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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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

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, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
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
Front of Carpenter St. Cottage

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

9.8 out of 10, Exceptional, (172)
"Host was amazing. Property is perfect. Will be staying here again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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, (77)
"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!
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
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (157)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Exterior detail

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

10.0 out of 10, Exceptional, (85)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.

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

9.6 out of 10, Exceptional, (135)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
2 Mi to National Mall: Modern DC Home
Living area

2 Mi to National Mall: Modern DC Home

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...
2 Mi to National Mall: Modern DC Home
Maryland Home w/ Deck: 8 Mi to Washington, DC
Exterior

Maryland Home w/ Deck: 8 Mi to Washington, DC

3.0 star property
Maryland Home w/ Deck: 8 Mi to Washington, DC
Elegant Fort Washington Home Near National Harbor!
Living area

Elegant Fort Washington Home Near National Harbor!

3.0 star property
Elegant Fort Washington Home Near National Harbor!
Alexandria Area Vacation Rental 15 Mi to DC!
Exterior

Alexandria Area Vacation Rental 15 Mi to DC!

3.0 star property
Alexandria Area Vacation Rental 15 Mi to DC!
Laurel Family Home With Updates & Easy Location!
Exterior

Laurel Family Home With Updates & Easy Location!

3.0 star property
Laurel Family Home With Updates & Easy Location!
Spacious Fort Washington Home Near National Mall!
Living area

Spacious Fort Washington Home Near National Mall!

3.0 star property
Spacious Fort Washington Home Near National Mall!
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

ARC HOTEL Washington DC, Georgetown
Exterior

ARC HOTEL Washington DC, Georgetown

3.0 star property
8.2 out of 10, Very Good, (2180)
"Michelle, the receptionist, was extremely helpful and went above and beyond in making my stay enjoyable. "
The price is SAR 380
SAR 440 total
includes taxes & fees
1 Feb - 2 Feb
ARC HOTEL Washington DC, Georgetown
Glover Park - Georgetown
Terrace/patio

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2301)
"I had a wonderful stay at this hotel! The boutique ambiance was charming and added a unique touch to my visit. The room was spacious, providing plenty of comfort, and the beds were incredibly cozy, ensuring a restful night’s sleep. The location was perfect, making it easy to explore the surrounding area with everything conveniently nearby. I also enjoyed dining at the hotel’s restaurant, which offered delicious food and excellent service. Overall, this hotel exceeded my expectations, and I would...
The price is SAR 603
SAR 699 total
includes taxes & fees
29 Jan - 30 Jan
Glover Park - Georgetown
The Dupont Circle Hotel
Lobby lounge

The Dupont Circle Hotel

4.5 star property
9.4 out of 10, Exceptional, (1486)
"I love the Dupont Circle Hotel, and this is the only place I stay while in DC. Their furniture on my latest stay was looking a little worse for wear, but I think a small spruce up will bring it back to its former glory. Maybe update the carpet and the furniture facings. But the amenities, restaurants, and room service are too notch. The street facing rooms can get a bit noisy. "
The price is SAR 1,009
SAR 1,170 total
includes taxes & fees
30 Jan - 31 Jan
The Dupont Circle Hotel
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 and 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?
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