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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Northern Chesapeake Bay

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

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

10.0 out of 10, Exceptional, (91)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

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

9.8 out of 10, Exceptional, (183)
"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
Lovely backyard cottage with easy access to metro, shops, dining!
Enjoy cooking in this well-lit kitchen with a sleek island and stainless steel appliances.

Lovely backyard cottage with easy access to metro, shops, dining!

10.0 out of 10, Exceptional, (67)
"It was beautiful clean and very nice people"
Lovely backyard cottage with easy access to metro, shops, dining!
Perfect location for USNA Commissioning Week
Relax in this open-plan living area featuring a central island, dining space, and comfortable seating.

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (83)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Enjoy cooking in this well-equipped kitchen with a dishwasher and convenient access to the outdoors.

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

10.0 out of 10, Exceptional, (20)
"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 NZ$590
includes taxes & fees
17 Aug - 18 Aug
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
The Yellow Cottage on Harness Creek
Traditional house with a front porch surrounded by lush gardens and flowering plants.

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (160)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Enjoy serene sunsets over a peaceful lake or sea from a tranquil beach with a tree and rocks.

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Cozy 3BR Cottage w/Metro Access minutes to Old Town, Alexandria!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and gas stove.

Cozy 3BR Cottage w/Metro Access minutes to Old Town, Alexandria!

9.8 out of 10, Exceptional, (7)
"We had a great week in DC and this house worked out perfectly. If I needed anything Courtney was quick to respond on VRBO message page. Would definitely consider this house again if we were to return.Thank you Courtney!"
Cozy 3BR Cottage w/Metro Access minutes to Old Town, Alexandria!
1 Mi to Old Town: Historic Area Gem in Alexandria
Enjoy dining in style with a beautifully set table and comfortable seating.

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
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Stroll along the waterfront path to a historic bench, flanked by cannons, with serene views of the calm water and boats docked at the pier.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (121)
"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
Secluded Cozy Cottage in Historic Downtown
Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (12)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is NZ$1,349
includes taxes & fees
21 July - 22 July
Secluded Cozy Cottage in Historic Downtown
Game Room + Gym: Downtown DC Home!
Relax on the outdoor deck with a long sofa, armchair, and coffee table, and enjoy the convenience of a barbecue grill.

Game Room + Gym: Downtown DC Home!

3.0 star property
Game Room + Gym: Downtown DC Home!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Enjoy waterfront views from the dock, surrounded by lush greenery and serene water.

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (118)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
Situated in a serene garden, this charming shed offers a simple, functional space.

Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches

8.8 out of 10, Excellent, (5)
"The location was perfect; you can walk to the beach, stores, restaurants! Chesapeake Beach looks like a scene from Gilmore Girls! 15 minutes from a larger town with more options. 40 minute scenic drive to Annapolis or D. C. The house is small but perfect for 2 people! Be aware that the master bed is a standard size, but the second bedroom has a daybed and pull out bed! The back yard has some insecure spots if you bring a pet, but we used sections of our pet pen to cover those. And no dishwasher,...
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Enjoy a homey atmosphere on the front porch, surrounded by a small garden and a white picket fence.

6 Mi to Inner Harbor - Family Home w/ Fenced Yard!

3.0 star property
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Enjoy serene lakeside views and moored boats, perfect for a relaxing day on the water.

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

9.6 out of 10, Exceptional, (140)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Relax under a thatched umbrella in a serene outdoor setting surrounded by lush greenery.

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!
Silver Springs Home: Walk to Downtown!
House (4 Bedrooms) | Interior

Silver Springs Home: Walk to Downtown!

3.0 star property
Silver Springs Home: Walk to Downtown!
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
Adorable Family Cottage near Metro Access to DC Sleeps 8
Enjoy cooking in this well-lit kitchen with a large island, appliances, and ample cabinetry.

Adorable Family Cottage near Metro Access to DC Sleeps 8

10.0 out of 10, Exceptional, (5)
"We really enjoyed our weekend. The property is convenient to the sights of DC and the restaurants and shops in Alexandria. The host was very nice and helped us out when we had trouble with the lock."
Adorable Family Cottage near Metro Access to DC Sleeps 8
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Stayed at the Historic Inns of Annapolis - Governor Calvert House. The front desk receptionist was friendly and helpful. Check in was easy and efficient. Valet parked the car and due to being centrally located, we didn't use the car for the two days we were in Annapolis. The room was clean and the bed was comfortable. Very quiet. We would definitely stay here again! "
Mary 2-night trip
Posted 1 day ago
Historic Inns of Annapolis

Frequently asked questions

How much do cottages in Northern Chesapeake Bay cost?
Prepare to pay between NZ$590 and NZ$1,349 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 28 cottages in Northern Chesapeake Bay and then reserve your favourite. Whether you're dreaming of a holiday with the whole fam or a weekend with buddies, your ideal stay is just a few clicks away with Expedia.
What is there to do in Northern Chesapeake Bay near my cottage?
One of the best travel accessories for your Northern Chesapeake Bay holiday 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.