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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, (338)
"Even though we saw quite a few guests, we never heard a sound. the cottage was neat & clean. The bed was very comfortable. The staff was friendly and helpful. Although a little too chilly to sit on the waterfront deck, it was a lovely tranquil view. "
The price is AED 493
AED 553 total
includes taxes & fees
31 Mar - 1 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, (44)
"Exceeded expectations :) would come again and definitely recommend to friends or family!"
The price is AED 661
AED 860 total
includes taxes & fees
9 Apr - 10 Apr
Lovely backyard cottage with easy access to metro, shops, dining!

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (255)
" 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 657
AED 1,354 total
includes taxes & fees
31 Mar - 1 Apr
Norfolk Beach Cottage Rental

SeaLaVie!!!

9.8 out of 10, Exceptional, (39)
"Wonderful town, friendly people, good food, amazing Refuge with horses, wildlife. We just absolutely adore Chincoteague. Cottage was cozy, comfortable, good location. Dogs loved the nearby fog park. Hostess was friendly, very helpful with local events. Just a wonderful time"
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, (128)
"This house is great for small family with dogs . I had my 2 daughters , wife and 2 dogs and the house was perfect. Great condition, location, and the house Manager was great ! Always there if I had any questions and really made sure I and my family felt like home and had everything we needed . I would recommend this place to anyone and will definitely be happy to book this property in the future"
The price is AED 973
AED 1,207 total
includes taxes & fees
31 Mar - 1 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, (175)
"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, (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, (14)
"Do not have a lot of experience with Air B&B's , you made my trip wonderful. The house was very clean and updated. For a business trip. it was a great place to stay because of the two floors, we were able to break off into our own spaces. Wonderful experience from scheduling to leaving. Would highly recommend. "
The price is AED 735
AED 1,423 total
includes taxes & fees
13 Apr - 14 Apr
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 1,329 total
includes taxes & fees
2 Apr - 3 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, (117)
"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

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, (95)
"The place was in a great location and having everything on one floor was a huge benefit as one of the guests is disabled. The place could use some updates but other than that it was nice! The owner was very responsive to our needs and got right back to us if we had any question! If we ever go back, we would consider this place again!"
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Cozy Mother-in-Law Suite

9.0 out of 10, Wonderful, (85)
"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, (2362)
"The downstairs restaurant is delicious and friendly with live jazz on the Tuesday we stayed "
The price is AED 526
AED 610 total
includes taxes & fees
18 Apr - 19 Apr
Glover Park - Georgetown

The Churchill Hotel near Embassy Row

3.5 star property
8.8 out of 10, Excellent, (1682)
"Excellent Location!"
The price is AED 413
AED 586 total
includes taxes & fees
20 Apr - 21 Apr
The Churchill Hotel near Embassy Row

The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1628)
"Loved our stay in Foggy Bottom! "
The price is AED 637
AED 738 total
includes taxes & fees
6 Apr - 7 Apr
The River Inn
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.

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
Rates for cottages in Chesapeake Bay range between AED 493 and AED 973 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 43 cottages in Chesapeake Bay. Whether you’re traveling 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!
How can I find cheap cottages in Chesapeake Bay?
With Expedia’s user-friendly filter tool, scoring cheap cottages in Chesapeake Bay couldn’t be simpler. To discover accommodations that’ll make your wallet smile, fine-tune your search results by amenities, star rating and budget.