Chesapeake Bay unique stays

Compare unique places in Chesapeake Bay from 100+ sites!

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

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Price per night
Accommodation type
Rating

689 Unique places to stay in Chesapeake Bay

Quiet Cottage On Wooded Property - Chesapeake Bay
9.4Excellent 25 reviews
Chesapeake Bay
2 1
$136/nighttotal: $544 (4 )

Quiet Cottage On Wooded Property

bungalow - Long Beach
Bungalow listing for up to 2 guests with an excellent rating of 94% based on 25 reviews. You will be based in Long Beach.
Facilities and services: a freeze, a kitchen and a washing machine.
Cozy Modern Chesapeake Bay Home - Chesapeake Bay
9.7Excellent 346 reviews
Chesapeake Bay
2 2
$252/nighttotal: $1008 (4 )

Cozy Modern Chesapeake Bay Home

bungalow - Deale
Bungalow for 4 guests with an excellent rating of 97% based on 346 reviews. Your accommodation will be based in Deale.
Facilities and services include air conditioning, an iron and a garden. This accommodation in Deale also has a Jacuzzi to relax in!
Dolce Vida -Kent Island Home With Pool And Ocean View-sleeps 10-12-pets Allowed - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 4
$1819/nighttotal: $7276 (4 )

Dolce Vida -Kent Island Home With Pool And Ocean View-sleeps 10-12-pets Allowed

island - Chester
This island is situated on Kent Island in Maryland, surrounded by the Chesapeake Bay and within a 2-hour drive of popular beaches like Dewey, Rehoboth, and Ocean City. The house offers stunning views of the Chesapeake Bay and easy access to water activities.
The house features 4 bedrooms, 3 full baths, a family room, a living room, and a separate dining area. The house can accommodate up to 10 guests and has a floor area of 3000 square feet. The house has received excellent user ratings. The house offers a range of amenities, including a private pool, a fully equipped kitchen, and a private pier. Guests can also enjoy activities such as crabbing, swimming, and biking.
1943 Beach House Walk To Town & Beach & Boardwalk. - Chesapeake Bay
9.9Excellent 27 reviews
Chesapeake Bay
2 2
$237/nighttotal: $948 (4 )

1943 Beach House Walk To Town & Beach & Boardwalk.

cabin - North Beach
This North Beach cabin is ideally situated in the heart of the town, within walking distance of restaurants and the waterfront. It has received excellent ratings for its location, cleanliness, and user experience.
The cabin has 2 bedrooms and 1 bathroom, with a guest capacity of 4. It features a fully equipped kitchen, air conditioning, a private backyard with a screened porch, and on-site parking. Guests can enjoy the outdoor seating areas, barbecue facilities, and proximity to the beach.
Pizza Friday - Chesapeake Bay
10Excellent 24 reviews
Chesapeake Bay
2 4
$506/nighttotal: $2024 (4 )

Pizza Friday

cabin - Piney Point
Cabin rental for 10 people with an excellent rating of 100% based on 24 reviews. This accommodation is based in Piney Point.
Services and facilities: a barbecue, a washing machine and a fridge. Take advantage of the Free Parking with this accommodation.
Awesome Private Off Grid Cabin With Creek View. - Chesapeake Bay
9.3Excellent 15 reviews
Chesapeake Bay
2 2
$278/nighttotal: $1112 (4 )

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.
Cabin On The Creek - Chesapeake Bay
10Excellent 5 reviews
Chesapeake Bay
2 2
$328/nighttotal: $1312 (4 )

Cabin On The Creek

cabin - Madison
Cabin for 4 people with an excellent rating of 100% based on 5 reviews. This accommodation is based in Madison.
Services and facilities: a washing machine, free parking and air conditioning.
La Cabaña - Chesapeake Bay
9.7Excellent 30 reviews
Chesapeake Bay
2 1
$253/nighttotal: $1012 (4 )

La Cabaña

cabin - Nanticoke Acres
Cabin for up to 5 guests with an excellent rating of 97% based on 30 reviews. This accommodation is located in Nanticoke Acres.
Facilities and services: a barbecue, air conditioning and free parking. Take advantage of the garden in this accommodation in Nanticoke Acres.
Pizza Friday - Chesapeake Bay
10Excellent 4 reviews
Chesapeake Bay
2 4
$555/nighttotal: $2220 (4 )

Pizza Friday

cabin - Piney Point
This secluded waterfront cabin in Saint Inigoes offers a peaceful retreat with stunning water views from almost every room and a private dock for relaxation and water exploration. Just 30 minutes from supermarkets and St. Mary's College of Maryland, the cabin has received excellent user ratings.
The cabin features 4 bedrooms, 2 bathrooms, and can accommodate up to 10 guests. Inside, the cozy and inviting interior is flooded with natural light from large picture windows, while outside, guests can enjoy a brand new pizza oven, a spacious dock, and nearby hiking trails and beaches.
Kent Island Time - Waterfront - Chesapeake Bay
10Excellent 6 reviews
Chesapeake Bay
2 2
$716/nighttotal: $2864 (4 )

Kent Island Time - Waterfront

island - Chester
This waterfront vacation home on Kent Island in Chester offers stunning views of Crab Alley Bay and sunsets, and a private pier for crabbing and fishing. It's close to cultural attractions like the Pickering Creek Audubon Center and Chesapeake Bay Maritime Museum, and recreational activities like Queenstown Harbor Golf Links and Golf Club.
The island has an excellent user rating, and features two bedrooms, two bathrooms, and a guest capacity of eight. It has a cozy interior with two living spaces and a fully equipped kitchen, as well as a large patio with a picnic table and ample seating. The island also has air conditioning, a jacuzzi, a garden, a spa, and parking.
Cozy Home On The Beautiful Delaware Countryside. - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 4
$623/nighttotal: $2492 (4 )

Cozy Home On The Beautiful Delaware Countryside.

farm - Bridgeville
Farm from 441 dollars per night for 8 people with an excellent rating of 100% based on 1 reviews. This accommodation is based in Bridgeville.
Facilities and services: a terrace, a dish washer and a fridge. Take advantage of the garden in this accommodation in Bridgeville.
Quailsar Farm | An Esvr Property - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 5
$1232/nighttotal: $4928 (4 )

Quailsar Farm | An Esvr Property

farm - Easton
Farm rental from 656 dollars per night for up to 10 people with an excellent rating of 100% based on 1 reviews. You will be located in Easton.
Services and facilities include free parking, a dish washer and a washing machine. This is a pet-friendly accommodation!

Other accommodation types in Chesapeake Bay

Best Chesapeake Bay unique stays with a jacuzzi

Among the 689 accommodations in Chesapeake Bay, here are the 1 best unique accommodations with a jacuzzi

Bayside House With Sunset Water Views On Secluded Private Farm - Chesapeake Bay
Chesapeake Bay
2 3
$456/nighttotal: $1824 (4 )

Bayside House With Sunset Water Views On Secluded Private Farm

farm - Bobtown
This 513+ acre waterfront farm in Onancock offers a secluded retreat on the Eastern Shore of Virginia. The 1,278 square foot home has 3 bedrooms, 2 bathrooms, an eat-in kitchen, laundry room, and family room.
Guests can enjoy the waterfront fire pit and deck with Chesapeake Bay views, as well as boating and fishing opportunities in the Chesapeake Bay and nearby creeks. The farm is also close to cultural attractions like Red Queen Gallery and North Street Playhouse, as well as North Street Market and SouthEast Expeditions for outdoor adventures.

Best family friendly Chesapeake Bay unique stays

Among the 689 accommodations in Chesapeake Bay, here are the 4 best family friendly unique accommodations

Get Away To Relax On Smith Island In The Chesapeake Bay - Chesapeake Bay
10Excellent 2 reviews
Chesapeake Bay
2 1
$192/nighttotal: $768 (4 )

Get Away To Relax On Smith Island In The Chesapeake Bay

island - Smith Island
This 1-bedroom, 1-bathroom vacation home is located on Smith Island, Maryland, offering a unique and tranquil retreat. It features a cozy ambiance with a spacious bedroom, comfortable living area, and enclosed patio.
The home boasts excellent user ratings and is family-friendly, with amenities such as air conditioning, a fully equipped kitchen, and a waterfront access for kayaking, stand-up paddleboarding, or biking. It can accommodate up to 3 guests and is available for rent as "Smith Island".
New Island Home On The Chesapeake Bay Sunsets - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 5
$940/nighttotal: $3760 (4 )

New Island Home On The Chesapeake Bay Sunsets

island - Taylors Island
Island from 553 dollars per night for 12 people with an excellent rating of 100% based on 1 reviews. Your accommodation will be located in Taylors Island.
Facilities and services: a terrace, a barbecue and a washing machine. You can bring your favorite pets this accommodation!
Woodland Retreat On Kent Island: 5 Beds, 5 Miles From Bay Bridge, On 5 Acres. - Chesapeake Bay
Chesapeake Bay
2 4
$793/nighttotal: $3172 (4 )

Woodland Retreat On Kent Island: 5 Beds, 5 Miles From Bay Bridge, On 5 Acres.

island - Stevensville
Island from 372 dollars per night for up to 10 guests. You will stay in Stevensville.
Facilities and services: a pool table, an elevator and a kitchen. Take advantage of the Free Parking with this accommodation in Stevensville!
Luxe Chesapeake Cabin * River View* Fire Pit* - Chesapeake Bay
Chesapeake Bay
2 3
$338/nighttotal: $1352 (4 )

Luxe Chesapeake Cabin * River View* Fire Pit*

cabin - Shady Side
Nestled in the tranquil ambiance of Shady Side, Luxe Chesapeake Cabin offers a serene riverfront retreat just 35 km from the historic Annapolis Harbor. The spacious 1080-square-foot cabin accommodates up to 9 guests in its 3 bedrooms and 1 bathroom layout.
Featuring a fully equipped kitchen, air conditioning, and a private terrace, the cabin provides a comfortable and convenient stay. Guests can enjoy outdoor dining, soak in the picturesque river views, or gather around the fire pit for cozy evenings under the stars.

Destinations nearby

Best pet friendly Chesapeake Bay unique stays

Among the 689 accommodations in Chesapeake Bay, here are the 5 best pet friendly unique accommodations

Beautiful Home In Walkable Beach Town Near Dc & Herrington Harbor Yacht Club! - Chesapeake Bay
8.0Very good 1 review
Chesapeake Bay
2 3
$392/nighttotal: $1568 (4 )

Beautiful Home In Walkable Beach Town Near Dc & Herrington Harbor Yacht Club!

yacht - North Beach
This North Beach yacht is located in a charming waterfront town with walking distance to the beach, pier, and boardwalk. It has a very good user rating. The 1680 square feet, 3-bedroom, 3-bathroom yacht can accommodate up to 9 guests. It features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a garden, and parking.
Six Bedroom 2020 Fountaine Pajot Catamaran - Chesapeake Bay
Chesapeake Bay
2 6
$1380/nighttotal: $5520 (4 )

Six Bedroom 2020 Fountaine Pajot Catamaran

houseboat - Riva
This six-bedroom, six-bathroom houseboat is located on the South River in Edgewater, just miles from downtown Annapolis. It offers a unique location on the water with stunning views and easy access to the historic city.
The houseboat has a spacious layout with six bedrooms and six bathrooms, providing ample space for groups or families. It includes a full kitchen, living area, and outdoor deck, as well as air conditioning and pet-friendly accommodations. Guests can also enjoy sailing excursions on the catamaran sailboat.
Luxurious 50 Ft. Fountaine Pajot Saba. Six Cabin Six Head Layout. - Chesapeake Bay
Chesapeake Bay
2 6
$3081/nighttotal: $12324 (4 )

Luxurious 50 Ft. Fountaine Pajot Saba. Six Cabin Six Head Layout.

houseboat - Riva
This six-cabin, six-head houseboat is located in Edgewater, just a short distance from historical landmarks and popular attractions in Annapolis. It can accommodate up to 12 guests and features a fully equipped kitchen, three spacious outdoor lounging areas, and two paddle boards for exploring the surrounding waters.
The houseboat also offers stunning views of the Annapolis/Chesapeake area or Marsh Harbour Abacos Bahamas, and is conveniently located near historical landmarks, attractions, and outdoor activities. Whether you're looking for a relaxing getaway or an adventure-filled vacation, this houseboat is the perfect choice for your next trip to Riva.
The Blackwater Refuge Country House On A Quiet 12 Acres - Chesapeake Bay
10Excellent 1 review
Chesapeake Bay
2 2
$236/nighttotal: $944 (4 )

The Blackwater Refuge Country House On A Quiet 12 Acres

mountain refuge - Cambridge
Mountain refuge from 167 dollars per night for 6 people with an excellent rating of 100% based on 1 reviews. This accommodation is located in Cambridge.
Facilities and services: a garden, a washing machine and air conditioning. You can bring your favorite pets this accommodation!
Luxe Chesapeake Cabin House Near Lake - Chesapeake Bay
Chesapeake Bay
2 3
$413/nighttotal: $1652 (4 )

Luxe Chesapeake Cabin House Near Lake

cabin - Shady Side
Cabin listing from $237 for up to 11 guests. Your accommodation will be based in Shady Side.
Facilities and services: a washing machine, a kitchen and air conditioning. Take advantage of the Free Parking with this accommodation in Shady Side!