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Search Vacation Homes in Chestertown

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Compare 409 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

10.0 out of 10, Exceptional, (301)
"Beautiful log home in a quiet neighborhood right on the river. Such a nice home. Highly recommend you stay here. Great for large family gatherings. "
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Terrace on the Lake, Spectacular Large Home with Private Beach

10.0 out of 10, Exceptional, (301)
"The space is great for a family gathering. Spacious shared spaces and comfortable bedrooms. "
Terrace on the Lake, Spectacular Large Home with Private Beach

Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

9.6 out of 10, Exceptional, (41)
"Amazing view from the back deck, very clean home, plenty of room for our family of 6. Will definitely be staying here again next time we're in Lake George!"
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

Cozy, pet friendly cabin minutes to lake George village

8.8 out of 10, Excellent, (20)
"Excellent location! Minutes to restaurants and shops! Very nice rental! "
Cozy, pet friendly cabin minutes to lake George village

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

10.0 out of 10, Exceptional, (69)
"We were looking for something for our “baby moon” before I go back to work. We had a dream checklist and this home checked off everything on our list. We brought our 3mo old and our dog and had a peaceful weekend enjoying the hot tub, the Blackstone, and the cozy fireplace. We had some questions that were answered immediately. Can’t wait to go back with friends when it’s warmer not enjoy the pool and yard more! Love love lovd"
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

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

10.0 out of 10, Exceptional, (153)
"Our group of friends had a great time at this house. Very clean and well stocked and beautiful property. Ate at Bandstand Brew Works a couple times which was amazing. Played volleyball, used the hot tub, sat around the fire pit. Host was really responsive. Would definitely stay again!"
luxury log home mins from Lake George, w/ heated salt water pool!

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

9.6 out of 10, Exceptional, (155)
"Fantastic!! Cozy!!! gorgeous views! The whole experience was wonderful. Cannot wait to go back. Owner was very responsive!"
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

Waterfront 5BR Home with Dock Slip

10.0 out of 10, Exceptional, (22)
"The house is even better in person. So many beautiful amenities and we really enjoyed having a small shallow area to swim in. Ducks would often come right up to the dock. Beautiful firepit and grill area. Very accommodating host. We rented a boat and loved having a dock to keep it at overnight. It was a perfect house for a family vacation!"
Waterfront 5BR Home with Dock Slip

Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D

10.0 out of 10, Exceptional, (3)
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D

Lakefront luxury, Lake George log cabin home with your own private sandy beach

9.8 out of 10, Exceptional, (13)
"Wonderful trip with friends for our annual kid free weekend! Excellent location with beautiful views! Great location and close enough to village for easy access to restaurants and shopping. "
Lakefront luxury, Lake George log cabin home with your own private sandy beach

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (40)
"Perfect place and location to explore the Adirondacks. Warrensburg is a great little town with friendly folks. Home is comfortable and dog friendly. "
The price is AED 400
AED 681 total
includes taxes & fees
24 Nov - 25 Nov
Adirondack Bungalow Getaway

2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C

9.6 out of 10, Exceptional, (12)
"The location was great for our motorcycle rides around the Adirondacks."
2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C

TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!

10.0 out of 10, Exceptional, (101)
"My friends and I enjoyed our stay at Tripp Lake Retreat. The house feels like a home away from home, nestled in the trees with a view of the lake. Fall is a lovely time to be here and relax with friends. Short walks on crisp mornings, drives to local craft stores and relaxing by the fire made the trip just what we wanted for our time together. Debbie is a gracious host and responsive to needs. I will definitely consider staying again as Tripp Lake Retreat becomes a favorite spot."
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!

Picturesque Family Getaway: Close to Beach ~ Yard!

10.0 out of 10, Exceptional, (18)
"The property was easy to find, plenty of driveway space for parking, quiet and comfortable. I will be a return visitor."
Picturesque Family Getaway: Close to Beach ~ Yard!

The Alexander House 1887 Farmhouse in North Creek!

10.0 out of 10, Exceptional, (37)
"Had a great time in North Creek. The house was a quick walk into the village. Chris and Christen were great hosts. Beds were great, house was warm. All-in-all a fantastic weekend!"
The Alexander House 1887 Farmhouse in North Creek!

The Office at North Creek All Season Rental

9.6 out of 10, Exceptional, (4)
"Good open space with fun amenities. Laundry facilities included but located in bedroom. An oven and toaster were listed as amenities, but was actually a toaster/oven."
The price is AED 334
AED 889 total
includes taxes & fees
26 Nov - 27 Nov
The Office at North Creek All Season Rental

NEW for 2024, 6 person hot tub. Spacious country home with large back yard.

10.0 out of 10, Exceptional, (10)
"My husband and I and another couple usually go away every October. We decided to check out the Lake George area and surrounding Adirondacks. Good location for access to different parts of the Adirondacks. We really enjoyed our stay. The house is beautiful and the surrounding area. "
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.

Serene Loon Lake Waterfront - Sleeps up to 10

10.0 out of 10, Exceptional, (3)
"If you are looking for a lake front property, enjoy being on the lake with your family this is the perfect house. You get the peacefulness of the lake with a short drive to Lake George."
Serene Loon Lake Waterfront - Sleeps up to 10

Luxury Fall Retreat with mountain views - 10 min to Lake George

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great clean house! Perfect for a family of 4-6. Close to everything Lake George has to offer. Would definitely stay here again!"
Luxury Fall Retreat with mountain views - 10 min to Lake George

Family Friendly- Pet Friendly

9.4 out of 10, Exceptional, (36)
"This place is spotless, gorgeous, cozy and close to everything. We used the grill right outside our front door. Parking was literally 5 feet from the front door. Weather was perfection. Sat on our deck for evening cocktail hour. Truly a gem of a spot. We can't say enough good things. It's spectacular. Don't hesitate to book"
Family Friendly- Pet Friendly
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

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access

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

10.0 out of 10, Exceptional, (53)
"Host John was like best of friends. Couldn’t have done more for us. Sue too was very nice. Pearl and ruby, their do"
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.