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Check prices for these dates

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15 Aug - 17 Aug
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22 Aug - 24 Aug
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5 Sept - 7 Sept
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3 Oct - 5 Oct

Featured Cottages in Chesapeake Bay and around

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, (415)
"Key West Cottages is absolutely wonderful!"
Key West Cottages
The Hideaway Cottage
Relax on the beach with two comfortable chairs, perfect for taking in the ocean views.

The Hideaway Cottage

9.8 out of 10, Exceptional, (88)
"Convenient location! Exactly as advertised!"
The Hideaway Cottage
Cozy Little Cottage on chincoteague island va.
Escape to a serene cabin surrounded by nature, with a porch and a tranquil lawn.

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (44)
"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.
Norfolk Beach Cottage Rental
Stroll up to this charming home with a welcoming porch, mailbox, and white picket fence.

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (271)
"We enjoyed our stay. The house was right across the street from a beautiful beach! The house was clean and check in was easy!"
Norfolk Beach Cottage Rental
Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg
Traditional two-story home with a central chimney and wrap-around porch, set amidst well-mainters landscaping.

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

8.0 out of 10, Very good, (1)
"This listing says cottage but it's an apartment. Be ready to go up stairs to get into it. The kitchen is small but fine. Everything works, but it's not especially well equipped for cooking. The coffee maker does not work. Our checkin was delayed for about 40 minutes when we arrived and we had no where to stay while waiting for our apartment. Wi Fi was very weak in the apartment and TV is like a hotel where there are certain channels available but no way to sign in to your own streaming accounts....
Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Relax by the serene waterfront, where kayaks line the shore and Adirondack chairs invite you to unwind.

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

9.4 out of 10, Exceptional, (10)
"Great location, very clean and amazing staff. I highly recommend staying here."
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Pink Flamingo at the Beach
A charming single-story building with a white door and decorative iron grilles adorns the facade.

Pink Flamingo at the Beach

8.6 out of 10, Excellent, (16)
"older place but very nice and close to the beach"
Pink Flamingo at the Beach
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Enjoy a serene beach experience with access to the ocean.

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

9.0 out of 10, Wonderful, (99)
"If you’re looking for a place for you to have a safe space with your family, young or old, with all the amenities that you would want from your own home this is it. If you’re a veteran, there’s multitude of bases nearby with commissary’s to get groceries for the week to help the budget. "
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Enjoy a patio surrounded by lush trees and a well-manicured lawn.

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

9.8 out of 10, Exceptional, (184)
"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
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Cozy home with a front porch and well-manicured yard.

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

10.0 out of 10, Exceptional, (121)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Small cottage for those little getaways
Situated in a residential area, this cabin offers a peaceful retreat surrounded by mature trees and a grassy yard with ocean views.

Small cottage for those little getaways

10.0 out of 10, Exceptional, (110)
"Quiet, romantic getaway in a pretty setting. The cottage is lovely with nice furnishings. I loved the screened in porch."
Small cottage for those little getaways
Lovely backyard cottage with easy access to metro, shops, dining!
Relax on the deck or patio, surrounded by a beautifully maintained garden and a wooden fence.

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

10.0 out of 10, Exceptional, (68)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
A simple, single-story building with two entrance doors and a grassy surroundings.

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

9.6 out of 10, Exceptional, (25)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
Sandy Mutts at the Beach
Cozy single-story house with a front porch and grassy lawn.

Sandy Mutts at the Beach

8.0 out of 10, Very good, (14)
"It was a wonderful stay and our host was wonderful to work with. We will be back soon! "
Sandy Mutts at the Beach
Cozy Mother-in-Law Suite
Traditional front entrance with decorative accents and secure design.

Cozy Mother-in-Law Suite

9.0 out of 10, Wonderful, (88)
"Small unit to the rear of rental property. Could not stay in property for length of planned trip."
Cozy Mother-in-Law Suite
Shackeau East - Magnificent Views!
Relax in a serene outdoor space with a view of the water, featuring a wicker seating area and large windows.

Shackeau East - Magnificent Views!

9.8 out of 10, Exceptional, (14)
"great spot close to park "
Shackeau East - Magnificent Views!
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
A small, single-story cabin with a gabled roof, featuring a front door and a porch area.

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

10.0 out of 10, Exceptional, (12)
"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!
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Beach nearby

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

8.0 out of 10, Very good, (4)
"The location is great for a family with pets. The check in and out process was simple and the host was responsive. No complaints! "
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Guest house with a covered porch, surrounded by a white picket fence and landscaped grounds.

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

10.0 out of 10, Exceptional, (51)
"Very clean and in a great location. Would love to stay there again. "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
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

Omni Shoreham Hotel

Omni Shoreham Hotel

10/10 Excellent
"Very well located, has a lot of food options, really enjoyed the pool. This hotel is highly recommended "
Melano 3-night trip
Posted 7 hours ago
Omni Shoreham Hotel

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 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!