Holiday Homes in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Our top choices for Chestertown holiday homes

Exterior

Holiday Home in Chestertown

Eagles Nest at Loon Lake near Gore Mountain
10.0 out of 10, Exceptional, (115 reviews)
"Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion. "
United States
Kathy B.
The price is NZ$1,133
includes taxes & fees
8 Mar - 9 Mar
Eagles Nest at Loon Lake near Gore Mountain
Outdoor dining

Holiday Home in Chestertown

The Lily Pad at Loon Lake near Gore Mountain
9.6 out of 10, Exceptional, (40 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is NZ$793
includes taxes & fees
4 Mar - 5 Mar
The Lily Pad at Loon Lake near Gore Mountain
Smart TV

Holiday Home in Lake Luzerene

Vacation Cabin minutes from Lake George w/ Hot Tub
10.0 out of 10, Exceptional, (13 reviews)
"This was our second time staying at Potash Road. Just like the first time, it was a wonderful experience. We will definitely be booking here again."
United States
Laurie S.
The price is NZ$779
includes taxes & fees
4 Mar - 5 Mar
Vacation Cabin minutes from Lake George w/ Hot Tub
Beach

Holiday Home in Diamond Point

True Adirondack living. 3-bedroom house in tranquil Diamond Point.
10.0 out of 10, Exceptional, (9 reviews)
"Fantastic stay. Clean and welcoming. Plenty of staples supplied which is always helpful. Will visit again."
United States
Brad S.
The price is NZ$1,133
includes taxes & fees
4 Mar - 5 Mar
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Exterior

Holiday Home in Olmstedville

NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
10.0 out of 10, Exceptional, (8 reviews)
"Exactly what we needed & was stocked with great games, cooking supplies & blankets! Can’t wait to come back."
United States
Katlyn H.
The price is NZ$1,295
includes taxes & fees
4 Mar - 5 Mar
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
Outdoor dining

Holiday Home in Warrensburg

Adirondack Bungalow Getaway
10.0 out of 10, Exceptional, (71 reviews)
"Great spot "
United States
Winter R.
The price is NZ$320
includes taxes & fees
16 Mar - 17 Mar
Adirondack Bungalow Getaway
Property grounds

Holiday Home in Minerva

Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
10.0 out of 10, Exceptional, (1 review)
"Absolutely fantastic! Hosts were very kind and responsive. Property was clean and cozy. "
United States
Christine T.
The price is NZ$428
includes taxes & fees
9 Mar - 10 Mar
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Property grounds

Holiday Home in North Creek

Lovely 3-bedroom house close to Gore Mountain for skiing.
10.0 out of 10, Exceptional, (1 review)
"Brittany was super responsive and welcoming. "
United States
dana c.
The price is NZ$740
includes taxes & fees
7 Mar - 8 Mar
Lovely 3-bedroom house close to Gore Mountain for skiing.
Interior

Holiday Home in North River

Sweet New Cabin With Amazing Views Of The Hudson River
9.8 out of 10, Exceptional, (42 reviews)
"The place was as charming as the pictures, and the views were incredible. We would also recommend the bath/hot tub as well, it was a relaxing and lovely stay!"
United States
Jennifer A.
The price is NZ$355
includes taxes & fees
1 Apr - 2 Apr
Sweet New Cabin With Amazing Views Of The Hudson River
Interior

Holiday Home in Glens Falls

Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
10.0 out of 10, Exceptional, (7 reviews)
"Everything was exactly as advertised, wonderful stay!"
United States
Jim W.
The price is NZ$1,492
includes taxes & fees
9 Mar - 10 Mar
Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
Property grounds

Holiday Home in Lake George

Three Bedroom House Lake George
8.0 out of 10, Very good, (1 review)
"This is a neat, small house, that while a bit dated in decor, was very comfortable and clean for an overnight reunion of "senior" friends from high school. It provided us with the space to sit and reminisce and catch up on each other's lives. There was a nice deck overlooking a small picturesque stream, a large, comfortable living room and an adequate kitchen that met our needs. There is also a pool, which, being late in September was not open, but is a nice bonus in season, as well as an...
United States
Susan T.
The price is NZ$368
includes taxes & fees
12 Mar - 13 Mar
Three Bedroom House Lake George
Dining

Holiday Home in Lake George

Luxurious Lake George Getaway
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful place, host was awesome in all communications. Great place will be back!"
United States
Wayne E.
The price is NZ$1,340
includes taxes & fees
1 Apr - 2 Apr
Luxurious Lake George Getaway
House, 5 Bedrooms | Exterior

Holiday Home in Olmstedville

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
The price is NZ$1,372
includes taxes & fees
10 Mar - 11 Mar
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
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.
View all properties

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area

10/10 Excellent
"We've stayed here before, we ski and it is less then 30 min from the mountain. It is always quiet and clean. The staff is friendly."
Susan 3-night trip
Posted 12 hours ago
Super 8 by Wyndham Lake George/Warrensburg Area

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
311
Accommodation
576 Holiday Homes
Lowest Price
NZ$320
Highest Price
NZ$1,492