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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chestertown cottages

A two-story house with a wooden deck, a garage, and a shed in the backyard.

1. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is Rp4.920.208
Rp5.861.198 total
includes taxes & fees
9 Nov - 10 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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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top reviews in Chestertown

A multi-story brick building with a covered entrance and a parking lot.
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown

10/10 Excellent

Rose, Carla and the other staff were fantastic. We felt so at home. Couldn't have been better. Our room was large and comfortable. We would certainly stay there again.
United Kingdom
Hugh and Lynn
Reviewed September 14, 2012
Red Roof Inn & Suites Chestertown

Frequently Asked Questions

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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.