghman Island Inn is situated on Tilghman Island, a 5-minute walk from the Chesapeake Bay and Tilghman Island Marina, and 0.2 miles (approximately 1,056 feet) from Chesapeake Bay (North).
This inn offers complimentary Wi-Fi, on-site parking, a restaurant, a bar, a seasonal outdoor pool, and bicycle rentals, with grab-and-go breakfast available daily.

Best Chesapeake Bay unique accommodations with a garden

Luxe Houseboat With Epic 360 Views Of Baltimore Harbor - Chesapeake Bay
10 15 reviews

Luxe Houseboat With Epic 360 Views Of Baltimore Harbor

houseboat, Baltimore
FLOHOM 2 | Modern Charm is a houseboat docked at Port Covington Marina, a short walk from the up-and-coming district's restaurants and a quick water taxi ride to the Sagamore Spirit Distillery. This highly-rated houseboat offers a unique perspective on Baltimore, with panoramic views of the city skyline.
The houseboat features one bedroom and two bathrooms, comfortably accommodating up to four guests. Enjoy upscale amenities like a well-equipped kitchen, a spacious rooftop deck, and in-suite yoga mats, along with access to paddleboards, kayaks, and sailing tours.
Lakefront Lusby Home W/ Fire Pit: 3 Mi To Beach! - Chesapeake Bay
9.4 17 reviews

Lakefront Lusby Home W/ Fire Pit: 3 Mi To Beach!

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.
Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields - Chesapeake Bay
10 10 reviews

Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields

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.
Fully Equipped Docked Houseboat At Log Pond Marina In Havre De Grace, Md. - Chesapeake Bay
9.6 37 reviews

Fully Equipped Docked Houseboat At Log Pond Marina In Havre De Grace, Md.

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.

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.

Popular destinations

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.

Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay! - Chesapeake Bay
No reviews

Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay!

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.
Cozy Modern Chesapeake Bay Home - Chesapeake Bay
9.7 434 reviews

Cozy Modern Chesapeake Bay Home

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.
Lakefront Cabin Near Solomons Island W/ Hot Tub - Chesapeake Bay
No reviews

Lakefront Cabin Near Solomons Island W/ Hot Tub

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.

Best pet friendly Chesapeake Bay unique stays

Among the 354 accommodations in Chesapeake Bay, here are the 4 best pet friendly unique accommodations

Black Luxury Cabin Fire Pitgame Room.10 Guests - Chesapeake Bay
10 1 review

Black Luxury Cabin Fire Pitgame Room.10 Guests

cabin, Long Beach
This 4-bedroom, 3-bathroom cabin near Long Beach accommodates up to 10 guests and is located within 2 miles of Cove Point Lighthouse and Drum Point Lighthouse, offering convenient access to Vera's White Sands Marina and Chesapeake Hills Golf Course.
This rental features a sofa bed in the living room, air conditioning, and internet, with nearby attractions including the Annmarie Sculpture Garden and Arts Center and the Calvert Marine Museum.
Maryland Vacation Rental W/ Private Pool & Dock - Chesapeake Bay
9.4 16 reviews

Maryland Vacation Rental W/ Private Pool & Dock

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.
1st Floor 2 Br Cottage Walking To Beach - Chesapeake Bay
9.2 82 reviews

1st Floor 2 Br Cottage Walking To Beach

bungalow, Virginia Beach
This Virginia Beach vacation rental is located just a short walk from Pacific Avenue and the Virginia Beach Boardwalk, offering easy access to the area's attractions and entertainment. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 2-bedroom, 1-bathroom house can comfortably accommodate up to 4 guests. It comes equipped with a full kitchen, a private water park, a swimming pool, a spa, and a garden, providing ample space for relaxation and entertainment.
Solomons Island 6br Family Getaway - Chesapeake Bay
No reviews

Solomons Island 6br Family Getaway

island, Solomons
This Solomons cabin is located in a residential area, 1 kilometer (approximately 0.62 miles) from the town center and within walking distance of the Drum Point Lighthouse.
This accommodation offers a tranquil or active vacation with a fridge, microwave oven, dishwasher, air conditioning, garden, parking, and complimentary Wi-Fi, accommodating up to two guests.

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.

La Quinta Inn & Suites By Wyndham Baltimore N / White Marsh - Chesapeake Bay
No reviews

La Quinta Inn & Suites By Wyndham Baltimore N / White Marsh

farm, Rossville

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.

Lodge ∙ 1 Bedroom ∙ 2 Guests - Chesapeake Bay
No reviews

Lodge ∙ 1 Bedroom ∙ 2 Guests

chalet, Rock Hall
Luxe Houseboat: Breathtaking Skyline 360 Views - Chesapeake Bay
10 26 reviews

Luxe Houseboat: Breathtaking Skyline 360 Views

houseboat, Baltimore
Stunning Views From Waterfront Log Cabin With Fireplace On The Chesapeake Bay - Chesapeake Bay
10 183 reviews

Stunning Views From Waterfront Log Cabin With Fireplace On The Chesapeake Bay

cabin, Calvert Beach
Coles Point Marina - Chesapeake Bay
No reviews

Coles Point Marina

cabin, Montross
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