Photo by Assya A

Chestertown Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chestertown

Other types of properties in Chestertown you may be interested in

Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (680)
"It was great"
The price is S$191
includes taxes & fees
18 Jun - 19 Jun
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, (279)
"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"
The price is S$121
includes taxes & fees
20 Jun - 21 Jun
Red Roof Inn & Suites Chestertown
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1623)
"It was our first stay in Annapolis. We were very impressed with the condition of the hotel. "
The price is S$242
includes taxes & fees
30 Jun - 1 Jul
Historic Inns of Annapolis
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.

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 30 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Wilmer Park is one spot to enjoy nature. Rolphs Wharf Marina and Crumpton Auction 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.

Recent reviews of Chestertown properties
Expedia verified reviews