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Compare 19 Cottages in Annapolis with updated reviews, rates, and availability.

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, (76)
"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!
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior detail

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

10.0 out of 10, Exceptional, (81)
"A very nice and well-maintained cottage in the Cape St. Clair neighborhood where family members live. The owners have done a great job of provisioning the cottage both inside and outside, for recreational opportunities and enjoyment (barbecuing and relaxing). The backyard is very large and great for games provided with the property, like corn hole. There is also a hot tub. The owners have found the right balance for being responsive when you need them, while leaving you in peace otherwise....
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Regularly cleaned and maintained hot tub perfect for cool nights

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Secluded Cozy Cottage in Historic Downtown
Room

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (5)
"This little cottage was in an extremely convenient location. All needs within walking distance. Parking wasn’t bad - quick walk from garage. Overall would consider again!! "
The price is AED 1,377
AED 2,370 total
includes taxes & fees
7 Jan - 8 January 2025
Secluded Cozy Cottage in Historic Downtown
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Outdoor dining

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (156)
"This was a great place to relax, have time to disconnect, and time to enjoy the company of my good friend. Loved the location and walked to the winery for a fabulous afternoon picnic. "
The Yellow Cottage on Harness Creek
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Room

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

10.0 out of 10, Exceptional, (25)
"Property as described. Very clean. Appreciated having shampoo/linens. Check out easy as well. Would recommend!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Welcome to the renovated kitchen at Oh Happy Bay!

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
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Terrace/patio

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Eastport Cozy Charmer
Living area

Eastport Cozy Charmer

9.6 out of 10, Exceptional, (5)
"This property was cute, clean and the neighborhood was friendly. Close enough to walk everywhere!"
Eastport Cozy Charmer
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Terrace/patio

Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space

8.8 out of 10, Excellent, (3)
"The most lovely and completely outfitted and furnished with the latest tech and very nice amenities. The owner William answers any and all questions within minutes. The perfect spot to get away from it all yet near the Naval Academy very close by. Our first trip to this region and will not be our last."
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Walk to Everything - Historic Art’s District
Exterior

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Living area

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Terrace/patio

Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.

Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Exterior

Walk to Lake & Boat Ramp: Central Gem in Annapolis

3.0 star property
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Annapolis Home Near Beach, Dtwn & Navy Football!
Terrace/patio

Annapolis Home Near Beach, Dtwn & Navy Football!

3.0 star property
Annapolis Home Near Beach, Dtwn & Navy Football!
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 Annapolis

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

9.8 out of 10, Exceptional, (15)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views
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 Annapolis cost?
Prices for cottages in Annapolis range between AED 1,377 and AED 1,377 per night. Whatever your budget, you’ll find the perfect place to reconnect with nature. 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 Annapolis?
Take advantage of your vacation days and choose from 19 cottages in Annapolis. Picturing a place where you can get in touch with nature? Expedia can help you find the ideal stay in a few simple clicks.
Why book your cottage in Annapolis with Expedia?
We think that traveling should be stress-free, so if you’re after cottages in Annapolis at a great price, Expedia has got your back. Keep costs down and opt for a thrifty option far from the downtown buzz, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Annapolis?
Expedia is here to help you easily locate cheap cottages in Annapolis. To find the perfect stay in a few quick keystrokes, simply use our handy filter tool to refine your search results by budget, amenities and star rating.