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Compare 41 Cottages in Chesapeake Bay with updated reviews, rates, and availability.

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (375)
"Great property and a great location. "
The price is AED 1,088
AED 1,221 total
includes taxes & fees
29 May - 30 May
Key West Cottages

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

10.0 out of 10, Exceptional, (59)
"We had a lovely stay. The cottage was beautiful, very clean, and relaxing. The accommodations were top knotch and the place was very well stocked. We would definitely stay again. "
The price is AED 691
AED 898 total
includes taxes & fees
1 Jun - 2 Jun
Lovely backyard cottage with easy access to metro, shops, dining!

NEW PET FRIENDLY LISTING ALERT!!

9.0 out of 10, Wonderful, (4)
"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!!

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

9.6 out of 10, Exceptional, (43)
"This quaint treasure was amazingly friendly, very clean, perfect for a relaxing vaca. We had an awesome time and an incredible experience "
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (37)
"Exactly as listed, had a very pleasant stay and would definitely return! "
Cozy Little Cottage on chincoteague island va.

Small cottage for those little getaways

10.0 out of 10, Exceptional, (106)
"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

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

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

Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

7.0 out of 10, Good, (10)
"The Salty Sailor was an excellent, affordable, and pet friendly rental. Nice location on ridge rd next to Mr Baldys which is a must to try if you stay here. The rooms are a bit older but maintained well. I didn’t experience any of the conditions that were listed in the other reviews here. We would certainly stay here again."
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

The Hideaway Cottage

9.8 out of 10, Exceptional, (81)
"Convenient location! Exactly as advertised!"
The Hideaway Cottage

Cozy Mother-in-Law Suite

9.0 out of 10, Wonderful, (86)
"Perfect spot for a couple to relax. Property was as listed and very clean. I would definitely stay again!"
Cozy Mother-in-Law Suite

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (45)
"Very clean and in a great location. Would love to stay there again. "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

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 AED 882
AED 1,607 total
includes taxes & fees
22 Jun - 23 Jun
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)
"The hosts were awesome, the house was very comfortable, beach access was perfect. We will be back!!"
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

9.8 out of 10, Exceptional, (23)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

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

9.8 out of 10, Exceptional, (181)
"Host was amazing. Property is perfect. Will be staying here again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

9.6 out of 10, Exceptional, (118)
"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

10.0 out of 10, Exceptional, (9)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is AED 1,488
AED 2,496 total
includes taxes & fees
29 May - 30 May
Secluded Cozy Cottage in Historic Downtown

Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

10.0 out of 10, Exceptional, (117)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

Cozy Suite at the Beach

8.4 out of 10, Very Good, (58)
"Nice house"
Cozy Suite at the Beach

Pink Flamingo at the Beach

9.0 out of 10, Wonderful, (15)
"Great stay! Highly recommended!"
Pink Flamingo at the Beach
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 AED 691 and AED 1,488 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 41 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!