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Check prices for these dates

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Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Annapolis cottages

A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

1. 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 ￥71,316
￥112,736 total
includes taxes & fees
Nov 10 - Nov 11
Secluded Cozy Cottage in Historic Downtown
A wooden deck with wicker furniture, a round table, and a fire pit.

2. 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 ￥57,053
￥100,090 total
includes taxes & fees
Nov 10 - Nov 11
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A two-story house with a wooden deck, a garage, and a shed in the backyard.

3. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is ￥43,107
￥51,351 total
includes taxes & fees
Nov 10 - Nov 11
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 two-story white building with a central entrance, steps, and a pink door.
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
Annapolis

10/10 Excellent

Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
United States
Reyna
Reviewed February 15, 2025
134 Prince - Luxury Boutique Hotel

Frequently Asked Questions

How much do cottages in Annapolis cost?

Cottages in Annapolis range between ￥35,500 and ￥71,316 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 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.

What is there to do in Annapolis near my cottage?

Annapolis has enough sights and activities to keep you busy for weeks (or months!), beginning with William Paca House. Maryland State House, Sandy Point State Park and U.S. Naval Academy Golf Club are other impressive attractions. If you're sticking around a while, Navy-Marine Corps Memorial Stadium and U.S. Naval Academy will put the finishing touches on your itinerary.