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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Annapolis cottages

A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

1. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is AED 744
AED 1,178 total
includes taxes & fees
5 Oct - 6 Oct
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

2. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 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 1,928
AED 3,111 total
includes taxes & fees
2 Nov - 3 Nov
Secluded Cozy Cottage in Historic Downtown
A covered patio with a wicker sofa, a glass coffee table, a wooden table, and a bench.

3. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is AED 823
AED 1,783 total
includes taxes & fees
8 Oct - 9 Oct
Idyllic Pasadena Retreat With Garden + Hot Tub!
A wooden deck with wicker furniture, a round table, and a fire pit.

4. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
5 Oct - 6 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A two-story house with a wooden deck, a garage, and a shed in the backyard.

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is AED 948
AED 1,132 total
includes taxes & fees
4 Oct - 5 Oct
Lakefront Home Firepit BWI Marleycreek River
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Loved how the room was decorated and the atrium!"
Genevieve 2-night trip
Posted 10 hours ago
Graduate by Hilton Annapolis

Frequently asked questions

How much do cottages in Annapolis cost?
Cottages in Annapolis range between AED 1,132 and AED 3,111 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 15 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.