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Chesapeake Bay unique stays
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481 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.

Fully Equipped Docked Houseboat At Log Pond Marina In Havre De Grace, Md. - Chesapeake Bay
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.
6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino - Chesapeake Bay
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.
Rustic 3br Waterfront Cabin With Firepit + Dock Access - Chesapeake Bay
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.
Blue Heron Farm Waterfront Chalet - Chesapeake Bay
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

Hideaway On The Bay: Waterfront Vintage A Frame - Chesapeake Bay
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.
Peaceful Entire 4 Br 2 Ba Cabin With Ac, Wifi, Pond  View, Recreational Room - Chesapeake Bay
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.
Lakefront Lusby Home W/ Fire Pit: 3 Mi To Beach! - Chesapeake Bay
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.
Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay! - Chesapeake Bay
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.

Lakefront Cabin Near Solomons Island W/ Hot Tub - Chesapeake Bay
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.
Bayfront Walk-out Beach Home | Sunrise & Fire Pit - Chesapeake Bay
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.
Cozy Modern Chesapeake Bay Home - Chesapeake Bay
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

Charming 2br With Fire Pit On Farm - 10 Min To Wharf - Chesapeake Bay
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.
The Heirloom Barn -  Sleep Inside Living History - Chesapeake Bay
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.
Charming 2-bedroom Cabin Close To Fair Hill On Horse Farm - Chesapeake Bay
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.
Maryland Vacation Rental W/ Private Pool & Dock - Chesapeake Bay
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.

The Schooner Inn - Chesapeake Bay
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.

Remarkable Waterfront Property On 270 Acres - Chesapeake Bay
Chesapeake Bay
06/20 – 06/27
$2145/nighttotal: $15015 (7 )

Remarkable Waterfront Property On 270 Acres

5 13
farm , Madison
Sailboat Experience In Annapolis - Chesapeake Bay
8.8 5 reviews
Chesapeake Bay
09/12 – 09/16
$276/nighttotal: $1104 (4 )

Sailboat Experience In Annapolis

1 2
boat , Annapolis
Luxe Houseboat: Breathtaking Skyline 360 Views - Chesapeake Bay
10 24 reviews
Chesapeake Bay
07/20 – 07/27
$810/nighttotal: $5670 (7 )

Luxe Houseboat: Breathtaking Skyline 360 Views

1 4
houseboat , Baltimore
Luxe Houseboat With Epic 360 Views Of Baltimore Harbor - Chesapeake Bay
10 15 reviews
Chesapeake Bay
10/01 – 10/05
$869/nighttotal: $3476 (4 )

Luxe Houseboat With Epic 360 Views Of Baltimore Harbor

2 3
houseboat , Baltimore
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