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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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.
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.
The price is €434
includes taxes & fees
5 Nov - 6 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A building with a black metal gate, a brick pathway, and greenery.

3. 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 €611
includes taxes & fees
8 Nov - 9 Nov
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
The price is €289
includes taxes & fees
8 Nov - 9 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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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

8/10 Good
"A little noisy with doors slamming and people talking loud."
Fahim 1-night trip
Posted 23 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
118
Accommodation
61 Cottages
Lowest Price
€289
Highest Price
€611

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that travelling 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 favourite people.
How can I find cheap cottages in Chestertown?
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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.