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Vacation Homes in Chestertown

Terrace on the Lake – Private Lakefront with Breathtaking Views

10.0 out of 10, Exceptional, (321)
"this house is setup extremely well, especially for multiple couples. "
Terrace on the Lake – Private Lakefront with Breathtaking Views

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

10.0 out of 10, Exceptional, (96)
"Beautiful house and perfect for our group!"
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Family Friendly - Pet Friendly

9.6 out of 10, Exceptional, (61)
"The only issue I have is, we were told is was only a mile from the lake but it was way more than that."
Family Friendly - Pet Friendly

Lake George Waterfront Paradise Dock Slip

10.0 out of 10, Exceptional, (2)
"Beautiful house, amazing stay, great views! We enjoyed it!"
Lake George Waterfront Paradise Dock Slip

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

10.0 out of 10, Exceptional, (165)
"We had the best time with an extended family group from ages 3-65 including my handicapped brother. It’s a great layout for a big group and those with limited mobility with just a few steps up to the house and everything you need on one level. The outside space is amazing and my kids were in the pool and using the playset all day every day! Truly the house had everything you need and the hosts are super nice and responsive. "
luxury log home mins from Lake George, w/ heated salt water pool!

Lakefront house in the town of Bolton right on the water with private dock space

10.0 out of 10, Exceptional, (35)
"The view was very enjoyable. Weather permitting, we sat on the front porch or the sun chairs. The house is right ON THE WATER. There is plenty of room in the house. The boat dock was easy to get in and out of also. The owners were very nice and got back to me right away. "
Lakefront house in the town of Bolton right on the water with private dock space

Cozy, pet friendly, newly renovated chalet home with shared beach & water views

9.0 out of 10, Wonderful, (16)
"Had a nice view of the lake, really close to town and neighborhood is quiet"
Cozy, pet friendly, newly renovated chalet home with shared beach & water views

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

10.0 out of 10, Exceptional, (3)
"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.

RUSTIC COUNTRY COTTAGE With SWIMMING POOL

7.6 out of 10, Good, (24)
"Perfect for family to gather and perfect place with alot of option for outdoor activities 🤗"
RUSTIC COUNTRY COTTAGE With SWIMMING POOL

Lakefront home private beach on Schroon Lake

9.2 out of 10, Wonderful, (26)
"Brown’s Beach home worked well for our family of 11. It was very clean & had all new appliances. We loved that each bedroom on 1st level had its own separate bathroom. Driveway is a bit challenging Lorraine was very attentive to anything we needed & her staff was very nice. Schroon Lake water is so clear! Beautiful area!"
Lakefront home private beach on Schroon Lake

Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

9.6 out of 10, Exceptional, (175)
"Family vacation . 6 adults 2 kids. Absolutely gorgeous location. You have beautiful mountain all to yourself . Then can walk to the town in a few minutes with great restaurants . So total privacy but then short walk to town. Beds comfortable. If I could give more than 5 stars I would. "
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

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

9.8 out of 10, Exceptional, (150)
"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

Vacation Home with 8 beds & fast WiFi with view of the Adirondacks & Lake George

9.8 out of 10, Exceptional, (7)
Vacation Home with 8 beds & fast WiFi with view of the Adirondacks & Lake George

Adirondack Lakefront home with private dock

9.8 out of 10, Exceptional, (23)
"Everything was great, lots of things to do at the house and close by. "
Adirondack Lakefront home with private dock

Adirondack Home on Lake Snow

10.0 out of 10, Exceptional, (5)
Adirondack Home on Lake Snow

Cozy 3 bedroom house

8.8 out of 10, Excellent, (16)
"A very nice clean house with ample parking and a large yard. One suggestion for the owner is to clarify what type of coffee maker is provided, as we bought ground coffee with us but it is a Keurig. Alternatively providing the Keurig pods and a salt and pepper shaker would be ideal.. "
Cozy 3 bedroom house

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

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (65)
"Absolutely loved this spot. Easy walk down to the beach and convenient to town. Check in process went flawless and the place was in great condition. We did have to reach out to the property team while we were there and they were super responsive. "
Family Friendly - Pet Friendly

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

9.8 out of 10, Exceptional, (191)
"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

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (112)
"This is the second time that our family has stayed at Eagle's Nest. We enjoyed our time together once again. We had plenty of room and the fire pit, game room and games, sand box and canoes/kayaks were a welcome addition once again. We love the area and this home accommodates our family nicely."
Eagles Nest at Loon Lake near Gore Mountain
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

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Chestertown Vacation Homes information

Number of reviews
1,374
Accommodation
646 Vacation Homes
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