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Search Holiday Rentals in Chestertown

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Check prices for these dates

Tonight
10 Jan - 11 Jan
Tomorrow
11 Jan - 12 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Our top choices for Chestertown holiday rentals

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

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2 reviews)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
The price is ₹14,336
₹44,902 total
includes taxes & fees
11 Jan - 12 Jan
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"H"
William 2-night trip
Posted 3 days ago
Historic Inns of Annapolis

Find out more about Chestertown

Holiday Rentals in Chestertown

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

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

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals are there in Chestertown?

Expedia has 24 holiday 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 holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.