Photo by Assya A
Find Cabins in Chestertown for Rent
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Chestertown Cabin Rentals
Recommended hotels in Chestertown

The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
8.2 out of 10, Very good, (61)
The price is CA $183
CA $203 total
includes taxes & fees
Aug 19 - Aug 20

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (794)
The price is CA $157
CA $175 total
includes taxes & fees
Aug 24 - Aug 25

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.2 out of 10, Good, (386)
The price is CA $99
CA $110 total
includes taxes & fees
Aug 24 - Aug 25

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (98)
The price is CA $124
CA $206 total
includes taxes & fees
Aug 20 - Aug 21

Quality Inn
Quality Inn
7.6 out of 10, Good, (1000)
The price is CA $123
CA $136 total
includes taxes & fees
Sep 17 - Sep 18

Relax Inn Smyrna
Relax Inn Smyrna
7.8 out of 10, Good, (86)
The price is CA $123
CA $137 total
includes taxes & fees
Aug 19 - Aug 20

Hampton Inn Middletown
Hampton Inn Middletown
8.8 out of 10, Excellent, (820)
The price is CA $152
CA $168 total
includes taxes & fees
Aug 24 - Aug 25

Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHG
9.2 out of 10, Wonderful, (604)
The price is CA $160
CA $178 total
includes taxes & fees
Aug 24 - Aug 25
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Chestertown Hotel Reviews

Fairfield Inn & Suites by Marriott White Marsh
10/10 Excellent
Find out more about Chestertown
Find out more about Chestertown
Chestertown Cabin Rentals information
Number of reviews | 84 |
---|---|
Accommodation | 3 Cabin Rentals |
Lowest Price | |
Highest Price |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
- Cabin Rentals in Pomona
- Cabin Rentals in Georgetown
- Cabin Rentals in Church Hill
- Cabin Rentals in Great Oak Landing
- Cabin Rentals in Tolchester Beach
- Cabin Rentals in Crumpton
- Cabin Rentals in Rock Hall
- Cabin Rentals in Sudlersville
- Cabin Rentals in Centreville
- Cabin Rentals in Worton
- Cabin Rentals in Kennedyville
- Cabin Rentals in Millington
Top Cabin Rentals in Other Destinations
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown
- Apartments in Chestertown
- Cottages in Chestertown
- Guest Houses in Chestertown
- Motels in Chestertown
- Houseboats in Chestertown
- RV Parks in Chestertown
- B&B in Chestertown
- Farmstay in Chestertown
- Condo Rentals in Chestertown
- Villas in Chestertown
- Lodges in Chestertown
- Hotels
All Accommodation Types
Be inspired: Top Cabin Rentals destinations in 2025
- Jasper National Park Cabins
- Tofino Cabins
- Algonquin Park Cabins
- Cultus Lake Cabins
- Waterton Park Cabins
- Squamish Cabins
- Sunshine Coast Cabins
- Hope Cabins
- Radium Hot Springs Cabins
- Kananaskis Cabins
- Jasper Cabins
- Revelstoke Cabins
- Harrison Hot Springs Cabins
- Calgary Cabins
- Canmore Cabins
- Chilliwack Cabins
- Northern Ontario Cabins
- Fernie Cabins
- Kenora Cabins
- Drumheller Cabins
More ways to book
Expedia's Latest Trends
Hotels
- Best Hotels in Niagara Falls
- Best Hotels in Honolulu
- Best Hotels in Bangor
- Best Hotels in Grand Forks
- Best Hotels in Kalispell
- Best Hotels in Fargo
- Best Hotels in Ocean City
- Best Hotels in Frederick
- Best Hotels in Silver Spring
- Best Hotels in Palm Springs
- Ocean City Oceanfront Hotels
- Best Hotels in Annapolis
- Best Hotels in Hagerstown
Packages
Vacation Rentals