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Search Vacation Homes in Chestertown

Compare 394 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
10.0 out of 10, Exceptional, (281)
"The house was perfect for the 9 of us, we did not want to leave Sunday! The kitchen had everything we needed. The space was very nice in a big party. You didn’t feel crowded. The pool was an awesome add on. Saturday afternoon the weather was a perfect temperature so we were able to take advantage! The location is great. Not to close to Lake George but your not in a tourist town. Ubers are available to grab you if you want to go have some drink in town. We have talked about coming back yearly...
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
9.6 out of 10, Exceptional, (145)
"The place is very nice and the view is just amazing. Plenty of space for a bunch of family and/or friends to enjoy. Only downside is the sewer plant being so close to the property. The smell is bit much when the wind is blowing from the pant towards the house. It’s not constant so it’s bearable and the beauty of the house makes up for it. Definitely would go back again."
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
QUEEN ROOM IN LAKE GEORGE
4.0 out of 10, (1)
"Broken AC. Hair dryer had no outlet to connect to. "
The price is $70
$108 total
includes taxes & fees
Jun 10 - Jun 11
QUEEN ROOM IN LAKE GEORGE
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Cozy, pet friendly cabin minutes to lake George village
9.8 out of 10, Exceptional, (13)
"Located less than 7 minutes from downtown Lake George, you find yourself surrounded by a nice quiet setting in the woods. Once you get inside, the living / dinning area is spacious. Enough room for everyone to enjoy themselves. The outside deck has a grill ... and the view of the small creek is great. We are coming back!"
Cozy, pet friendly cabin minutes to lake George village
Top Rated Rental House In The HEART of Lake George Village
Top Rated Rental House In The HEART of Lake George Village
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (48)
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
Bolton Landing - 4 Bdrm Vacation Rental
10.0 out of 10, Exceptional, (2)
"This house is absolutely beautiful, very cozy, and has all the amenities you need. The beds were comfortable, linens spotless, and perfect pillows. The location is ideal, with short trips to Bolton and downtown Lake George. In short, great stay and would definitely go back."
Bolton Landing - 4 Bdrm Vacation Rental
Charming Glens Falls Retreat Near Downtown!
10.0 out of 10, Exceptional, (1)
"Great house for our stay. The place was as dedcribed and would book this again."
Charming Glens Falls Retreat Near Downtown!
Countryside 6-bedroom house centrally located
10.0 out of 10, Exceptional, (1)
"Stay was excellent, spacious. Host easy to communicate with and helpful. Reasonable price."
Countryside 6-bedroom house centrally located
Lake George NY - Family & Pet Friendly Vacation Home
9.4 out of 10, Exceptional, (67)
"Very home like, cozy and comfortable, the owner was very helpful and responsive."
Lake George NY - Family & Pet Friendly Vacation Home
Secluded and Cozy Updated Twin Creeks Cabin
9.8 out of 10, Exceptional, (6)
"We loved the cabin - it was everything we expected and more. The property is deep enough in the woods to feel/be private yet close enough to LG village that there’s always a quick and close attraction to visit. Just great! Can’t wait to return."
Secluded and Cozy Updated Twin Creeks Cabin
This is a beautiful house that sits facing Loon Lake! Amazing views and dock!!!
This is a beautiful house that sits facing Loon Lake! Amazing views and dock!!!
The Porch House - IN TOWN!
10.0 out of 10, Exceptional, (6)
"We loved staying here! The house is very nice, clean, and spacious! Within minutes you can walk to several restaurants/bars and even down to the lake. We would definitely stay there again!"
The Porch House - IN TOWN!
Bolton Hill Lodge
Bolton Hill Lodge
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
9.8 out of 10, Exceptional, (6)
"It's everything you need in a lake house, with plenty of character, lots of space (and steps), and a great view. It's not perfect - living room furniture could use a little refresh, but as a last minute getaway it was great."
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
Get away to the Adirondacks, heated Pool open, hot tub on deck.
10.0 out of 10, Exceptional, (49)
"Hot tub is awesome. Love that it is available year round. Great place to unwind and enjoy with family/friends."
Get away to the Adirondacks, heated Pool open, hot tub on deck.
Charming cabin with three river-view decks & private setting
9.6 out of 10, Exceptional, (7)
"The cabin is quiet and serene as described. But, please be aware of several things. 1. The “coin laundry” is not on site and the local laundromat hours are limited. 2. There is no foil, Saran Wrap, Tupperware or storage containers for leftovers, zip locks/bags, or cooking oil. Salt and pepper are the only spices on site. There were ten people on our reservation and we ran out of dish soap, toilet paper, and dishwasher soap on the third day. When these items were requested they were denied. The...
The price is $159
$427 total
includes taxes & fees
Jun 10 - Jun 11
Charming cabin with three river-view decks & private setting
Hickory Hill Mountaintop charming family friendly quiet very private lake view
10.0 out of 10, Exceptional, (120)
"This home is so beautiful and it was the right place for our family getaway. Very clean and you feel at home as soon as you walked in the door. Kitchen was large and stocked with everything you would need and more. Lots of games and the pool table,ping pong table and foosball, was Soo fun. The owner Joyce was very good at communicating when we had any questions. We made some wonderful family memories. Would definitely stay again."
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Secluded Gore Mountain Pine-Panelled Getaway
9.6 out of 10, Exceptional, (122)
"We had a great time! Home is spacious, located in the woods but sunny. There is everything you need for an enjoyfull stay."
Secluded Gore Mountain Pine-Panelled Getaway
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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.

Other property types in Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (39)
"The house is the perfect combination of woodsy and modern. Most of the wooden furniture has been beautifully hand made with creative design. The high celings in the main family room are also made of gorgeous wood. There is a real fireplace that we unfortunately did not use because it was too warm. Comfy leather recliners and a 75 inch TV. The kitchen is open to the main room with a peninsula to sit at with stools. Modern appliances, all the kitchen ware you could possibly need, clean and new....
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (48)
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
Cozy retreat with fireplace, kayaks, and shared beach/pond access
8.8 out of 10, Excellent, (9)
"We loved the days we stayed there, beautiful environment, very nice view. Be careful with the mosquitos, they came out in the evening."
Cozy retreat with fireplace, kayaks, and shared beach/pond access
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.

Chestertown Vacation Homes information

Number of reviews
767
Accommodation
394 Vacation Homes
Lowest Price
$70
Highest Price
$159

Recent reviews of Chestertown hotels
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