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Check prices for these dates

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15 Aug - 17 Aug
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5 Sept - 7 Sept
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3 Oct - 5 Oct

Featured Cottages in Chesapeake Bay and around

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (419)
"Beautiful pool areas, lots to do, and plenty of room with a family of 5! "
Key West Cottages
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

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

9.6 out of 10, Exceptional, (121)
"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
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Beach

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (46)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Beach nearby

Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

8.0 out of 10, Very good, (4)
"The location is great for a family with pets. The check in and out process was simple and the host was responsive. No complaints! "
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Lovely backyard cottage with easy access to metro, shops, dining!
Exterior

Lovely backyard cottage with easy access to metro, shops, dining!

10.0 out of 10, Exceptional, (68)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!
Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg
Exterior

Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg

8.0 out of 10, Very good, (1)
"This listing says cottage but it's an apartment. Be ready to go up stairs to get into it. The kitchen is small but fine. Everything works, but it's not especially well equipped for cooking. The coffee maker does not work. Our checkin was delayed for about 40 minutes when we arrived and we had no where to stay while waiting for our apartment. Wi Fi was very weak in the apartment and TV is like a hotel where there are certain channels available but no way to sign in to your own streaming accounts....
Charming 2-bedroom cottage with AC, fitness room, WiFi in welcoming Williamsburg
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (162)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning
Beach nearby

Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning

8.4 out of 10, Very good, (5)
"Our stay was nice. The house was clean."
Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Exterior

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

10.0 out of 10, Exceptional, (121)
"My three sisters and I had a wonderful stay! The house was clean, updated, and in a great location. We highly recommend!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Exterior

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (51)
"Wonderful golf cart community! Perfect way to relax, short walk to the water in either direction. Meet allot of the locals, enjoyed the local breweries and restuarants."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Pink Flamingo at the Beach
Exterior

Pink Flamingo at the Beach

8.6 out of 10, Excellent, (16)
"older place but very nice and close to the beach"
Pink Flamingo at the Beach
Cozy Suite at the Beach
On the beach, sun-loungers

Cozy Suite at the Beach

8.4 out of 10, Very good, (59)
"It was alright "
Cozy Suite at the Beach
Small cottage for those little getaways
Exterior

Small cottage for those little getaways

10.0 out of 10, Exceptional, (112)
"Great place, cozy and easy to park and get around. "
Small cottage for those little getaways
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
On the beach

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

9.0 out of 10, Wonderful, (99)
"If you’re looking for a place for you to have a safe space with your family, young or old, with all the amenities that you would want from your own home this is it. If you’re a veteran, there’s multitude of bases nearby with commissary’s to get groceries for the week to help the budget. "
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor dining

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Treetop Rustic Beach Front 2 Bedroom Apartment
Exterior

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (23)
"Repeat guest.. stayed in another unit previously *loft property.Property is very close to the beach, can walk into the sand from the property. Pet friendly is a plus.. lots of doggos on the beach.Property has the basics.. minimal items in unit, so you need to bring quite a bit of things to make your trip complete. Owners have several units, so amenities are shared. Husband and I used the charcoal grill and set by the firepit in the sand. Not sure id stay in this particular unit again, but id...
Treetop Rustic Beach Front 2 Bedroom Apartment
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

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

9.8 out of 10, Exceptional, (184)
"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
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
Exterior

Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

7.0 out of 10, Good, (13)
"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
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
Exterior

Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

9.8 out of 10, Exceptional, (26)
"Vacation very enjoyable and peaceful"
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
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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Top Chesapeake Bay Hotel Reviews

Omni Shoreham Hotel

Omni Shoreham Hotel

10/10 Excellent
"amazing "
Bassem 2-night trip
Posted 14 hours ago
Omni Shoreham Hotel

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
Rates for cottages in Chesapeake Bay range between and 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 54 cottages in Chesapeake Bay. Whether you're travelling 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!