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Check prices for these dates

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1 Aug - 3 Aug
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8 Aug - 10 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Cottages in Chesapeake Bay and around

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (408)
"We had wonderful stay. Everything about this resort was perfect. "
Key West Cottages
The Hideaway Cottage
Beach nearby

The Hideaway Cottage

9.8 out of 10, Exceptional, (87)
"Convenient location! Exactly as advertised!"
The Hideaway Cottage
Cozy Little Cottage on chincoteague island va.
Property grounds

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (42)
"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
Fridge, microwave, oven, stovetop

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (270)
"We enjoyed our stay. The house was right across the street from a beautiful beach! The house was clean and check in was easy!"
The price is €384
includes taxes & fees
26 Aug - 27 Aug
Norfolk Beach Cottage Rental
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

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!
Pool

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!
Exterior

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

10.0 out of 10, Exceptional, (92)
"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
Interior

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

9.4 out of 10, Exceptional, (132)
"Awesome two night stay! Highly recommend! "
The price is €710
includes taxes & fees
25 Aug - 26 Aug
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Pink Flamingo at the Beach
Property grounds

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

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

9.0 out of 10, Wonderful, (98)
"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
Outdoor dining

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
Exterior

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!
Fridge, microwave, oven, stovetop

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
Property grounds

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
On the beach

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
Exterior

Small cottage for those little getaways

10.0 out of 10, Exceptional, (110)
"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
Interior

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (84)
"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!
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!
Treetop Rustic Beach Front 2 Bedroom Apartment
Exterior

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (23)
"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...
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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Top Chesapeake Bay Hotel Reviews

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

10/10 Excellent
"Enjoyed our stay. Resort upgraded us to two bedroom due to availability but it was just the two of us. Trouble with ice maker and we called and the response to correct it was the fastest I’ve ever had. Resort also brought us a bag of ice to use while our refrigerator was creating new ice. We would stay here again without a doubt. All we wanted to do locally was nearby."
Cynthia 3-night trip
Posted 14 hours ago
Hilton Vacation Club The Historic Powhatan Williamsburg

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
Rates for cottages in Chesapeake Bay range between €384 and €710 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!