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Check prices for these dates

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Jul 18 - Jul 20
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Featured Cottages in Chesapeake Bay

Key West Cottages
Situated on a wooden dock, this house offers serene waterfront views from its balcony.

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (402)
"We had wonderful stay. Everything about this resort was perfect. "
Key West Cottages
Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage by RedAwning
Enjoy a serene beach experience surrounded by natural dunes and tall grasses.

Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage by RedAwning

3.5 star property
Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage by RedAwning
Hampton Home w/ Fireplace + Close to Beaches!
Enjoy meals with family and friends at this spacious dining area, featuring a large round table and comfortable seating for six.

Hampton Home w/ Fireplace + Close to Beaches!

3.0 star property
6.0 out of 10, (2)
"I traveled with my family from pennsylvania check in was held up with no one called about Dirty dishes dirty towels ripped up towels barely any wash cloths barely parking old food and rippers behind the beds major dust just horrible "
Hampton Home w/ Fireplace + Close to Beaches!
Walk to Beach: Hampton Home w/ Grill!
Interior

Walk to Beach: Hampton Home w/ Grill!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful communication with property owner, comfortable beds and amenities like a welcome basket with snacks/bottle water/juice was an added bonus. Very clean throughout and easy to follow check-in and out instructions. Only minor complaint is that the air conditioner for the upstairs room was off upon arrival, so the room was quite hot when we arrived near 8pm at night. Would definitely stay again as we were close walk to the beach and local food spots. "
Walk to Beach: Hampton Home w/ Grill!
Game Room + Gym: Downtown DC Home!
Relax on the outdoor deck with a long sofa, armchair, and coffee table, and enjoy the convenience of a barbecue grill.

Game Room + Gym: Downtown DC Home!

3.0 star property
Game Room + Gym: Downtown DC Home!
Pink Flamingo At The Beach 2 Bedroom Cottage by RedAwning
Relax in comfort on the beach with three chairs arranged for your convenience.

Pink Flamingo At The Beach 2 Bedroom Cottage by RedAwning

3.0 star property
Pink Flamingo At The Beach 2 Bedroom Cottage by RedAwning
Chincoteague Island Cottage ~ 2 Mi to Beaches
Enjoy meals at a round table with four chairs, each with a unique design, and take in the view from the large windows.

Chincoteague Island Cottage ~ 2 Mi to Beaches

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was great and it is very close to the beach area as well as the wild ponies. Walkable to all the coffee shops and ice cream. Only downside, if you cook there is nothing locally good to eat but won’t hold it against the area, just preference. People were great and coffee shops were great. "
Chincoteague Island Cottage ~ 2 Mi to Beaches
Walk to Dining: Sleek Hampton Home w/ Deck!
Interior

Walk to Dining: Sleek Hampton Home w/ Deck!

3.0 star property
Walk to Dining: Sleek Hampton Home w/ Deck!
3 Mi to Huntington Beach: Hampton Family Home!
Garage with workbench and tools, offering ample space for projects.

3 Mi to Huntington Beach: Hampton Family Home!

3.0 star property
3 Mi to Huntington Beach: Hampton Family Home!
6 Mi to Capitol Hill: Spacious Family Home in DC
Interior

6 Mi to Capitol Hill: Spacious Family Home in DC

3.0 star property
6 Mi to Capitol Hill: Spacious Family Home in DC
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Enjoy meals in the spacious dining area with a glass-top table and comfortable seating.

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
5 Mi to National Mall: DC Home w/ Pool Table
Interior

5 Mi to National Mall: DC Home w/ Pool Table

3.0 star property
5 Mi to National Mall: DC Home w/ Pool Table
Baltimore Home < 2 Mi to Dtwn Towson
Guests can enjoy a tranquil outdoor space with a metal railing, surrounded by landscaped grass and shrubs.

Baltimore Home < 2 Mi to Dtwn Towson

3.0 star property
Baltimore Home < 2 Mi to Dtwn Towson
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

How much do cottages in Chesapeake Bay cost?
Rates for cottages in Chesapeake Bay range between and per night. Whatever your budget, you're sure to find the perfect place to get in tune with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chesapeake Bay?
You can select from 11 cottages in Chesapeake Bay. Whether you're traveling with the kids, as a couple or with a group of close friends, Expedia makes it a breeze to find your ideal place.
Why book your cottage in Chesapeake Bay with Expedia?
Reserving a cottage in Chesapeake Bay is as easy as clicking on your travel dates and picking your ideal place for outdoor fun and relaxation. From upscale retreats to inexpensive properties and cottages that have amenities like a kitchenette, Expedia has something for all tastes. As for terrific deals? We've have them as well!