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Compare 43 Cottages in Chesapeake Bay with updated reviews, rates, and availability.

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (354)
"We loved it! Clean, convenient, everything we needed. "
The price is AED 658
AED 739 total
includes taxes & fees
23 Apr - 24 Apr
Key West Cottages

Waterfront Willoughby Oasis

10.0 out of 10, Exceptional, (1)
"I just want to thank our host again and again. The communication was amazing and Audra was so accommodating for our last minute booking. We had to rush into town due to a family member’s death, but the house’s picture perfect location makes us want to go back under happier circumstances. "
Waterfront Willoughby Oasis

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

10.0 out of 10, Exceptional, (47)
"This adorable little cottage was in a beautiful neighborhood and tucked away in a magical garden. The inside was immaculate and stylish. My kids and I all loved it and it was so close to D.C. I would absolutely stay here again!"
The price is AED 680
AED 890 total
includes taxes & fees
5 May - 6 May
Lovely backyard cottage with easy access to metro, shops, dining!

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (258)
" The house is super cute and conveniently located just a short drive from the ODU campus and within walking distance to a beautiful beach. there are plenty of shopping and food, places nearby, making this a great spot for a weekend getaway. The host were also incredibly helpful and friendly! Would recommend! "
The price is AED 518
AED 1,177 total
includes taxes & fees
28 Apr - 29 Apr
Norfolk Beach Cottage Rental

SeaLaVie!!!

9.8 out of 10, Exceptional, (40)
"Great location "
SeaLaVie!!!

The Hideaway Cottage

9.8 out of 10, Exceptional, (79)
"Has what you need. It is cozy. Close to town and the beach. Third time staying here. Love it. "
The Hideaway Cottage

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

7.0 out of 10, Good, (10)
"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

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

9.6 out of 10, Exceptional, (130)
"Large kitchen and overall convenient location. Toilet paper holder in bathroom was missing so we had to chase the roll a few times after it fell off the back of the toilet. I'm guessing they can fix that easily. "
The price is AED 961
AED 1,193 total
includes taxes & fees
23 Apr - 24 Apr
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

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

9.8 out of 10, Exceptional, (179)
"I have stayed in almost every hotel and Vrbo is St Michael’s and this is my favorite house. The screen porch is a dream and there is plenty of space for my family. Just dreamy."
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, (115)
"Thank you so much for a wonderful stay! We really enjoyed our time at your beautiful house. Everything was well kept, very clean, very organized. You can tell Armando really keeps up with the house and makes sure it is welcoming to guests. Very close to Williamsburg, Jamestown, etc. "
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

10.0 out of 10, Exceptional, (17)
"Check in process was seamless and easy. The owner communicated all the info ahead of time, AND was available and responsive to all our silly questions we had regarding using the thermostat and such. Very easy and friendly communication. The house and property all around is very clean, literally no dust or any grime whatsoever. At the same time, there was no cleaning product smell, which was a huge relief for us. Lots of toilet paper, paper towels, napkins etc. Thank you that I did not have to...
The price is AED 882
AED 1,611 total
includes taxes & fees
4 May - 5 May
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

Cozy Bay Cottage private backyard blocks from beach!

8.8 out of 10, Excellent, (35)
"The house was so cute and well taken care of. Plenty of space for a larger group and very close to the beach. I would definitely recommend this house and stay again! Richard was so helpful and communicative. Overall great experience! "
The price is AED 635
AED 1,312 total
includes taxes & fees
27 Apr - 28 Apr
Cozy Bay Cottage private backyard blocks from beach!

Small cottage for those little getaways

10.0 out of 10, Exceptional, (105)
"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

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

9.6 out of 10, Exceptional, (118)
"Shower was disappointing. Hard to get in and out."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Cozy Little Cottage on chincoteague island va.

9.4 out of 10, Exceptional, (36)
"The cottage is as described. There is no stove but it truly didn’t matter. Bed is very compfy. Shower is clean and hot. Quit neighborhood. The screened in porch is the best! Coffee and reading in the rockers. The cottage is close to everything !Thank you Don. We loved our stay."
Cozy Little Cottage on chincoteague island va.

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

9.6 out of 10, Exceptional, (43)
"This quaint treasure was amazingly friendly, very clean, perfect for a relaxing vaca. We had an awesome time and an incredible experience "
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Mermaid's and Mutts Retreat

9.0 out of 10, Wonderful, (31)
"Very cute old house right on the beach but it needs some serious work.. if you open certain cabinet doors in the kitchen it hits the ceiling fan, they had the dryer door taped shut but of course it kept popping open so the dryer is unusable, stains on the carpets and wood floors, missing outlet covers, the back deck is seriously unsafe you feel it sway with any small movement and it needs a good deep clean the ac filter covers are caked in dust and they’re Cobb webs in a lot of the corners....
Mermaid's and Mutts Retreat

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

Cozy Mother-in-Law Suite

9.0 out of 10, Wonderful, (86)
"Perfect spot for a couple to relax. Property was as listed and very clean. I would definitely stay again!"
Cozy Mother-in-Law Suite
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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Other property types in Chesapeake Bay

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2394)
"We had a lovely stay at the Glover Park Hotel in Georgetown. While the building itself is older and the hotel isn’t modern or luxurious, it has a certain charm and character that makes it feel cozy and inviting. The location is fantastic — in a quiet part of Georgetown with easy access to the waterfront, restaurants, and great shopping. We found it very convenient to get around. The hotel was clean, well-kept, and a great value for the price. It’s definitely a solid 3-star stay — nothing...
The price is AED 804
AED 933 total
includes taxes & fees
1 May - 2 May
Glover Park - Georgetown

The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1656)
"Staff was very friendly"
The price is AED 621
AED 720 total
includes taxes & fees
27 Apr - 28 Apr
The River Inn

The Churchill Hotel near Embassy Row

3.5 star property
8.8 out of 10, Excellent, (1710)
"Location is good and area is safe"
The price is AED 1,402
AED 1,736 total
includes taxes & fees
5 May - 6 May
The Churchill Hotel near Embassy Row
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.