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Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Featured Holiday Homes in Chestertown and around

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, (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.
Property grounds

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
Outdoor dining

Family Friendly - Pet Friendly

9.6 out of 10, Exceptional, (61)
"Overall had a positive experience! We were within walking distance to the beach and had access to amenities like a fire pit, washer & Dryer and full kitchen. The place was clean & spacious however if you are staying with other families or couples be mindful there is little privacy! It does sleep 6 but the space is all open so unfortunately conversations/snoring/tv will all be heard no matter what room you are staying in. "
Family Friendly - Pet Friendly
Lake George Waterfront Paradise Dock Slip
View from property

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!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (165)
"Very relaxing property and surrounding area"
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
Exterior

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
Interior

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.
Outdoor dining

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
Exterior detail

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
Outdoor dining

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
Smart TV, DVD player

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
Lake

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
Interior

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
Outdoor dining

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
Terrace/patio

Adirondack Home on Lake Snow

10.0 out of 10, Exceptional, (5)
Adirondack Home on Lake Snow
Cozy 3 bedroom house
Interior

Cozy 3 bedroom house

8.8 out of 10, Excellent, (16)
"just a weekend visit here for a graduation party, so we spent very limited time at the rental but we had no issues whatsoever "
Cozy 3 bedroom house
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
Family Friendly - Pet Friendly
Outdoor dining

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
Outdoor spa tub

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

9.8 out of 10, Exceptional, (191)
"The house was amazing and was easily able to accommodate a group in terms of space. The pool and hot tub were very clean and well maintained. We had a great time "
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Eagles Nest at Loon Lake near Gore Mountain
Exterior

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

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"The guy at the check in desk was super polite and welcoming. While the styling of the hotel common areas is a little dated, everything is crisp, clean, and well maintained. The color scheme is pleasant and neutral. (None of those horrid burnt orange and red tones that some hotel chains use.) The room is nice, comfortable, clean, and in good repair. Breakfast was okay, nothing amazing. If I need a room in this area again, I'll definitely return."
Dale 2-night trip
Posted 2 days ago
Baymont by Wyndham Queensbury / Lake George

Find out more about Chestertown

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
1,381
Accommodation
651 Holiday Homes
Lowest Price
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