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Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Browse Select Chesapeake Bay Cottages

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (398)
"We had wonderful stay. Everything about this resort was perfect. "
Key West Cottages
Lovely backyard cottage with easy access to metro, shops, dining!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (67)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!
Norfolk Beach Cottage Rental
Sun-loungers, beach towels

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (265)
"Great place to stay, neat little house. Property manager was very easy to chat with and very friendly. Would stay again!"
The price is £340
includes taxes & fees
4 Aug - 5 Aug
Norfolk Beach Cottage Rental
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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

9.8 out of 10, Exceptional, (182)
"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
Smart TV, DVD player, books

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!
Pool

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!
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Interior

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

9.4 out of 10, Exceptional, (131)
"Awesome two night stay! Highly recommend! "
The price is £593
includes taxes & fees
13 Jul - 14 Jul
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Pink Flamingo at the Beach
Miscellaneous

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!!
Smart TV, fireplace

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!
Fridge, microwave, oven, stovetop

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
Exterior

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

Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

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
Family and Pet-Friendly, Waterfront with Pier
Exterior

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
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Fridge, microwave, dishwasher, coffee/tea maker

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
Cozy Little Cottage on chincoteague island va.
Property grounds

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (40)
"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.
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Miscellaneous

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 £313
includes taxes & fees
29 Jul - 30 Jul
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (12)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is £555
includes taxes & fees
6 Jul - 7 Jul
Secluded Cozy Cottage in Historic Downtown
Small cottage for those little getaways
Exterior

Small cottage for those little getaways

10.0 out of 10, Exceptional, (109)
"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
Marina

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

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!
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 £313 and £593 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!