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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Annapolis cottages

Exterior

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, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$433 nightly
The price is $487
Oct 5 - Oct 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Marina

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.
$760 nightly
The price is $866
Sep 20 - Sep 21
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Interior

3. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$426 nightly
The price is $485
Oct 8 - Oct 9
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor dining

4. 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.
$552 nightly
The price is $629
Sep 21 - Sep 22
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House (3 Bedrooms) | Interior

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
$270 nightly
The price is $308
Sep 21 - Sep 22
Total with taxes and fees
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Hotel is a little dated but still very well kept and a great value."
Richard 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Annapolis

Annapolis Cottages information

Number of reviews
115
Accommodation
15 Cottages
Lowest Price
$308
Highest Price
$866

Frequently asked questions

How much do cottages in Annapolis cost?
Cottages in Annapolis range between $308 and $866 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.

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