Photo by Julie Miller
Chestertown Vacation Rentals
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 Vacation Homes

Family Friendly - Pet Friendly
Family Friendly - Pet Friendly
9.6 out of 10, Exceptional, (55)

Family Friendly - Pet Friendly
Family Friendly - Pet Friendly
9.8 out of 10, Exceptional, (62)

Lake George Retreat
Lake George Retreat
9.6 out of 10, Exceptional, (25)

Charming cabin with three river-view decks & private setting
Charming cabin with three river-view decks & private setting
9.0 out of 10, Wonderful, (12)

Vacation Cabin minutes from Lake George w/ Hot Tub
Vacation Cabin minutes from Lake George w/ Hot Tub
10.0 out of 10, Exceptional, (8)
The price is CA $365
CA $758 total
includes taxes & fees
Aug 3 - Aug 4

Bear Cub Barn, Bolton Landing
Bear Cub Barn, Bolton Landing
10.0 out of 10, Exceptional, (1)

Terrace on the Lake – Private Lakefront with Breathtaking Views
Terrace on the Lake – Private Lakefront with Breathtaking Views
10.0 out of 10, Exceptional, (314)

Colorful adventure pad with game room & mountain/lake views - central AC
Colorful adventure pad with game room & mountain/lake views - central AC
9.8 out of 10, Exceptional, (6)
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

Baymont by Wyndham Queensbury / Lake George
10/10 Excellent
Find out more about Chestertown
Find out more about Chestertown
Chestertown Vacation Homes information
Number of reviews | 808 |
---|---|
Accommodation | 651 Vacation Homes |
Lowest Price | CA $195 |
Highest Price | CA $826 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
More Accommodation Types in Chestertown
- Cabin Rentals in Chestertown
- Cottages in Chestertown
- Apartments in Chestertown
- Motels in Chestertown
- Chalets in Chestertown
- Lodges in Chestertown
- Condo Rentals in Chestertown
- Farmstay in Chestertown
- Resorts in Chestertown
- RV Parks in Chestertown
- Castles in Chestertown
- B&B in Chestertown
- Aparthotels in Chestertown
- Guest Houses in Chestertown
- Holiday Park Resorts in Chestertown
- Inns in Chestertown
- Villas in Chestertown
- Hotels
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels
- Hotels in Niagara Falls
- Hotels in Utica
- Hotels in Lake George
- Hotels in Watertown
- Hotels in Orchard Park
- Hotels in Binghamton
- Hotels in Alexandria Bay
- Hotels with Free Airport Shuttle in Syracuse
- Hotels in Syracuse
- Hotels in Saratoga Springs
- Hotels in Lake Placid
- Hotels in Plattsburgh
- Hotels in Albany
- Hotels in Ellicottville
- Hotels in Lewiston
- Hotels in Watkins Glen
- Hotels in Ithaca
- Beach Hotel in Plattsburgh
- Hotels in Corning
Activities
Packages