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Featured Cottages in Chesapeake Bay and around

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (455)
"Great place to stay!"
Key West Cottages

NEW PET FRIENDLY LISTING ALERT!!

9.2 out of 10, Wonderful, (18)
"Very clean, spacious and perfect for a stay with my girlfriend and two dogs! Definitely recommend!"
NEW PET FRIENDLY LISTING ALERT!!

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

10.0 out of 10, Exceptional, (74)
"Wonderful stay, truly a gem. "
Lovely backyard cottage with easy access to metro, shops, dining!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (257)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (120)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

10.0 out of 10, Exceptional, (123)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

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

9.6 out of 10, Exceptional, (14)
"3 night stay for our anniversary, beautiful view had a relaxing time! "
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

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

9.6 out of 10, Exceptional, (51)
"Very nice and clean and directly at the water. Well equipped and beautiful view and close to everything. Perfect place for a peaceful getaway to explore beautiful Chincoteague. "
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (48)
"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.

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

10.0 out of 10, Exceptional, (16)
"We had a very comfortable stay here. The cottage is a convenient walking distance to restaurants and shops. It came stocked with all the necessities. Very satisfied. "
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

Cozy Mother-in-Law Suite

8.8 out of 10, Excellent, (89)
"Small unit to the rear of rental property. Could not stay in property for length of planned trip."
Cozy Mother-in-Law Suite

Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

8.6 out of 10, Excellent, (14)
"Had a great time, very convenient beach access. Only complaint is there wasn’t a washer and dryer like the listing stated. Would definitely rent again."
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

Cozy Bay Cottage private backyard blocks from beach!

9.0 out of 10, Wonderful, (42)
"We showed up and found a clean and cool spot to stay the night. The beach access is only a 5 minute walk to the bay. This was spectacular! We were also only 1 mile from Jessie's Taquaria which is thr Mexican food in Norfolk. Overall this property checked all our boxes."
The price is €375
includes taxes & fees
24 Sept - 25 Sept
Cozy Bay Cottage private backyard blocks from beach!

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (36)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (26)
"Repeat guest.. stayed in another unit previously *loft property.Property is very close to the beach, can walk into the sand from the property. Pet friendly is a plus.. lots of doggos on the beach.Property has the basics.. minimal items in unit, so you need to bring quite a bit of things to make your trip complete. Owners have several units, so amenities are shared. Husband and I used the charcoal grill and set by the firepit in the sand. Not sure id stay in this particular unit again, but id...
The price is €238
includes taxes & fees
1 Oct - 2 Oct
Treetop Rustic Beach Front 2 Bedroom Apartment

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (273)
"To honor my elderly mothers request to go to the beach for a weekend, I looked for a small house that wasn't too expensive and where everything was on one floor. The cottage met our requirements. The cottage was clean, had ample towels, and the beds were comfortable. The check-in and out was very easy. The owners were very kind and pleasant to work with. We had a wonderful visit."
The price is €351
includes taxes & fees
24 Sept - 25 Sept
Norfolk Beach Cottage Rental

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

9.8 out of 10, Exceptional, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks

9.8 out of 10, Exceptional, (14)
"It was a great stay! We really enjoyed the cabin! The area was nice and everyone was very friendly. We would definitely stay again!"
The price is €235
includes taxes & fees
24 Sept - 25 Sept
Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks

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

7.0 out of 10, Good, (13)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Enjoyable and relaxing"
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
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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Top Chesapeake Bay Hotel Reviews

Find out more about Chesapeake Bay

Find out more about Chesapeake Bay

Chesapeake Bay Cottages information

Number of reviews
1,874
Accommodation
80 Cottages
Lowest Price
€235
Highest Price
€375

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
Rates for cottages in Chesapeake Bay range between €235 and €375 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 80 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!

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