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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 410 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Adirondack Bungalow Getaway
Exterior

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (48)
"The house was very cute. We enjoyed our stay. "
The price is AED 360
AED 597 total
includes taxes & fees
26 Feb - 27 Feb
Adirondack Bungalow Getaway
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Relax in the 7 person hot tub

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

9.8 out of 10, Exceptional, (180)
"12 of us stayed here for a weekend ski trip to Gore. The houses spacious and has a great basement are with tons of fun things for the kids! The hot tub was also a huge hit (even in 10’degree weather!) The home was clean and Charlie was very accommodating and easy to deal with. Will be back!"
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
Lake front

Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.

10.0 out of 10, Exceptional, (37)
"We stayed Aug 17-24. Even with the weather being not so great we had a great time. The house has everything you need. It was spotless and very comfortable. We managed to get in a few games of Cornhole and enjoyed the fire pit at night. My daughters went out in the canoe. It’s a beautiful spot on the lake with a nice little beach and dock. My nephew caught a nice size fish right off the dock. Amy was so nice and very accommodating. We had no issues on our trip at all. "
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Facing the water

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

9.8 out of 10, Exceptional, (310)
"We rented the house for a weekend to accomodate a large group and the house was perfect for that purpose. The home was clean and we woke up to amazing mountain and river views. The common areas were spacious and the kitchen was large and had everything we needed for a fun weekend. The only draw back to the house was that you can hear the people walking above you from the upstairs or the main floor which can make for an early rising in the AM. Other than that the home is perfect and I highly...
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
Front side of house as viewed from large private driveway

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

9.6 out of 10, Exceptional, (160)
"Actually had more room than I thought, we could have fit another 2 people in there! Very spacious. Photos on the website are a little outdated since the TVs have been upgraded since. There were some questionable items like piles of sheets on the floor that looked like they where not cleaned or doors to the closets that where falling off. The master bed rooms remote to the tv was no where to be found so didn't get to use that. But the communication with the host was great. Our safety of making it...
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village.

Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village.

10.0 out of 10, Exceptional, (194)
"I can’t say enough good things about this house as well as the hosts!! The pictures do not do the home justice, it’s just beautiful inside and out. The hosts were more than accommodating for our stay! They gave us great restaurant recommendations along with plenty of things to do in the area , but honestly the house is so cozy and perfect there’s no need to leave! We loved the wood burning stoves and the kids had an absolute blast with the game room and hot tub! The house was super clean and had...
Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village.
Home on the Hudson near Gore and with two baths
View of the Hudson from dining area

Home on the Hudson near Gore and with two baths

10.0 out of 10, Exceptional, (88)
"everything we needed"
Home on the Hudson near Gore and with two baths
Family Gem: Private Community Beach on Tripp Lake
Chestertown Vacation Rental | 3BR | 3.5BA | 3 Steps to Enter | 2,800 Sq Ft

Family Gem: Private Community Beach on Tripp Lake

2.0 star property
9.4 out of 10, Exceptional, (3)
"Property is very clean, well laid out and very spacious for a group of 8 people. The kitchen is well equipped with all the utensils you need for cooking. The owners were very responsive and easy to reach. You have good internet at the property but may not have cellular signal. The mattress were a little soft, specially in the basement. If you prefer firm mattress you may have issues. The other thing to consider is to read the fine print- bring your own towels and bedsheets. We had to go to a...
Family Gem: Private Community Beach on Tripp Lake
The Alexander Barn - Brand new!
Outdoor fire pit with lots of wood !

The Alexander Barn - Brand new!

10.0 out of 10, Exceptional, (2)
"As a family traveling in from Cleveland, Ohio, we were thrilled to return to Gore Mountain, where we used to ski in the early 2000s. Not only were we impressed by the new amenities the mountain has added since then, but this property provided the perfect base for our trip. It’s clear the owners put incredible thought and care into creating a space that’s both luxurious and welcoming. We typically travel and stay at JW Marriott / Ritz Carlton / Waldorf brand hotels, and this is on par with the...
The Alexander Barn - Brand new!
Terrace on the Lake, Spectacular Large Home with Private Beach
Exterior

Terrace on the Lake, Spectacular Large Home with Private Beach

10.0 out of 10, Exceptional, (305)
"We stayed at Terrace on the Lake with several friends and their families and had a great time! The house was clean and had everything we needed--including space for the kids to play. Since it was winter we also appreciated the proximity to Gore Mountain. "
Terrace on the Lake, Spectacular Large Home with Private Beach
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Enjoy sitting in hot tub , enjoying quiet country views.

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

10.0 out of 10, Exceptional, (75)
"My family and I loved the stay. Great place to enjoy the nature. The house had everything we needed such as great kitchen, fireplace, and jacuzzi. "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"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. "
Eagles Nest at Loon Lake near Gore Mountain
luxury log home mins from Lake George, w/ heated salt water pool!
Pool

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

10.0 out of 10, Exceptional, (156)
"We stayed at the property with our family and two other families. We have nine kids ages 4-14 between the three families. The adults and kids LOVED the house. The game room kept the kids entertained all weekend. They enjoyed the bunk bed rooms as well. The house was so clean as was the hot tub. The hosts provided the basics like toilet paper, soap and other toiletries in case we forgot. Towels for showers and the hot tub were provided as well. I would definitely recommend this property to...
luxury log home mins from Lake George, w/ heated salt water pool!
Bolton Landing Compound|Personal Dock Slip|Hot Tub
Property grounds

Bolton Landing Compound|Personal Dock Slip|Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (2)
"This home was absolutely amazing. It accommodated our large group of 12 very comfortably. All the amenities and activities made our stay even more memorable. Great home for winter ski trips. Every detail was well thought out and kept with the theme. We will be coming back! Thank you James and the Lake George Vacay team."
Bolton Landing Compound|Personal Dock Slip|Hot Tub
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Property grounds

Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

9.8 out of 10, Exceptional, (83)
"This cabin had a large floor plan with lots of space for our family to gather. Large dining table for meals and board games, lots of seating around the fireplace and tv area. The bedrooms were all good size and accommodated four adults and teens. The cabin had everything we needed to cook meals. The owner was very friendly, accommodating and responsive."
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Secluded Gore Mountain Pine-Panelled Getaway
Snowy Morning

Secluded Gore Mountain Pine-Panelled Getaway

9.6 out of 10, Exceptional, (131)
"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
5 Bedroom House Lake George Views and Beach Access
Exterior

5 Bedroom House Lake George Views and Beach Access

8.6 out of 10, Excellent, (7)
"Clean, good management, lots of different activities right outside the door. Family friendly. Dog friendly with a nice, short wooded walking path so they could stretch their legs. Beach access does not allow dogs. Kitchen pots/pans/etc are working condition but could use a refresh - my family loves to cook and bake on vacation. We will return! "
5 Bedroom House Lake George Views and Beach Access
North Creek Chalet w/ Fire Pit Near Gore Mountain!
North Creek Vacation Rental | 3BR | 2BA | 1,800 Sq Ft | 2 Stories

North Creek Chalet w/ Fire Pit Near Gore Mountain!

10.0 out of 10, Exceptional, (32)
"Rental was everything as advertised.Very CLEAN "
North Creek Chalet w/ Fire Pit Near Gore Mountain!
Family-Friendly Home w/ Hot Tub, Near Lake George!
Warrensburg Vacation Rental | 3BR | 2BA | 1,397 Sq Ft | Stairs Required

Family-Friendly Home w/ Hot Tub, Near Lake George!

10.0 out of 10, Exceptional, (3)
"Everything that I expected"
Family-Friendly Home w/ Hot Tub, Near Lake George!
Dog-friendly cottage with a wood stove, washer/dryer, firepit, & large yard

Dog-friendly cottage with a wood stove, washer/dryer, firepit, & large yard

8.4 out of 10, Very Good, (7)
"Comfortable setup and close to the mountain and amenities "
Dog-friendly cottage with a wood stove, washer/dryer, firepit, & large yard
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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Other property types in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"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. "
Eagles Nest at Loon Lake near Gore Mountain
Lakefront cabin with beautiful loft, game room, views, private dock

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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.