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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Cottages in Chesapeake Bay

Our top choices for Chesapeake Bay cottages

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (437)
"Great place to stay!"
Key West Cottages
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Lovely backyard cottage with easy access to metro, shops, dining!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (71)
"What a perfect place to stay in a beautiful neighborhood!"
Lovely backyard cottage with easy access to metro, shops, dining!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

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

9.6 out of 10, Exceptional, (123)
"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
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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

9.8 out of 10, Exceptional, (184)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (142)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (164)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
The Hideaway Cottage
Beach nearby

The Hideaway Cottage

9.8 out of 10, Exceptional, (92)
"Just right for what we needed."
The Hideaway Cottage
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

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

9.6 out of 10, Exceptional, (119)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Exterior

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

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, Thanksgiving!
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, (123)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
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, (48)
"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
Cozy Suite at the Beach
On the beach, sun-loungers

Cozy Suite at the Beach

8.4 out of 10, Very good, (61)
"It was alright "
Cozy Suite at the Beach
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
Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks
Outdoor dining

Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks

9.8 out of 10, Exceptional, (14)
"It was a great stay! We really enjoyed the cabin! The area was nice and everyone was very friendly. We would definitely stay again!"
Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is AU$1,238
includes taxes & fees
7 Sept - 8 Sept
Secluded Cozy Cottage in Historic Downtown
Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
Property grounds

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

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

8.6 out of 10, Excellent, (14)
"Had a great time, very convenient beach access. Only complaint is there wasn’t a washer and dryer like the listing stated. Would definitely rent again."
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Pool

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

9.6 out of 10, Exceptional, (13)
"Great location, very clean and amazing staff. I highly recommend staying here."
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
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

Find out more about Chesapeake Bay

Find out more about Chesapeake Bay

Chesapeake Bay Cottages information

Number of reviews
Accommodation
80 Cottages
Lowest Price
AU$1,238
Highest Price
AU$1,238

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
You'll pay between AU$1,238 and AU$1,238 per night for cottages in Chesapeake Bay. No matter your budget, an excellent stay is only clicks away on Expedia. This price was 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?
Browse through our 80 cottages in Chesapeake Bay and then choose your favourite. Whether you're embarking on a family holiday or a break with pals, your ideal stay is just clicks away with Expedia.
What is there to do in Chesapeake Bay near my cottage?
Whether you're interested in history, food, shopping or sightseeing, Chesapeake Bay is one place you'll never get bored! The awesome city of Washington has plenty of things to do and see, including National Mall, Smithsonian Institution and National Museum of African American History and Culture. If you're headed to Baltimore, National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum are must-do's.