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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 39 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, (293)
"I love how quiet and relaxing the property was this time of year. Amazing views. I look forward to returning soon!"
The price is SAR 453
SAR 509 total
includes taxes & fees
1 Dec - 2 Dec
Key West Cottages
Norfolk Beach Cottage Rental
Front of house
Norfolk Beach Cottage Rental
9.0 out of 10, Wonderful, (247)
"I stayed here with a couple friends for my birthday party, and we all loved this place!! It was not as small as they warned us to be, and I would say it’s the perfect place to have a party with a few friends. I would 100% stay and have a party here again :) I have to thank the owner’s for fast and efficient communication as well! This weekend couldn’t have gone any better. If you are thinking of booking here, I absolutely recommend it! "
The price is SAR 559
SAR 1,233 total
includes taxes & fees
17 Nov - 18 Nov
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, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Beachfront paradise, relaxed, pet friendly
Livingroom
Beachfront paradise, relaxed, pet friendly
9.6 out of 10, Exceptional, (17)
"This house is exactly as advertised. You'd hardly notice it from the street but there's a nice house inside. I'm sure it has some history, given its location by the beach, and we guessed it had been gutted and renovated multiple times. It is by the beach, of course--we spent a lot of time sweeping up sand and shooing away bugs in the house, but that is what happens with kids at the beach. It was worth the great location and easy beach access. As my kids get bigger I'm not sure I'd return, but...
Beachfront paradise, relaxed, pet friendly
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
Exterior detail
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
10.0 out of 10, Exceptional, (80)
"My husband and son really loved their stay at Pat & Ken's VRBO house! They enjoyed going on walks around the neighborhood, visiting the local restaurants, and sitting in the hot tub. It was perfect for our family. Pat & Ken are such gracious hosts, and we will definitely stay here again!"
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
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.
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
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, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Pink Flamingo at the Beach
Beach
Pink Flamingo at the Beach
9.0 out of 10, Wonderful, (12)
"Great stay! Highly recommended!"
Pink Flamingo at the Beach
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
Coastal Modern Cabin - Steps to Beach!
75 inch TV with Roku, Disney +, Hulu, Netflix, Prime Video, ESPN, and more free
Coastal Modern Cabin - Steps to Beach!
9.4 out of 10, Exceptional, (10)
"3 bedrooms with plenty of room to spare! Very clean and with all the essentials. Beach access everywhere and very close to Virginia Beach."
Coastal Modern Cabin - Steps to Beach!
Sandy Mutts at the Beach
Exterior
Sandy Mutts at the Beach
8.0 out of 10, Very Good, (10)
"Sandy Mutts was a very nice place to stay, was clean and welcoming, and in a very good location. Our host was very communicative and welcoming! Will gladly come back!"
Sandy Mutts at the 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."
The price is SAR 222
SAR 737 total
includes taxes & fees
18 Nov - 19 Nov
Cozy Suite at the Beach
Shackeau East - Magnificent Views!
Popular 'Shackeau East' is not part of the Seaside Vacations' Family!
Shackeau East - Magnificent Views!
10.0 out of 10, Exceptional, (6)
"Perfect place for a weekend getaway. A peaceful little efficiency close to town but far enough off the beaten path for a great escape!"
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, (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
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
SeaLaVie!!!
Exterior
SeaLaVie!!!
9.8 out of 10, Exceptional, (37)
"On the island to visit family and wanted my own space! The cottage was perfect! The decor in line with the cottage theme! So clue and comfortable. It was the perfect setting. Quiet neighborhood. Even saw deer one morning!"
SeaLaVie!!!
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
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
Sign in
Sign up, it's free

Other property types in Chesapeake Bay

Glover Park - Georgetown
Terrace/patio
Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (2247)
"We liked room size and design, comfortable beds, cleanliness, area around. We didn't like that during check in front desk person didn't mention Wi-Fi password. "
The price is SAR 560
SAR 649 total
includes taxes & fees
24 Nov - 25 Nov
Glover Park - Georgetown
The Dupont Circle Hotel
Lobby lounge
The Dupont Circle Hotel
4.5 star property
9.4 out of 10, Exceptional, (1442)
"Comfortable hotel, and a great location. Very personal friendly service."
The price is SAR 972
SAR 1,127 total
includes taxes & fees
26 Nov - 27 Nov
The Dupont Circle Hotel
Global Luxury Suites at Capitol Hill
Exterior
Global Luxury Suites at Capitol Hill
4.0 star property
8.0 out of 10, Very Good, (407)
"Internet service including tv services out for half the trip, limited response and no communication from any hotel staff"
The price is SAR 397
SAR 896 total
includes taxes & fees
21 Nov - 22 Nov
Global Luxury Suites at Capitol Hill
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 222 and SAR 559 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 39 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.