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Compare 12 Cottages in Northern Chesapeake Bay with updated reviews, rates, and availability.

Lovely backyard cottage with easy access to metro, shops, dining!
10.0 out of 10, Exceptional, (22)
"Best rental we have ever booked! Exactly as advertised. Incredibly clean and comfortable. Thanks Geneva!"
The price is ¥26,309
¥34,122 total
includes taxes & fees
Oct 5 - Oct 6
Lovely backyard cottage with easy access to metro, shops, dining!
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (76)
"The cottage was a great place to stay with charming outdoor spaces nestled in a lovely neighborhood with easy access to Sandy Point and other local attractions. The hosts were gracious and ensured our needs were met throughout our stay."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (150)
"The Yellow Cottage was a perfect spot for my daughter and I to spend the weekend near Annapolis. The location was perfect, near the city but also very close to a delightful winery. Everything was provided which means you can pack lightly. We unfortunately did not have the opportunity to hit the water on this trip. "
The Yellow Cottage on Harness Creek
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
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
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (71)
"Our stay at this Vrbo in Annapolis was nothing short of spectacular! The property is beautifully maintained, offering the perfect blend of comfort and style. The attention to detail was evident, from the cozy living spaces to the well-appointed kitchen that had everything we needed for our stay. The location is unbeatable—close enough to all the attractions, restaurants, and shops make Annapolis the charming city that it is (1.2 miles walk to the Naval Academy), while distanced enough to be a...
Amazing views, short walks to great dining!
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
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (19)
"This cottage sits in an amazing peaceful location on the water and was an oasis for 5 girlfriends to spend several days together and explore Annapolis. We thoroughly enjoyed the spaces, had plenty of room for all of us to stay. The staircase is a bit off-putting if you are trying to carry anything downstairs but it is very easy to navigate otherwise for 5 50-70 year olds without mobility issues. And you can also go outside and walk down the stairs instead if needed. The beds and seating were...
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Modern DC Vacation House - 2 Mi to National Mall!
3.0 star property
8.6 out of 10, Excellent, (4)
"My daughter's family and myself went to DC for my mother's burial at Arlington. It was a quick trip and we're from the area,though no one lives there now, so we needed a place to stay. This was a convenient location close to places to eat, the Metro, and major roadways. It was clean, comfortable, and safe. I'd definitely recommend. The only negative was the lot parking spot was a little tricky but the on street parking is a good alternative. There were a couple spots the paint needs to be...
Modern DC Vacation House - 2 Mi to National Mall!
The Carriage House at Historic Belle Grove Manor
The Carriage House at Historic Belle Grove Manor
Private cottage
Private cottage
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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 Northern Chesapeake Bay

Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (2196)
"Nice spacious hotel in Georgetown . Little dated but god value . Don’t desk receptionists are all amazing. "
The price is ¥27,407
¥31,778 total
includes taxes & fees
Oct 6 - Oct 7
Glover Park - Georgetown
Embassy Suites by Hilton Washington D.C. – Convention Center
3.5 star property
8.8 out of 10, Excellent, (2262)
"Would definitely return."
The price is ¥33,886
¥39,291 total
includes taxes & fees
Oct 6 - Oct 7
Embassy Suites by Hilton Washington D.C. – Convention Center
Hilton Garden Inn Washington DC/U.S. Capitol
3.0 star property
7.8 out of 10, Good, (2053)
"I loved the front desk clerk he was up beat and friendly. He serviced me quickly and made light convo and cracked a joke or two."
The price is ¥25,620
¥29,707 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Garden Inn Washington DC/U.S. Capitol
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 Northern Chesapeake Bay cost?
Cottages in Northern Chesapeake Bay range between ¥26,309 and ¥26,309 per night. These properties offer a chance to touch base with nature — at a price you can afford. 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 Northern Chesapeake Bay?
Browse our 12 cottages in Northern Chesapeake Bay and then book your favorite. Whether you’re embarking on a vacation with the whole fam or a weekend with besties, your perfect stay is a few clicks away with Expedia.
Why book your cottage in Northern Chesapeake Bay with Expedia?
We think that vacations should be easy, so if you’re seeking cottages in Northern Chesapeake Bay at a competitive price, Expedia can help. Save money and opt for a cheap option far away from the city rush, or splurge on an upmarket cottage to pamper your favorite people.
How can I find cheap cottages in Northern Chesapeake Bay?
With Expedia’s convenient filter tool, locating cheap cottages in Northern Chesapeake Bay is a snap. To find accommodations that’ll make your bank balance smile, refine your search by amenities, budget and star rating.
What is there to do in Northern Chesapeake Bay near my cottage?
Whatever your interests, there are lots of things to keep you busy in Northern Chesapeake Bay. If you’re headed to Washington, drop by National Mall, National Air and Space Museum and Smithsonian’s National Zoo. Spending your vacay in Baltimore? National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum are popular sights here.