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Check prices for these dates

Next weekend
25 July - 27 July
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Chesapeake Bay

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, (404)
"We had wonderful stay. Everything about this resort was perfect. "
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, (86)
"Convenient location! Exactly as advertised!"
The Hideaway Cottage
Cozy Little Cottage on chincoteague island va.
Guests can enjoy a barbecue in the garden.

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.
Norfolk Beach Cottage Rental
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and dishwasher.

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (268)
"Great place to stay, neat little house. Property manager was very easy to chat with and very friendly. Would stay again!"
The price is AU$681
includes taxes & fees
4 Aug - 5 Aug
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, (9)
"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, (91)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Relax on the serene porch with a view of lush green surroundings, featuring two comfortable chairs and an entrance.

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

9.4 out of 10, Exceptional, (131)
"Awesome two night stay! Highly recommend! "
The price is AU$1,096
includes taxes & fees
16 July - 17 July
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Pink Flamingo at the Beach
Walk along the beachside boardwalk, lined with metal railings and wooden planks, offering a safe path to the ocean.

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
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Walk along the beachside boardwalk surrounded by lush greenery and enjoy the serene atmosphere.

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
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

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

9.8 out of 10, Exceptional, (183)
"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
Manor and Mutts #1 (4-Bedroom Cottage) - Pets Allowed by RedAwning
Terrace/patio

Manor and Mutts #1 (4-Bedroom Cottage) - Pets Allowed by RedAwning

8.0 out of 10, Very good, (10)
"Great location on water. Dog had a great time."
Manor and Mutts #1 (4-Bedroom Cottage) - Pets Allowed by RedAwning
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Stunning two-story home with a central entrance, white porch, and beautifully maintained garden.

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

10.0 out of 10, Exceptional, (120)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Lovely backyard cottage with easy access to metro, shops, dining!
Enjoy cooking in this well-lit kitchen with a sleek island and stainless steel appliances.

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!
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
Escape to a serene natural oasis with a tranquil grassy area and a picturesque wooded backdrop.

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

9.6 out of 10, Exceptional, (24)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
Sandy Mutts at the Beach
Relax in comfort with three beach chairs along the fence, overlooking the serene beach and grassy area.

Sandy Mutts at the Beach

8.0 out of 10, Very good, (13)
"It was a wonderful stay and our host was wonderful to work with. We will be back soon! "
Sandy Mutts at the Beach
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, (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
Perfect location for USNA Commissioning Week
Relax in this open-plan living area featuring a central island, dining space, and comfortable seating.

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (83)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Enjoy cooking and dining in this well-organized kitchen with a central island and dining area.

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!
Treetop Rustic Beach Front 2 Bedroom Apartment
Explore a charming multi-level structure surrounded by lush trees, featuring a balcony with a railing and windows with curtains.

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (23)
"Wonderful owners with phenomenal communication. They were very patient and super responsive to messages. They went above and beyond to make us comfortable. Property had everything we needed and more and was steps from the ocean. The beach itself was private and not crowded at all. This was our 2nd time staying and will definitely not be our last."
Treetop Rustic Beach Front 2 Bedroom Apartment
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?
You'll pay between AU$681 and AU$1,096 per night for cottages in Chesapeake Bay. No matter your budget, an excellent stay is only clicks away on Expedia. This price was 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?
Browse through our 54 cottages in Chesapeake Bay and then choose your favourite. Whether you're embarking on a family holiday or a break with pals, your ideal stay is just clicks away with Expedia.
What is there to do in Chesapeake Bay near my cottage?
Whether you're interested in history, food, shopping or sightseeing, Chesapeake Bay is one place you'll never get bored! The awesome city of Washington has plenty of things to do and see, including National Mall, Smithsonian Institution and National Museum of African American History and Culture. If you're headed to Baltimore, National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum are must-do's.