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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 18 Cottages in Annapolis with updated reviews, rates, and availability.

Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (9)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is AED 2,204
AED 3,446 total
includes taxes & fees
6 Jun - 7 Jun
Secluded Cozy Cottage in Historic Downtown
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, (27)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets,
Exterior

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

10.0 out of 10, Exceptional, (87)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets,
Perfect location for USNA Commissioning Week
View from property

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (82)
"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."
Perfect location for USNA Commissioning Week
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

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

9.8 out of 10, Exceptional, (28)
"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
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

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

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

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
The Yellow Cottage on Harness Creek
Smart TV, DVD player, books

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (157)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
2 Mi to Sandy Point State Park: Home w/ Deck!
Interior

2 Mi to Sandy Point State Park: Home w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean and nice. The beds choices were comfortable and keyless checkin was convenient. "
2 Mi to Sandy Point State Park: Home w/ Deck!
Walk to Everything - Historic Art’s District
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Living area

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

The price is AED 2,204
AED 3,827 total
includes taxes & fees
30 May - 31 May
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Annapolis Home Near Beach & Quiet Waters Park!
Interior

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
On the beach, sun loungers, beach towels

Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly

9.8 out of 10, Exceptional, (30)
"Really like this place "
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Interior

Walk to Lake & Boat Ramp: Central Gem in Annapolis

3.0 star property
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Outdoor spa tub

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Escape to Downtown Annapolis Murray Hill with Luxe King Suite and Porch Vibes
Private kitchen

Escape to Downtown Annapolis Murray Hill with Luxe King Suite and Porch Vibes

Escape to Downtown Annapolis Murray Hill with Luxe King Suite and Porch Vibes
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Beach

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

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

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

10.0 out of 10, Exceptional, (218)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AED 3,276
AED 5,217 total
includes taxes & fees
10 Jun - 11 Jun
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Beach

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (69)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
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?
Cottages in Annapolis range between AED 2,204 and AED 2,204 per night. These properties offer a chance to get in touch 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 Annapolis?
You can choose from 18 cottages in Annapolis. No matter if you’re vacationing with the family or planning a weekend retreat with your buddies, Expedia can help you find the right place to reacquaint yourself with nature.
Why book your cottage in Annapolis with Expedia?
Expedia has some terrific cottages in Annapolis, so get ready for an unforgettable vacation on nature’s doorstep. If you have a budget, click on how much you’d like to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with free WiFi or a pool. We’ll help you find the perfect fit whatever your trip looks like.