Search Cottages in Northern Chesapeake Bay

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Compare 13 Cottages in Northern Chesapeake Bay with updated reviews, rates, and availability.

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (111)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
10.0 out of 10, Exceptional, (79)
"Firefly Cottage is a wonderful cottage! It’s clean, beautifully decorated, has high quality linens & finishes & fabulous outdoor living spaces. Pat & Ken’s hospitality & thoughtfulness helped to make our stay just perfect. "
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (132)
"Fine stay pretty quiet off season"
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, (72)
"The place is very comfortable and tucked away on the creek with nice water views. The host was accessible but I didn’t need a thing! The screened porch is a wonderful spot to enjoy my scone and tea fresh from the Great Harvest bakery just up the road. The golden sunset was a bonus each evening. "
Amazing views, short walks to great dining!
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (154)
"Great cottage along a quiet road in a private setting. This is just what my family was looking for to escape the busy weekend in Annapolis. Will not hesitate to schedule future stays at this home."
The Yellow Cottage on Harness Creek
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (20)
"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
6 Mi to Dtwn Baltimore: Home w/ Fire Pit!
3.0 star property
6 Mi to Dtwn Baltimore: Home w/ Fire Pit!
Private cottage
Private cottage
Laurel Family Home With Updates & Easy Location!
3.0 star property
Laurel Family Home With Updates & Easy Location!
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, (2233)
"Perfect location to visit our daughter. "
The price is SAR 531
SAR 616 total
includes taxes & fees
24 Nov 2024 - 25 Nov 2024
Glover Park - Georgetown
The Dupont Circle Hotel
4.5 star property
9.4 out of 10, Exceptional, (1432)
"Great location with lots of options for pubs/restaurants with Georgetown not far. Hotel is generally well maintained with friendly and knowledgeable staff. Bed is comfortable and executive room more spacious. Gym is ok. Looking overall at price and value, would likely stay elsewhere next time."
The price is SAR 935
SAR 1,084 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
The Dupont Circle Hotel
Global Luxury Suites at Capitol Hill
4.0 star property
8.0 out of 10, Very Good, (401)
"This property was unusual but delightful! I was apprehensive to book it because of reviews about access. But the Latch app was wonderful! I will definitely stay there again. "
The price is SAR 400
SAR 900 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
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 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 13 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.