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Browse Select Chesapeake Bay Cottages

Our top choices for Chesapeake Bay cottages

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (431)
"Great place to stay!"
Key West Cottages

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!

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

9.6 out of 10, Exceptional, (122)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

9.6 out of 10, Exceptional, (47)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

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

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

10.0 out of 10, Exceptional, (71)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!

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

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (164)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning

7.8 out of 10, Good, (6)
"Our stay was nice. The house was clean."
Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning

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

10.0 out of 10, Exceptional, (122)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

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

10.0 out of 10, Exceptional, (51)
"As advertised, had a great time!"
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

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

Cozy Suite at the Beach

8.4 out of 10, Very good, (60)
"It was alright "
Cozy Suite at the Beach

Small cottage for those little getaways

10.0 out of 10, Exceptional, (113)
"Great place, cozy and easy to park and get around. "
Small cottage for those little getaways

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

9.0 out of 10, Wonderful, (100)
"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

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (25)
"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

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

9.8 out of 10, Exceptional, (184)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

7.0 out of 10, Good, (13)
"The Salty Sailor was an excellent, affordable, and pet friendly rental. Nice location on ridge rd next to Mr Baldys which is a must to try if you stay here. The rooms are a bit older but maintained well. I didn’t experience any of the conditions that were listed in the other reviews here. We would certainly stay here again."
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

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

9.8 out of 10, Exceptional, (26)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
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