Photo by Assya A

Search Holiday Rentals in Chestertown

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Chestertown

Other types of properties in Chestertown you may be interested in

Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (676)
"The onsite manager was very helpful. The staff was very nice. "
The price is ₹10,362
per night
29 May - 30 May
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, (269)
"Sometimes, you don’t need a fancy place; just a clean place. That’s what this is. Maybe there weren’t the newest finishes, but we really appreciated having the extra pull-out couch and space in the room. It was perfect for traveling with my 3 teenagers."
The price is ₹7,062
per night
29 May - 30 May
Red Roof Inn & Suites Chestertown
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1620)
"Myra at checkin was great!!!"
The price is ₹13,286
per night
16 Jun - 17 Jun
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.

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 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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

5/5 Excellent
"Nice would recommend "
A verified traveller from Brooklyn stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh