Vacation Rentals

Chestertown Vacation Rentals

Aurora Rossi

Are you in a hurry?

Here is a quick list of Vacation Rentals in Chestertown, selected based on their rating

Name of hotel Accommodation Rating Price, $
Rustic Adirondacks Home W/ Hot Tub & Lake Access!

9.7 / 10

(3 Reviews)

 From 471$
Adirondack Oasis, 15 Mi To Lake George Village!

10.0 / 10

(2 Reviews)

 From 657$
Town House Lodge

8.4 / 10

(380 Reviews)

 From 124$
The Devlin

8.7 / 10

(491 Reviews)

 From 244$
Modern Studio < 13 Mi To Saratoga Racetrack!

10.0 / 10

(7 Reviews)

 From 129$

Vacation rentals in Chestertown offer a unique option for travelers seeking both comfort and charm. This picturesque town, located along the Sassafras River, provides visitors with an array of rental choices ranging from cozy cottages to spacious homes. Whether one prefers a waterfront view or a central location, Chestertown has something that caters to every taste. This guide will help you navigate the distinctive offerings that make vacationing here a memorable experience.

Best Chestertown Vacation Rentals

Table of contents

Rustic Adirondacks Home W/ Hot Tub & Lake Access! Adirondack Oasis, 15 Mi To Lake George Village! Eagles Nest At Loon Lake Near Gore Mountain 4 Mi To Beach & Lake: Spacious Home In Chestertown Lily Pad North At Loon Lake Near Gore Mountain The Lily Pad At Loon Lake Near Gore Mountain Cozy Adirondack Jem Your Four Season Getaway Year-Round Loon Lake Retreat: Ski, Hike, Explore! Lakefront Townhome Chestertown "Lakeside Escape" Private Dock & Beach! Lakefront, Fire Pit, Boats

View all photos

9.7
Excellent
3 Reviews

Rustic Adirondacks Home W/ Hot Tub & Lake Access!

📍 7133 U.S. 9

From 471$

Check Availability

View all photos

10
Excellent
2 Reviews

Adirondack Oasis, 15 Mi To Lake George Village!

📍 105 Balsam Crest Rd

From 657$

Check Availability

View all photos

10
Excellent
2 Reviews

Eagles Nest At Loon Lake Near Gore Mountain

📍 7129 U.S. 9
Check Availability

View all photos

10
Excellent
2 Reviews

4 Mi To Beach & Lake: Spacious Home In Chestertown

📍 189 Stock Farm Rd
Check Availability

View all photos

9.5
Excellent
2 Reviews

Lily Pad North At Loon Lake Near Gore Mountain

📍 North 7131 U.S. 9
Check Availability

View all photos

The Lily Pad At Loon Lake Near Gore Mountain

📍 North & South 7131 U.S. 9
Check Availability

View all photos

Cozy Adirondack Jem Your Four Season Getaway

📍 3 High Pines Terrace E
Check Availability

View all photos

Year-Round Loon Lake Retreat: Ski, Hike, Explore!

📍 33 Loon Lake Heights Rd
Check Availability

View all photos

Lakefront Townhome Chestertown "Lakeside Escape"

📍 16 Evergreen Way
Check Availability

View all photos

Private Dock & Beach! Lakefront, Fire Pit, Boats

📍 206 Hill Park Rd
Check Availability

View all photos

All-Season Family Retreat W/ Dock On Loon Lake!

📍 13 Marina Rd
Check Availability

View all photos

Pine Tree Cove On Friends Lake

📍 948 Friends Lake Road
Check Availability

View all photos

8.4
Very good
380 Reviews

Town House Lodge

📍 2267 Saranac Avenue

From 124$

Check Availability

View all photos

8.7
Excellent
491 Reviews

The Devlin

📍 2764 Main Street

From 244$

Check Availability

View all photos

10
Excellent
7 Reviews

Modern Studio < 13 Mi To Saratoga Racetrack!

📍 90 Lasher Rd

From 129$

Check Availability

View all photos

9.3
Excellent
9 Reviews

Seven Dwarfs Cabin - On The Brook Cabins

📍 468 Canada St

From 89$

Check Availability

View all photos

8.6
Excellent
73 Reviews

Maple Leaf Lodge

📍 1370 U.S. 9

From 129$

Check Availability

View all photos

9.9
Excellent
39 Reviews

Robert Frost Mountain Cabins

📍 2430 North Branch Road

From 352$

Check Availability

View all photos

9.5
Excellent
26 Reviews

New 3 Bedroom - Thoroughbred Farm & Lake Views!

📍 10 Brock Drive

From 302$

Check Availability

View all photos

10
Excellent
8 Reviews

Adirondack Mountains Cottage Near Gore Mountain!

📍 12 The Loop, Warrensburg, NY 12885, US

From 272$

Check Availability

Location