Photo by Assya A

Chestertown Vacation 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

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Chestertown

Save an average of 15% on thousands of hotels when you're signed in

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, (743)
"Friendly atmosphere and well stocked breakfast bar! Comfortable clean room! "
The price is NT$3,499
NT$3,884 total
includes taxes & fees
Feb 16 - Feb 17
Comfort Inn & Suites Chestertown

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (994)
"Our go-to hotel for the staff, amenities, and location! "
The price is NT$10,327
NT$13,478 total
includes taxes & fees
Feb 13 - Feb 14
Sagamore Pendry Baltimore

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
7.2 out of 10, Good, (1003)
"It was amazing "
The price is NT$1,809
NT$2,026 total
includes taxes & fees
Feb 2 - Feb 3
Quality Inn & Suites Bel Air I-95 Exit 77A
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 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 26 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Wilmer Park and Roundtop Park, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Rolphs Wharf Marina and Crumpton Auction 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.