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Holiday Homes in Chestertown

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Chestertown and around

Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi
Interior

Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi

The price is €601
includes taxes & fees
20 Aug - 21 Aug
Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi
Room with two double beds, Lake George
1 bedroom, iron/ironing board, bed sheets

Room with two double beds, Lake George

7.0 out of 10, Good, (2)
"Loved everything about my stay. Will stay here whenever I'm in the area. The care of the staff goes well beyond what is required!"
The price is €108
includes taxes & fees
7 Sept - 8 Sept
Room with two double beds, Lake George
The Bond Inn Room #1
Interior

The Bond Inn Room #1

10.0 out of 10, Exceptional, (2)
"Quite, clean and nice having restaurant and tavern on one property."
The Bond Inn Room #1
Adirondack Bungalow Getaway
Exterior

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (58)
"Had a wonderful stay at this property. Owner was friendly and readily available. Easy to get to and good proximity to ski area. "
Adirondack Bungalow Getaway
Maple Leaf Lodge- Deluxe Suite 2
Exterior

Maple Leaf Lodge- Deluxe Suite 2

10.0 out of 10, Exceptional, (1)
"I booked through Expedia (VRBO) and the room we were assigned was incorrect due to a mistake by the booking sight ( we were assigned a 1 bedroom instead of a two bedroom). The owner had us in a new unit at no extra charge ($100/night difference) within 5 minutes. Awesome customer service!!!"
The price is €180
includes taxes & fees
17 Aug - 18 Aug
Maple Leaf Lodge- Deluxe Suite 2
Charming 1-bedroom hotel with AC and WiFi in wonderful Lake George
1 bedroom, iron/ironing board, WiFi, bed sheets

Charming 1-bedroom hotel with AC and WiFi in wonderful Lake George

Charming 1-bedroom hotel with AC and WiFi in wonderful Lake George
QUEEN ROOM IN LAKE GEORGE-1
Property grounds

QUEEN ROOM IN LAKE GEORGE-1

9.0 out of 10, Wonderful, (2)
"Perfect for a night at Lake George. Walking distance from everything, nice pool and there was a cool waterfall behind our room which made a beautiful, relaxing sound."
The price is €89
includes taxes & fees
7 Sept - 8 Sept
QUEEN ROOM IN LAKE GEORGE-1
Maple Leaf Lodge- Deluxe Suite 3
A heated pool

Maple Leaf Lodge- Deluxe Suite 3

8.0 out of 10, Very good, (1)
"The Unit wasnt exactly as specified, but the Establishment and the Owner of the rental made it satisfying with their quick response time and helpfulness!"
The price is €180
includes taxes & fees
17 Aug - 18 Aug
Maple Leaf Lodge- Deluxe Suite 3
Room 103 king bed .
A heated pool

Room 103 king bed .

10.0 out of 10, Exceptional, (1)
"Clean cozy , had essentials we needed in the morning. Close to all we wanted to do while in the area"
The price is €148
includes taxes & fees
24 Aug - 25 Aug
Room 103 king bed .
Hideaway Lodge - Glen Lake, Lake George
Property grounds

Hideaway Lodge - Glen Lake, Lake George

9.4 out of 10, Exceptional, (13)
"We enjoyed staying at the hideaway lodge and enjoyed the quiet isolation combined with the ease of access to the surrounding area. Hope to stay again in the future!"
The price is €1,573
includes taxes & fees
20 Aug - 21 Aug
Hideaway Lodge - Glen Lake, Lake George
Maple Leaf Lodge- Privacy Cabin 113
Dining

Maple Leaf Lodge- Privacy Cabin 113

The price is €169
includes taxes & fees
17 Aug - 18 Aug
Maple Leaf Lodge- Privacy Cabin 113
Lakeview Lodge|Hot Tub|9 Beds|Pet Friendly|Dock Slip|Lake Views|
Property grounds

Lakeview Lodge|Hot Tub|9 Beds|Pet Friendly|Dock Slip|Lake Views|

2.0 star property
Lakeview Lodge|Hot Tub|9 Beds|Pet Friendly|Dock Slip|Lake Views|
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Terrace/patio

True Adirondack living. 3-bedroom house in tranquil Diamond Point.

10.0 out of 10, Exceptional, (2)
"Beautiful house with so many things to do- enjoy the deck outside, walk to the lake, ping pong or pool in the basement, enjoy time with friends. We will definitely come back! "
The price is €763
includes taxes & fees
16 Aug - 17 Aug
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Gore Mountain Lift View: Wade St. Apt 2
Exterior

Gore Mountain Lift View: Wade St. Apt 2

9.4 out of 10, Exceptional, (12)
"Have stayed here last year, will stay again. Clean, comfortable beds, close to what you want to do. Overall a good place to stay."
Gore Mountain Lift View: Wade St. Apt 2
Spacious 4 bedroom home, close to hiking trails and Gore mountain for skiing
Fridge, microwave, oven, stovetop

Spacious 4 bedroom home, close to hiking trails and Gore mountain for skiing

10.0 out of 10, Exceptional, (2)
"Lovely home with everything you need to sit back and relax. Very clean, close to so many wonderful activities and beach. My family was in town for a wedding on the lake. It was the perfect set up for my adult children and there spouses and my husband and I. We visit our family in the area often and will definitely be booking again. "
Spacious 4 bedroom home, close to hiking trails and Gore mountain for skiing
Vacation Cabin minutes from Lake George w/ Hot Tub
Fridge, microwave, oven, stovetop

Vacation Cabin minutes from Lake George w/ Hot Tub

10.0 out of 10, Exceptional, (9)
"The house is very clean and organized. "
The price is €564
includes taxes & fees
31 Aug - 1 Sept
Vacation Cabin minutes from Lake George w/ Hot Tub
Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
Private kitchen

Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls

10.0 out of 10, Exceptional, (3)
"This is a beautiful apartment in the middle of a fascinating historic downtown area. We enjoyed the shops and restaurants!"
The price is €805
includes taxes & fees
15 Aug - 16 Aug
Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
House, 5 Bedrooms | Interior

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

3.0 star property
The price is €581
includes taxes & fees
25 Aug - 26 Aug
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Gore Mountain Lift View Ski House: Wade St. 1
Property grounds

Gore Mountain Lift View Ski House: Wade St. 1

9.4 out of 10, Exceptional, (19)
"It’s a small wooden vacation home, reasonably equipped (except the oven was not working at our stay). The only down point is the noise from the guests above."
The price is €264
includes taxes & fees
14 Sept - 15 Sept
Gore Mountain Lift View Ski House: Wade St. 1
The Office at North Creek All Season Rental
Games room

The Office at North Creek All Season Rental

9.0 out of 10, Wonderful, (8)
"We had a great stay at The Office rental in North Creek! The location is prime - about 5 minutes from the mountain. Pristine clean with plenty of entertainment for the evening and all the necessaries to warm up a simple breakfast or a quick snack. We had a blast skiing at Gore mountain! Would hardily recommend!"
The Office at North Creek All Season Rental
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

The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"It was 40+ years ago when I stayed at The Georgian. It did not disappoint me at all. I took my two teenage granddaughter and they had a great time. I was only disappointed they they were too young to go out on the kayaks without a parent or guardian."
DENISE 2-night trip
Posted 23 hours ago
The Georgian Lakeside Resort