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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Cottages in Northern Chesapeake Bay

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, (76)
"Wonderful stay, truly a gem. "
Lovely backyard cottage with easy access to metro, shops, dining!
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, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (37)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK
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, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Exterior

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

10.0 out of 10, Exceptional, (22)
"We were very pleased with the location including its proximity to the sites and the neighborhood. Fran was very kind and responsive during our stay. "
The price is AED 624
AED 1,259 total
includes taxes & fees
27 Oct - 28 Oct
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior

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

9.6 out of 10, Exceptional, (143)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
The price is AED 1,653
AED 2,751 total
includes taxes & fees
5 Oct - 6 Oct
Secluded Cozy Cottage in Historic Downtown
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (168)
"A lovely property in the perfect location! We will definitely rent again!"
The Yellow Cottage on Harness Creek
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!
Exterior

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

10.0 out of 10, Exceptional, (97)
"Thanks for a great stay. The backyard was perfect for the whole family, and the house is lovely - clean, comfortable, and very well stocked! "
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!
1 Mi to Old Town: Historic Area Gem in Alexandria
House (2 Bedrooms) | Interior

1 Mi to Old Town: Historic Area Gem in Alexandria

3.0 star property
2.0 out of 10, (1)
"Everywhere dirtincluding the bath rooms. All full off old stuff."
1 Mi to Old Town: Historic Area Gem in Alexandria
4 Mi to Nationals Park: Quiet Getaway w/ Fire Pit
House (3 Bedrooms) | Interior

4 Mi to Nationals Park: Quiet Getaway w/ Fire Pit

3.0 star property
4 Mi to Nationals Park: Quiet Getaway w/ Fire Pit
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
House (3 Bedrooms) | Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is AED 691
AED 1,741 total
includes taxes & fees
5 Oct - 6 Oct
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Cottage (2 Bedrooms) | Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very Good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Game Room + Gym: Downtown DC Home!
House (5 Bedrooms) | Interior

Game Room + Gym: Downtown DC Home!

3.0 star property
Game Room + Gym: Downtown DC Home!
Ideally Located DC Home w/ Pool Table & Patio
House (3 Bedrooms) | Interior

Ideally Located DC Home w/ Pool Table & Patio

3.0 star property
2.0 out of 10, (1)
"This interestingly titled listing is certainly an affordable home option (surprised to see it on Hotels.com - property is maintained by Evolve and it is nowhere mentioned in the listing), conveniently located in the city. However, it is not recommended and not suitable for business trips. I stayed here with two colleagues during a recent business trip. The home itself is spacious, with a large living area, a patio, a nice pool table, and plenty of open parking. That said, we encountered two...
Ideally Located DC Home w/ Pool Table & Patio
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
House (4 Bedrooms) | Interior

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - <br>Navy v. South Florida 11/15/25 weekend still available!<br>Or the USNA Gospel Choir Concert weekend of 10/17/25
Exterior

Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - <br>Navy v. South Florida 11/15/25 weekend still available!<br>Or the USNA Gospel Choir Concert weekend of 10/17/25

10.0 out of 10, Exceptional, (86)
"Nice small property. Great for get aways and amazing service."
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - <br>Navy v. South Florida 11/15/25 weekend still available!<br>Or the USNA Gospel Choir Concert weekend of 10/17/25
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 Northern Chesapeake Bay Hotel Reviews

Motto by Hilton Washington DC City Center

Motto by Hilton Washington DC City Center

10/10 Excellent
"Perfect spot to stay, in an excellent location. I'll be back!"
Scott 2-night trip
Posted 4 hours ago
Motto by Hilton Washington DC City Center

Frequently asked questions

How much do cottages in Northern Chesapeake Bay cost?
Prepare to pay between AED 1,259 and AED 2,751 per night for cottages in Northern Chesapeake Bay. No matter your budget, an ideal stay is only a click or two away on Expedia. 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 through 32 cottages in Northern Chesapeake Bay and then reserve your favorite. Whether you're dreaming of a vacation with the whole fam or a weekend with buddies, your ideal stay is just a few clicks away with Expedia.
Why book your cottage in Northern Chesapeake Bay with Expedia?
Reserving a cottage in Northern Chesapeake Bay is as simple as clicking on your travel dates and choosing your ideal place for outdoor fun and relaxation. From chic retreats to inexpensive properties and cottages that offer perks like a pool, Expedia has something for all traveler styles. As for awesome deals? We've got your back!

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