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Browse Select Chesapeake Bay Cottages

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (414)
"Key West Cottages is absolutely wonderful!"
The price is CA $276
CA $311 total
includes taxes & fees
Sep 2 - Sep 3
Key West Cottages

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.

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

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 CA $250
CA $575 total
includes taxes & fees
Sep 3 - Sep 4
Norfolk Beach Cottage Rental

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!

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!

10.0 out of 10, Exceptional, (93)
"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!

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

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

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

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

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

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

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

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

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!

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!

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

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!

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