A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Annapolis cottages

2 bedrooms, desk, iron/ironing board, free WiFi

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is AED 1,653
AED 2,730 total
includes taxes & fees
28 Jun - 29 Jun
Secluded Cozy Cottage in Historic Downtown
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
29 Jun - 30 Jun
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House (3 Bedrooms) | Front of property

Family Fun Awaits! Waterfront Home on Marley Creek

Family Fun Awaits! Waterfront Home on Marley Creek
3.0 star property
Marley
The price is AED 1,168
AED 1,511 total
includes taxes & fees
5 Jul - 6 Jul
Family Fun Awaits! Waterfront Home on Marley Creek
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is AED 2,916
AED 4,991 total
includes taxes & fees
1 Jul - 2 Jul
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
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 Annapolis Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"We were given a key to our room located at a site 2-3 blocks away. The room was lovely but the airconditioning was quite loud. We had no information given to us about facilities as the site was largely unstaffed other than cleaning and maintenance The location of the room itself was terrific."
Karen Anne 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Frequently asked questions

How much do cottages in Annapolis cost?
Cottages in Annapolis range between AED 2,441 and AED 4,991 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 14 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.
How can I find cheap cottages in Annapolis?
Expedia is here to help you track down cheap cottages in Annapolis. To find the perfect stay in a few quick clicks, try out the filter tool to refine your search by amenities, budget and star rating.