An aerial view of a town with a river, buildings, and surrounding greenery.

Search Chestertown Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chestertown cottages

A wooden deck with wicker furniture, a round table, and a fire pit.

1. 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.
$583 nightly
The price is $665
Oct 28 - Oct 29
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A house with a red door, a small porch, and a view of a river with a bridge in the background.

2. 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.
$463 nightly
The price is $521
Nov 5 - Nov 6
Total with taxes and fees
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.

3. 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.
$702 nightly
The price is $800
Nov 1 - Nov 2
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
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
$284 nightly
The price is $324
Oct 28 - Oct 29
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.
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 Chestertown Hotel Reviews

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"I specifically chose this hotel because they had a hot tub and they were close to a physically demanding job that I was doing 2 days in a row. I had hoped to get some relaxation and relief but the hot tub was broken. The pool was relaxing enough but it seemed like it was ready for a good cleaning as was the area around the pool deck. There were no lights on when I arrived at the pool so I had to go to the front desk and the clerk attended to the issue quickly and walked down to the pool area and turned lights on for me. Most of the common areas were clean enough but some areas (like around the ice machines and where the vending machines used to be) were pretty grubby and nasty. One set of blinds was so broken and filthy that they should have just removed them completely for some improvement. The room was clean but a bit dated. There was shampoo, conditioner, liquid body soap and body lotion available if I had wanted them. There were also 2 small bars of soap for the sink area. The towels were clean and there were 2 sets in the room (I used both for one overnight stay as the bath towels were on the small side). The bed was comfortable enough but the plush armchair was so old and filthy I couldn't bring myself to sit on it but the desk chair did nicely. The breakfast was almost edible but I would plan on sticking to the fresh fruit and packaged yogurt. Overall it was decent enough that I would stay here again for a quick overnight between work days."
Teresa Marie 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Baltimore North, MD

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
116
Accommodation
64 Cottages
Lowest Price
$324
Highest Price
$800

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that traveling should be stress-free, so if you're chasing cottages in Chestertown at a competitive rate, Expedia delivers. Save cash and select a wallet-friendly option surrounded by nature, or book an upmarket cottage to pamper your favorite people.
How can I find cheap cottages in Chestertown?
The simplest way to track down cheap cottages in Chestertown is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.
What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.

Explore a world of travel with Expedia