Search Cottages in Chesapeake Bay

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 22 Cottages in Chesapeake Bay with updated reviews, rates, and availability.

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (326)
"Very nice cottages "
The price is AED 443
AED 498 total
includes taxes & fees
25 Feb - 26 Feb
Key West Cottages

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (251)
"Stayed here with a few friends to celebrate my birthday, it was a great time, the house is cozy and clean, getting there and parking is easy and the extra amenities provided were a nice addition as well."
The price is AED 731
AED 1,430 total
includes taxes & fees
25 Feb - 26 Feb
Norfolk Beach Cottage Rental

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

9.8 out of 10, Exceptional, (173)
"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

SeaLaVie!!!

9.8 out of 10, Exceptional, (38)
"Loved it. It was clean and just a lovely quaint cabin. Just enough for us to enjoy each others company. Would recommend this place to my other friends and family. Thank you to the wonderful host for a beautiful Christmas with our kids! "
SeaLaVie!!!

Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes

10.0 out of 10, Exceptional, (11)
"Cozy and clean cottage with all the amenities. Close to everything!"
Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes

Cozy Suite at the Beach

8.4 out of 10, Very Good, (56)
"The manager made a mistake. He owned it and gave us a better place. The parking could have been better. It served our purposes well. It was quiet and private. My husband fished every morning. Our first choice would not have been as nice."
Cozy Suite at the Beach

Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath

8.6 out of 10, Excellent, (43)
"Wonderful accommodations. Thank you for a great stay!"
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath

Shackeau East - Magnificent Views!

9.8 out of 10, Exceptional, (8)
"Three nights, me and my hubby. Found the property easily. Clean. Decorated and comfortable. Disappointed that we didn’t have access to a working fireplace. Would have been nice on a cool windy evening but otherwise nice n warm. Loved the huge front deck wrapped myself in a quilt and read in the sunshine enjoying the peace and water view. "
Shackeau East - Magnificent Views!

Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!!!

10.0 out of 10, Exceptional, (109)
"The cottage was perfect and the hosts are great communicators. It was cozy and all updated, my kids loved it and asked when we're going back. "
Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!!!

2BR SNUG HARBOR 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 SNUG HARBOR Waterfront Cottage with the Most Spectacular View of lighthouse

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 755
AED 919 total
includes taxes & fees
25 Feb - 26 Feb
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

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

10.0 out of 10, Exceptional, (114)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

Mermaid's and Mutts Retreat

9.0 out of 10, Wonderful, (30)
"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

Pink Flamingo at the Beach

9.0 out of 10, Wonderful, (12)
"Great stay! Highly recommended!"
Pink Flamingo at the Beach

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (78)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!

Beach Lovers Delight (3-Bedroom Cottage) - Pets Allowed by RedAwning

10.0 out of 10, Exceptional, (2)
"The property is conveniently located. It’s directly on the beach, although there are dunes that obstruct the beach view. But, the dunes are also beautiful! It’s a very roomy house with lots of space, and little cozy nooks. It’s exactly as advertised. Not a brand new house, has some age related quirks, but it’s clean and not a cookie cutter house which was refreshing to us. Will book again!"
Beach Lovers Delight (3-Bedroom Cottage) - Pets Allowed by RedAwning

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.

Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning

9.6 out of 10, Exceptional, (4)
"This is a very spacious house for four and possibly for more a short walk from the beach, through some trees and directly to the water. Despite the highway in view, it was very quiet and was comfortable for our weekend stay. Despite the somewhat spare decor and slightly random kitchen, we had everything we needed. While it is an older house, there were minimal quirks and the location is excellent."
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning

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

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (157)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
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.
Don't see what you're looking for?
See all available properties in Chesapeake Bay
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesapeake Bay

The Melrose Georgetown Hotel

4.0 star property
8.8 out of 10, Excellent, (2088)
"Incredibly well located at the heart of DC, great amenities and staff."
The price is AED 526
AED 733 total
includes taxes & fees
7 Mar - 8 Mar
The Melrose Georgetown Hotel

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2326)
" Over the hotel is fine. But the most i' d like its Dining area. So tasty food. The employees in there are so friendly. "
The price is AED 603
AED 700 total
includes taxes & fees
25 Feb - 26 Feb
Glover Park - Georgetown

ARC HOTEL Washington DC, Georgetown

3.0 star property
8.2 out of 10, Very Good, (2219)
"The coffee machine downstairs didn't always work and the coffee didn't really taste good and the water dispenser inside the gym also didn't work all the time. "
The price is AED 474
AED 549 total
includes taxes & fees
27 Feb - 28 Feb
ARC HOTEL Washington DC, Georgetown
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?
You’ll pay between AED 443 and AED 755 per night for cottages in Chesapeake Bay. No matter your budget, a wonderful stay is just a click or two away on Expedia. 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?
Chesapeake Bay has 22 cottages to pick from. Enter your travel dates and destination and start planning your ideal vacation today.
Why book your cottage in Chesapeake Bay with Expedia?
We think a getaway should be stress-free, so if you’re searching for cottages in Chesapeake Bay at a nice price, Expedia has got you covered. Keep costs down and opt for a cheap option surrounded by nature, or splurge on a luxury cottage to spoil your favorite people.
How can I find cheap cottages in Chesapeake Bay?
With Expedia’s user-friendly filter tool, comparing cheap cottages in Chesapeake Bay is a snap. To view properties that’ll make your wallet happy, refine your search results by amenities, budget and star rating.