Photo by Julie Miller

Search Vacation Homes in Chestertown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Vacation Homes in Chestertown

Family Friendly - Pet Friendly
Outdoor dining

Family Friendly - Pet Friendly

9.6 out of 10, Exceptional, (55)
"Had a great time and was perfect for our family! "
Family Friendly - Pet Friendly
Family Friendly - Pet Friendly
Outdoor dining

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (62)
"Had a great stay, check in was easy, the house was very clean and a great location to the downtown area and easy nice walking area! Would definitely stay here again!!"
Family Friendly - Pet Friendly
Lake George Retreat
Outdoor dining

Lake George Retreat

9.6 out of 10, Exceptional, (25)
"This is a great place to stay! Very private and a perfect location. Short drive to downtown and close by restaurants and stores. The place was clean and the host was great to work with. I would definitely recommend!"
Lake George Retreat
Charming cabin with three river-view decks & private setting
Fridge, microwave, oven, stovetop

Charming cabin with three river-view decks & private setting

9.0 out of 10, Wonderful, (12)
"My family enjoyed the peaceful river noise and the fact that it was just minutes away from where we were whitewater rafting the next day!"
Charming cabin with three river-view decks & private setting
Vacation Cabin minutes from Lake George w/ Hot Tub
Fridge, microwave, oven, stovetop

Vacation Cabin minutes from Lake George w/ Hot Tub

10.0 out of 10, Exceptional, (8)
"The house is very clean and organized. "
The price is AED 973
AED 2,018 total
includes taxes & fees
4 Aug - 5 Aug
Vacation Cabin minutes from Lake George w/ Hot Tub
Bear Cub Barn, Bolton Landing
Microwave, oven, dishwasher

Bear Cub Barn, Bolton Landing

10.0 out of 10, Exceptional, (1)
"Exactly as we expected"
Bear Cub Barn, Bolton Landing
Terrace on the Lake – Private Lakefront with Breathtaking Views
Exterior

Terrace on the Lake – Private Lakefront with Breathtaking Views

10.0 out of 10, Exceptional, (314)
"Everything was excellent and the house is amazing!"
Terrace on the Lake – Private Lakefront with Breathtaking Views
Colorful adventure pad with game room & mountain/lake views - central AC
Fridge, microwave, oven, stovetop

Colorful adventure pad with game room & mountain/lake views - central AC

9.8 out of 10, Exceptional, (6)
"Our family of six loved our stay here. This rental is very clean, modern, well decorated and furnished. We loved the location, near Lake George Village and Million Dollar Beach. Stay here and you will love it too!"
Colorful adventure pad with game room & mountain/lake views - central AC
Lakeside House in Adirondacks near Lake George
Property grounds

Lakeside House in Adirondacks near Lake George

9.0 out of 10, Wonderful, (28)
"2nd year staying at this property and will be our choice for the foreseeable future"
Lakeside House in Adirondacks near Lake George
Immaculate Rental Houses in Lake George. Full Hotel Amenities. Heated Pool
Outdoor dining

Immaculate Rental Houses in Lake George. Full Hotel Amenities. Heated Pool

10.0 out of 10, Exceptional, (2)
"Fine"
Immaculate Rental Houses in Lake George. Full Hotel Amenities. Heated Pool
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
Smart TV, fireplace, books

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

10.0 out of 10, Exceptional, (21)
"We stayed here 2 yrs ago and loved it so we chose it again. A lovely and beautifully restored Victorian. Easy access to Gore. "
The price is AED 1,194
AED 1,957 total
includes taxes & fees
11 Aug - 12 Aug
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
PET-FRIENDLY - Wonderfully Situated. A Truly Beautiful Setting.
Property grounds

PET-FRIENDLY - Wonderfully Situated. A Truly Beautiful Setting.

9.2 out of 10, Wonderful, (28)
"Property was ideal for location and size for Belleayre Mtn Snowmakers during their time that they assisted Gore Mtn in making snow. Highly recommend this property."
PET-FRIENDLY - Wonderfully Situated. A Truly Beautiful Setting.
Adirondack Home on Lake Snow
Terrace/patio

Adirondack Home on Lake Snow

"The property was immaculate and the location was idyllic. It is just so peaceful and serene. Don is extremely friendly and attentive. It is perfect for campfire, swimming and kayaking. The washer and dryer as well as the WiFi and other amenities make this home an overrall perfect place!!!!"
Adirondack Home on Lake Snow
Tall pine house
3 bedrooms, WiFi, bed sheets

Tall pine house

7.6 out of 10, Good, (38)
"Parking was cramped. Great access to all village activities. Great venue area for large family groups. "
Tall pine house
SKI GORE-Central Adirondacks-60 Acre Hidden Gem, Near Schroon Lk, 15 min off I87
Outdoor dining

SKI GORE-Central Adirondacks-60 Acre Hidden Gem, Near Schroon Lk, 15 min off I87

10.0 out of 10, Exceptional, (17)
"House fully stocked with everything you need. Close to Gore mountain. Perfect spot in mountains with great views. "
SKI GORE-Central Adirondacks-60 Acre Hidden Gem, Near Schroon Lk, 15 min off I87
Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom
Property grounds

Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom

9.8 out of 10, Exceptional, (41)
"Very nice property "
Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom
Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool
Exterior

Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool

4.0 out of 10, (4)
"Property needs updating especially deck, stairway & musty odor smell."
The price is AED 2,200
AED 2,931 total
includes taxes & fees
4 Aug - 5 Aug
Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Exterior

Hickory Hill Mountaintop charming family friendly quiet very private lake view

10.0 out of 10, Exceptional, (135)
"Beautiful and spacious, clean and very accommodating. Twin beds were a bit narrow and a little uncomfortable, but definitely a great place to stay!!"
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Adirondack Bungalow Getaway
Exterior

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (57)
"Had a wonderful stay at this property. Owner was friendly and readily available. Easy to get to and good proximity to ski area. "
The price is AED 400
AED 685 total
includes taxes & fees
3 Sep - 4 Sep
Adirondack Bungalow Getaway
Secluded Gore Mountain Pine-Panelled Getaway
Exterior

Secluded Gore Mountain Pine-Panelled Getaway

9.6 out of 10, Exceptional, (136)
"Great place for a family vaca in the ADKs! Close to Gore & hiking trails, with games and places to relax in the chalet after a fun day."
Secluded Gore Mountain Pine-Panelled Getaway
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
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George

10/10 Excellent
"We had an amazing time here. Clean and comfortable. Close to the beach. "
Queenelene 2-night trip
Posted 4 hours ago
Comfort Inn & Suites Lake George