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Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Chestertown

Our top choices for Chestertown holiday homes

West Mt View- 15 min. to Lake George!
Property grounds

West Mt View- 15 min. to Lake George!

10.0 out of 10, Exceptional, (3)
"Great place!"
West Mt View- 15 min. to Lake George!
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, (317)
"Everything was excellent and the house is amazing!"
Terrace on the Lake – Private Lakefront with Breathtaking Views
Family Friendly - Pet Friendly
Outdoor dining

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (64)
"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
Bear Cub Barn, Bolton Landing
Microwave, oven, dishwasher

Bear Cub Barn, Bolton Landing

10.0 out of 10, Exceptional, (2)
"Fantastic stay with all the amenities of home. The house was well equipped and very comfortable. Quiet neighborhood with a large lawn. "
Bear Cub Barn, Bolton Landing
RUSTIC COUNTRY COTTAGE With SWIMMING POOL
Exterior detail

RUSTIC COUNTRY COTTAGE With SWIMMING POOL

8.0 out of 10, Very good, (20)
"Perfect for family to gather and perfect place with alot of option for outdoor activities 🤗"
RUSTIC COUNTRY COTTAGE With SWIMMING POOL
Eagles Nest at Loon Lake near Gore Mountain
Exterior

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (111)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
The price is AU$1,109
includes taxes & fees
7 Sept - 8 Sept
Eagles Nest at Loon Lake near Gore Mountain
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Property grounds

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

10.0 out of 10, Exceptional, (91)
"Beautiful house! My family and I enjoyed our stay! House was fully stocked with everything you would need! The entire holiday weekend was cold and rainy but we still enjoyed ourselves! We used the hot tub a lot and the heated pool on the first day! The pool was cold on the other 3 days :( But overall we had a great time! "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
The Sweet Home in Glens Falls
Exterior

The Sweet Home in Glens Falls

9.0 out of 10, Wonderful, (17)
"Will stay here again. "
The Sweet Home in Glens Falls
Victorian charm with modern conveniences in the heart of Schroon Lake, NY.
Outdoor dining

Victorian charm with modern conveniences in the heart of Schroon Lake, NY.

10.0 out of 10, Exceptional, (2)
"What a fantastic place! Uniquely decorated inside and out, thoughtfully equipped for a family stay, and very close to the town and lake. We loved it!!"
Victorian charm with modern conveniences in the heart of Schroon Lake, NY.
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Outdoor spa tub

Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain

9.8 out of 10, Exceptional, (189)
"We had a wonderful weekend staying in warrensburg. We had plenty of space to enjoy each others company for a much needed winter retreat . "
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Snuggle up in the woods, 7 miles to Lake George,NY
Lake

Snuggle up in the woods, 7 miles to Lake George,NY

9.8 out of 10, Exceptional, (148)
"The cottage was absolutely beautiful and well stocked with anything you needed. We plan on staying yearly "
Snuggle up in the woods, 7 miles to Lake George,NY
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 had a small girls weekend with family. Great place if you looking to just chill, if your looking for shopping, town is small not many stores. Victorian house decorated to time period. We enjoyed ourselves"
The price is AU$823
includes taxes & fees
1 Sept - 2 Sept
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, (29)
"Lovely quaint home with comfy beds and lots of parking. Too bad we reserved during some cold days. Would have love to have jumped in the pool but the fire pit was great"
PET-FRIENDLY - Wonderfully Situated. A Truly Beautiful Setting.
Riverfront home with huge screened deck - dog-friendly, fireplace & fast WiFi
Exterior

Riverfront home with huge screened deck - dog-friendly, fireplace & fast WiFi

8.8 out of 10, Excellent, (16)
"This cabin is a great escape. Tons of amenities, extremely clean, 5 minutes to town, and a great, screened in deck. This was our second time staying and it is an awesome place to stay!"
Riverfront home with huge screened deck - dog-friendly, fireplace & fast WiFi
Cozy Adirondack Retreat sleeps 5, 3 miles to Gore skiing, hiking, rafting
Fridge, microwave, oven, stovetop

Cozy Adirondack Retreat sleeps 5, 3 miles to Gore skiing, hiking, rafting

10.0 out of 10, Exceptional, (9)
"All was great. Would recommend staying there for a quiet weekend getaway. 30 minute drive to Lake George."
Cozy Adirondack Retreat sleeps 5, 3 miles to Gore skiing, hiking, rafting
'Sweet Serenity' Schroon Lake Family Retreat!
TV, fireplace, books

'Sweet Serenity' Schroon Lake Family Retreat!

10.0 out of 10, Exceptional, (1)
"Wonderful. We would definitely come back to this property when visiting the ADK region. "
'Sweet Serenity' Schroon Lake Family Retreat!
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
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Terrace/patio

Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

10.0 out of 10, Exceptional, (91)
"Reunion with old friends. Perfect for us all to have our own bedrooms. Many choices for hang spots, fun games and great huge deck. Owners and host are delightful to communicate with. We will plan to come back!"
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
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, (139)
"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
luxury log home mins from Lake George, w/ heated salt water pool!
Outdoor spa tub

luxury log home mins from Lake George, w/ heated salt water pool!

10.0 out of 10, Exceptional, (163)
"We had a fantastic stay! The house was well equipped for kids and babies - the sound machines & monitors came in handy when the ones we brought with us didn’t work. The host was also very quick to resolve a minor issue that came up. We’d definitely stay again!"
luxury log home mins from Lake George, w/ heated salt water pool!
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.
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Top Chestertown Hotel Reviews

Find out more about Chestertown

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
848
Accommodation
651 Holiday Homes
Lowest Price
AU$823
Highest Price
AU$1,109

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