Search Northern Chesapeake Bay Cottage Rentals from CA $259

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Northern Chesapeake Bay Cottages

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, (44)
"Clean and comfortable. Well stocked. We cooked a few breakfasts and found the pans and utensils to be in great shape. Appliances and climate control easy to use. Host extremely responsive. We stayed four nights with no car, easily walking to the Metro and a variety of good restaurants (we are seniors). That said, I docked one star from location because I would have preferred the Metro and restaurants to be a few blocks closer considering how much walking we did visiting tourist sites in DC. We...
The price is CA $259
CA $337 total
includes taxes & fees
Apr 9 - Apr 10
Lovely backyard cottage with easy access to metro, shops, dining!
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, (175)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
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
Miscellaneous

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

10.0 out of 10, Exceptional, (14)
"Just as advertiwed. Host was available and east to reach, responsive."
The price is CA $288
CA $557 total
includes taxes & fees
Apr 13 - Apr 14
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
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, (117)
"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
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
On the beach, sun loungers, beach towels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
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, (136)
"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Amazing views, short walks to great dining!
View from property

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (78)
"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!
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
1 Mi to Old Town: Historic Area Gem in Alexandria
Interior

1 Mi to Old Town: Historic Area Gem in Alexandria

3.0 star property
1 Mi to Old Town: Historic Area Gem in Alexandria
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, (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!
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (8)
"Perfect location for family visit at USNA! House was super clean and cozy with easy access to all downtown and academy events."
The price is CA $644
CA $1,062 total
includes taxes & fees
Apr 6 - Apr 7
Secluded Cozy Cottage in Historic Downtown
Walk Downtown: Takoma Park Escape w/ Large Yard!
Interior

Walk Downtown: Takoma Park Escape w/ Large Yard!

3.0 star property
Walk Downtown: Takoma Park Escape w/ Large Yard!
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
Exterior

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2358)
"The room was super clean and smelled nice. The beds were comfortable. Room had a nice view of the street. Even the hallways were nice, well decorated, well lit and good smelling. Check in and check out was smooth and quick. The restaurant— Divino had good food. Great location. We enjoyed our stay and would definitely be staying here again. "
The price is CA $218
CA $252 total
includes taxes & fees
Apr 19 - Apr 20
Glover Park - Georgetown
The Churchill Hotel near Embassy Row
Exterior

The Churchill Hotel near Embassy Row

3.5 star property
8.8 out of 10, Excellent, (1679)
"it was a great stay- but the luggage guy was a little rude! "
The price is CA $180
CA $251 total
includes taxes & fees
Apr 13 - Apr 14
The Churchill Hotel near Embassy Row
The River Inn
Hypo-allergenic bedding, in-room safe, desk, laptop workspace

The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1628)
"Very clean and comfortable. Service is great! Exceeded expectations. "
The price is CA $226
CA $262 total
includes taxes & fees
Apr 19 - Apr 20
The River Inn
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?
Prepare to pay between CA $259 and CA $644 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 12 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!
How can I find cheap cottages in Northern Chesapeake Bay?
Expedia can help you easily source cheap cottages in Northern Chesapeake Bay. To find a fantastic stay in a couple of quick clicks, use our convenient filter tool to refine your search results by amenities, star rating and budget.
What is there to do in Northern Chesapeake Bay near my cottage?
One of the best travel accessories for your Northern Chesapeake Bay vacation is an awesome itinerary! Arlington House-The Robert E. Lee Memorial, Cady’s Alley and Francis Scott Key Memorial Park are some of the leading sights if you’re heading to Washington. Baltimore also has plenty of big-name attractions, such as Geppi’s Entertainment Museum. Eager to explore more? Visit Union Soldiers and Sailors Monument and Edgar Allan Poe’s Gravesite and Memorial too.