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

Search Annapolis Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (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 ￥85,466
￥137,125 total
includes taxes & fees
Sep 27 - Sep 28
Secluded Cozy Cottage in Historic Downtown
A covered patio with a wicker sofa, a glass coffee table, a wooden table, and a bench.

2. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is ￥35,560
￥77,068 total
includes taxes & fees
Oct 8 - Oct 9
Idyllic Pasadena Retreat With Garden + Hot Tub!
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 ￥56,977
￥105,189 total
includes taxes & fees
Sep 28 - Sep 29
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 ￥40,834
￥48,757 total
includes taxes & fees
Oct 1 - Oct 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I liked the staff!"
Elliott 1-night trip
Posted 7 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Annapolis

Annapolis Cottages information

Number of reviews
22
Accommodation
15 Cottages
Lowest Price
￥48,757
Highest Price
￥137,125

Frequently asked questions

How much do cottages in Annapolis cost?
Cottages in Annapolis range between ￥48,757 and ￥137,125 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.
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.