Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Chestertown

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is ₩257,784
₩758,177 total
includes taxes & fees
Dec 1 - Dec 2
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Apartment (3 Bedrooms) | Interior
Trendy Baltimore Townhome: 2 Mi to Downtown!

Apartment in Patterson Park

3.5 star property
Trendy Baltimore Townhome: 2 Mi to Downtown!
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Yes, no issues"
Oronzo Reno 1-night trip
Posted 1 day ago
Comfort Inn & Suites Chestertown

Find out more about Chestertown

Search for Vacation rentals in Chestertown on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chestertown using one of the methods below:

  • View our selection of featured Vacation rentals in Chestertown
  • Use the map to find apartments and other Vacation homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Crumpton Auction, or you can go with a more secluded option if you're looking for extra privacy while you relax. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

How many vacation rentals are there in Chestertown?

Expedia has 23 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.