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Compare 31 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, (304)
"Was there for business but will go back for pleasure, this place is amazing "
The price is SAR 453
SAR 509 total
includes taxes & fees
5 Jan - 6 January 2025
Key West Cottages
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, (76)
"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!
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior detail

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

10.0 out of 10, Exceptional, (81)
"A very nice and well-maintained cottage in the Cape St. Clair neighborhood where family members live. The owners have done a great job of provisioning the cottage both inside and outside, for recreational opportunities and enjoyment (barbecuing and relaxing). The backyard is very large and great for games provided with the property, like corn hole. There is also a hot tub. The owners have found the right balance for being responsive when you need them, while leaving you in peace otherwise....
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
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.
Cozy Bay Cottage private backyard blocks from beach!
Beach

Cozy Bay Cottage private backyard blocks from beach!

8.8 out of 10, Excellent, (32)
"The house is as promised - in a charming neighborhood just a short walk from the beach. The host supplied everything for a comfortable beach retreat."
Cozy Bay Cottage private backyard blocks from beach!
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, (40)
"Loved the ease of access we had to everything. Place was as described on website. Will be recommending. "
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
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 SAR 748
SAR 1,467 total
includes taxes & fees
23 Dec - 24 Dec
Norfolk Beach Cottage Rental
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 - fenced yard, 4 TVs, dogs OK, W/D
Welcome to Wayland Beach Cottage!

Cozy 3-bedroom cottage - fenced yard, 4 TVs, dogs OK, W/D

10.0 out of 10, Exceptional, (28)
"Property was clean- well taken care of. "
Cozy 3-bedroom cottage - fenced yard, 4 TVs, dogs OK, W/D
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
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."
The price is SAR 147
SAR 651 total
includes taxes & fees
23 Dec - 24 Dec
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!
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Exterior

Island Breeze Cottage w/ screened porch. Water view! Quiet location!

9.8 out of 10, Exceptional, (275)
"Clean and quiet. Efficient use of space"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
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)
"Wonderful property and great location. Would love to stay in cabin 5 again. Had everything we needed. Management was friendly and always available."
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
Beachfront paradise, relaxed, pet friendly
Livingroom

Beachfront paradise, relaxed, pet friendly

9.6 out of 10, Exceptional, (18)
"Everything was great . Steps to the ocean . Fairly secluded . Many restaurants and stores nearby ."
Beachfront paradise, relaxed, pet friendly
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
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
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

The Dupont Circle Hotel
Lobby lounge

The Dupont Circle Hotel

4.5 star property
9.4 out of 10, Exceptional, (1464)
"My favorite place to stay in DC. The staff are always amazing. So friendly, professional and attentive. I did experience a few negatives this time. No room upgrade was offered and was supposed to be. I also had to ask about my Expedia VIP bar/restaurant credit. Slow on getting ice; wish I could get my own. One beside lamp didn’t work. But I will still be back! Can’t beat the high end service and location. "
The price is SAR 1,011
SAR 1,172 total
includes taxes & fees
23 Dec - 24 Dec
The Dupont Circle Hotel
Glover Park - Georgetown
Terrace/patio

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2274)
"I would return "
The price is SAR 478
SAR 554 total
includes taxes & fees
30 Dec - 31 Dec
Glover Park - Georgetown
ARC HOTEL Washington DC, Georgetown
Exterior

ARC HOTEL Washington DC, Georgetown

3.0 star property
8.2 out of 10, Very Good, (2134)
"The stay was nice. Despite the fact it wasn’t in Georgetown, it was still accessible especially for people who don’t drive or can’t afford ride shares. The metro is within walking distance. I wasn’t aware of a deposit. And there’s no microwave. These are minor things but I enjoyed my stay overall "
The price is SAR 364
SAR 422 total
includes taxes & fees
23 Dec - 24 Dec
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 SAR 147 and SAR 748 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 31 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.