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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 28 Cottages in Chesapeake Bay with updated reviews, rates, and availability.

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (319)
"I stayed in the Key Lime Cottage with 2 friends. The cottage is beautiful, clean, and very well stocked. There are two gas grills and a firepit overlooking the water that guests could use. The pool is huge and looked very nice. Loved this place!! Would definitely return!! "
The price is AED 443
AED 498 total
includes taxes & fees
9 Feb - 10 Feb
Key West Cottages
Norfolk Beach Cottage Rental
Front of house

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (249)
"This property is in a great location for beach access and provided exactly what I needed for a holiday link up with my adult children. The homeowners were exceptional in their customer service, providing an introduction and being prompt and courteous to any questions. As a first time renter, this was appreciated."
The price is AED 731
AED 1,430 total
includes taxes & fees
25 Jan - 26 Jan
Norfolk Beach Cottage Rental
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
SeaLaVie!!!
Exterior

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!!!
Cozy 3-bedroom cottage - new HOT TUB, dogs OK, fenced yard
Welcome to Wayland Beach Cottage!

Cozy 3-bedroom cottage - new HOT TUB, dogs OK, fenced yard

10.0 out of 10, Exceptional, (28)
"Property was clean- well taken care of. "
Cozy 3-bedroom cottage - new HOT TUB, dogs OK, fenced yard
Cozy Bay Cottage private backyard blocks from beach!
Beach

Cozy Bay Cottage private backyard blocks from beach!

8.8 out of 10, Excellent, (33)
"Nicely appointed. Super close to beach. Has coffee maker but no supplies, so be sure to bring filters, coffee, and cream/sugar. Good communication with owner when we had questions."
The price is AED 635
AED 1,312 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Bay Cottage private backyard blocks from beach!
Cozy Suite at the Beach
Boardwalk to the Beach

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
Shackeau East - Magnificent Views!
Popular 'Shackeau East' is not part of the Seaside Vacations' Family!

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

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

8.4 out of 10, Very Good, (42)
"Wonderful accommodations. Thank you for a great stay!"
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Cozy Little Cottage on chincoteague island va.
Exterior detail

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 SNUG HARBOR Waterfront Cottage with the Most Spectacular View of lighthouse
Pool

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
The Hideaway Cottage
Outdoor dining

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
Small cottage for those little getaways
Exterior

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
Beach Lovers Delight (3-Bedroom Cottage) - Pets Allowed by RedAwning
Architecture,Building,House,Roof,Cottage

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
Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (77)
"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!
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning
"Patio","Deck","Flagstone","Pottery"

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
Old Time Ocean View Cottage
Exterior

Old Time Ocean View Cottage

Old Time Ocean View Cottage
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House

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

9.6 out of 10, Exceptional, (116)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private
Property grounds

Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

8.8 out of 10, Excellent, (13)
"We left the property an hour after arrival due to the tremendous smoking smell in the property, the dirty and stained couches (one smells of urine), and busted window screens which kept us from being able to open windows and air out the duplex. For minimal investment in screens and going to a thrift store for clean sofas, this property could be fine, smoking smell aside. The other side of the duplex, I suspect is lived in semi permanently as when I contacted the owner about the smoking smell,...
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private
Treetop Rustic Beach Front 2 Bedroom Apartment
Beach

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (23)
"The kitchen was ok…when we walked in the living room the outlet was pushed into the wall…the walls seems liked they were patched up but never painted…the floors have soft spots and uneven in almost every room…garbage behind the radiators that has been there for years….the master bed was shimmed with cut pieces of 2x4’s…huge crack in the corner wall leading to the bathroom…the bathroom sink is just above knee high. The shower …if you’re over 5’2” you will be crouching or squatting if you’re 6’2”...
The price is AED 143
AED 721 total
includes taxes & fees
27 Jan - 28 Jan
Treetop Rustic Beach Front 2 Bedroom Apartment
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

ARC HOTEL Washington DC, Georgetown
Exterior

ARC HOTEL Washington DC, Georgetown

3.0 star property
8.2 out of 10, Very Good, (2176)
"Excellent stay and the staff was very helpful."
The price is AED 403
AED 467 total
includes taxes & fees
26 Jan - 27 Jan
ARC HOTEL Washington DC, Georgetown
Glover Park - Georgetown
Terrace/patio

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2297)
"I had a wonderful stay at this hotel! The boutique ambiance was charming and added a unique touch to my visit. The room was spacious, providing plenty of comfort, and the beds were incredibly cozy, ensuring a restful night’s sleep. The location was perfect, making it easy to explore the surrounding area with everything conveniently nearby. I also enjoyed dining at the hotel’s restaurant, which offered delicious food and excellent service. Overall, this hotel exceeded my expectations, and I would...
The price is AED 590
AED 684 total
includes taxes & fees
26 Jan - 27 Jan
Glover Park - Georgetown
The Dupont Circle Hotel
Lobby lounge

The Dupont Circle Hotel

4.5 star property
9.4 out of 10, Exceptional, (1486)
"I love the Dupont Circle Hotel, and this is the only place I stay while in DC. Their furniture on my latest stay was looking a little worse for wear, but I think a small spruce up will bring it back to its former glory. Maybe update the carpet and the furniture facings. But the amenities, restaurants, and room service are too notch. The street facing rooms can get a bit noisy. "
The price is AED 988
AED 1,146 total
includes taxes & fees
25 Jan - 26 Jan
The Dupont Circle Hotel
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 143 and AED 731 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 28 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.