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Top Holiday Rentals in Chestertown

Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake

9.8 out of 10, Exceptional, (6)
"Our grandkids can’t stop talking about our stay in the Sleepy Hollow cabin. They loved the pool and Loon lake. The evenings around the fire pit were great! A special thanks to Wendy for her hospitality and to Anthony for bringing the marshmallows!"
The price is £331
includes taxes & fees
6 Jul - 7 Jul
Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake

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

The price is £376
includes taxes & fees
29 Jun - 30 Jun
Charming 2-bedroom cabin in welcoming Chestertown with Lake Views and WiFi

Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool

4.0 out of 10, (4)
"Property needs updating especially deck, stairway & musty odor smell."
The price is £595
includes taxes & fees
30 Jun - 1 Jul
Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool

QUEEN ROOM IN LAKE GEORGE-1

The price is £88
includes taxes & fees
7 Jul - 8 Jul
QUEEN ROOM IN LAKE GEORGE-1

Room with Two Double beds Lake George

7.4 out of 10, Good, (3)
"The room was clean, as was the pool area and pool. Check in was easy and super quick. We walked many times into the village of Lake George. Breakfast places were everywhere! Great vacation spot. "
Room with Two Double beds Lake George

Immaculate Rental Houses in Lake George. Full Hotel Amenities. Heated Pool

10.0 out of 10, Exceptional, (2)
"Fine"
The price is £449
includes taxes & fees
1 Jul - 2 Jul
Immaculate Rental Houses in Lake George. Full Hotel Amenities. Heated Pool

Luxurious Lake George Getaway

9.6 out of 10, Exceptional, (5)
"We stayed here for a few days with our family of 3. The house was beautiful and super close to lake George! Our daughter enjoyed using the pool. I would highly recommend it!!"
The price is £1,187
includes taxes & fees
26 Jul - 27 Jul
Luxurious Lake George Getaway

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

10.0 out of 10, Exceptional, (1)
"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 £657
includes taxes & fees
30 Jun - 1 Jul
True Adirondack living. 3-bedroom house in tranquil Diamond Point.

Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.

10.0 out of 10, Exceptional, (22)
"Our stay was perfect. David was an excellent host making me feel welcome and taken care of. "
The price is £544
includes taxes & fees
2 Jul - 3 Jul
Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (53)
"Had a wonderful stay at this property. Owner was friendly and readily available. Easy to get to and good proximity to ski area. "
The price is £184
includes taxes & fees
7 Jul - 8 Jul
Adirondack Bungalow Getaway

Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

9.8 out of 10, Exceptional, (44)
"Great stay, close to Lake George down town. "
The price is £636
includes taxes & fees
29 Jun - 30 Jun
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

3BR Lake Luzerne Retreat with Game Room & Hot Tub

10.0 out of 10, Exceptional, (2)
"We drove from Marquette Michigan and after a very long drive, we entered the house and immediately started relaxing. Even the rain offered some peace and a sense of renewal. The neighborhood was quiet and the views are amazing. We ventured into Queensbury and Glens Falls to check out the stores and places to eat. We were impressed by the friendliness of everyone we encountered. It was very sad when we left, but we would definitely recommend this particular home to friends and family and we look...
The price is £443
includes taxes & fees
17 Jul - 18 Jul
3BR Lake Luzerne Retreat with Game Room & Hot Tub

Vacation Cabin minutes from Lake George w/ Hot Tub

10.0 out of 10, Exceptional, (5)
"The house is very clean and organized. "
The price is £412
includes taxes & fees
30 Jun - 1 Jul
Vacation Cabin minutes from Lake George w/ Hot Tub

Maple Leaf Lodge- Privacy Cabin 113

The price is £144
includes taxes & fees
29 Jun - 30 Jun
Maple Leaf Lodge- Privacy Cabin 113

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 £153
includes taxes & fees
29 Jun - 30 Jun
Maple Leaf Lodge- Deluxe Suite 3

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 £153
includes taxes & fees
29 Jun - 30 Jun
Maple Leaf Lodge- Deluxe Suite 2

Room 104 king bed .

The price is £126
includes taxes & fees
1 Jul - 2 Jul
Room 104 king bed .

Room 108 with two queen beds

The price is £134
includes taxes & fees
20 Jul - 21 Jul
Room 108 with two queen beds

Room 106 two queen beds

The price is £134
includes taxes & fees
1 Jul - 2 Jul
Room 106 two queen beds
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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Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Family Friendly - Pet Friendly : This holiday home rental outside of Chestertown is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Chestertown?

With 60 Expedia holiday rentals, you're guaranteed to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach are other places to visit while you're in town.

What’s a holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.