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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Annapolis cottages

A house with a red door, a small porch, and a view of a river with a bridge in the background.

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.
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, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is AU$1,043
includes taxes & fees
9 Nov - 10 Nov
Secluded Cozy Cottage in Historic Downtown
A wooden deck with wicker furniture, a round table, and a fire pit.

3. 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 AU$879
includes taxes & fees
9 Nov - 10 Nov
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A two-story house with a wooden deck, a garage, and a shed in the backyard.

4. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is AU$472
includes taxes & fees
9 Nov - 10 Nov
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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Annapolis and related destinations

Cobblestone streets wind past the Naval Academy where midshipmen march in crisp white uniforms during ceremonial parades. Sail the Chesapeake Bay in the morning, then explore historic homes and seafood spots along the charming waterfront district.

See all hotels in Annapolis
A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

Top reviews in Annapolis

A brick building with a large entrance and a sign reading "Graduate Annapolis."
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis

10/10 Excellent

Great hotel. Booked room with balcony and valet parking included and well worth it, spacious. Walking distance to Main Street, fabulous happy hour at O’Briens Oyster Bar would highly recommend. Staff friendly and helpful. You won’t regret it.
Australia
Bridget
Reviewed April 8, 2023
Graduate by Hilton Annapolis

Frequently Asked Questions

How much do cottages in Annapolis cost?

You can expect to pay between AU$471 and AU$1,043 per night for cottages in Annapolis. Whatever your budget, an epic stay is a click away on Expedia. This price was 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.

What is there to do in Annapolis near my cottage?

There are tons of superb things to sink your teeth into in Annapolis. Drop by top attractions like Sandy Point State Park, Sandy Point Beach and Triton Beach. Matapeake State Park, Bay Ridge Beach and Annapolis Bowl are other must-see's.