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Featured Cottages in Chesapeake Bay and around

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (390)
"Clean, relaxing we throughly enjoyed our stay!"
Key West Cottages

Lovely backyard cottage with easy access to metro, shops, dining!

10.0 out of 10, Exceptional, (66)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (263)
"Great place to stay, neat little house. Property manager was very easy to chat with and very friendly. Would stay again!"
The price is €411
includes taxes & fees
20 Jul - 21 Jul
Norfolk Beach Cottage Rental

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (181)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (159)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (44)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Pink Flamingo at the Beach

9.0 out of 10, Wonderful, (15)
"older place but very nice and close to the beach"
Pink Flamingo at the Beach

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (6)
"Lovely home right on the river- fishing to your hearts content Clean, lots to do very peaceful!!! Would definitely come back! Mia is great to work with"
NEW PET FRIENDLY LISTING ALERT!!

Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

10.0 out of 10, Exceptional, (11)
"The house was tidy and clean, and had everything our family needed. The playground and pickleball courts next door were a plus for us! The easy walk to shops on Main Street was also nice. "
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg

Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg

Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

8.0 out of 10, Very good, (3)
"It was an amazing weekend everyone is so nice around. the house is older but beautifull place to stay with your family the beech is Absolutely amazing. Hope we can rent this special gem again in the future "
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

10.0 out of 10, Exceptional, (20)
"We were very pleased with the location including its proximity to the sites and the neighborhood. Fran was very kind and responsive during our stay. "
The price is €372
includes taxes & fees
7 Jul - 8 Jul
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

9.0 out of 10, Wonderful, (96)
"It's a cute house, just steps away from the beach. We had a great time enjoying all the sights around town and beach during our trip. They had everything we needed to enjoy our stay...Our host was awesome and communicated with me about everything "
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (38)
"Very cute little cottage, perfect amount of space for 2, has just about everything you'd need! Owner is helpful as well. Lots of places to eat within 15 mins"
Cozy Little Cottage on chincoteague island va.

Small cottage for those little getaways

10.0 out of 10, Exceptional, (107)
"Very cozy cottage tucked off the road great check-in experience place was clean easy parking will definitely go back again"
Small cottage for those little getaways

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (119)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Secluded Cozy Cottage in Historic Downtown

9.8 out of 10, Exceptional, (11)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is €609
includes taxes & fees
24 Jun - 25 Jun
Secluded Cozy Cottage in Historic Downtown

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

9.4 out of 10, Exceptional, (8)
"Great location, very clean and amazing staff. I highly recommend staying here."
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

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!
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 €372 and €609 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 54 cottages in Chesapeake Bay. Whether you're travelling 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!