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Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in Chestertown

Eagles Nest at Loon Lake near Gore Mountain
Exterior

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (111)
"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. "
The price is HK$2,012
HK$5,522 total
includes taxes & fees
7 Sept - 8 Sept
Eagles Nest at Loon Lake near Gore Mountain
Lake George Escape - Campground
2 bedrooms, WiFi

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very good, (166)
"Nice place to staying "
Lake George Escape - Campground
Waterfront Home on Lake George w/ Boat Dock!
Interior

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Property grounds

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

10.0 out of 10, Exceptional, (91)
"Beautiful house! My family and I enjoyed our stay! House was fully stocked with everything you would need! The entire holiday weekend was cold and rainy but we still enjoyed ourselves! We used the hot tub a lot and the heated pool on the first day! The pool was cold on the other 3 days :( But overall we had a great time! "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Outdoor spa tub

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

9.8 out of 10, Exceptional, (189)
"We had a wonderful weekend staying in warrensburg. We had plenty of space to enjoy each others company for a much needed winter retreat . "
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Trout House Village Resort
Living area

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
"Absolutely wonderful place and super friendly staff "
The price is HK$1,116
HK$1,434 total
includes taxes & fees
8 Sept - 9 Sept
Trout House Village Resort
Walk to Million Dollar Beach from this awesome Cottage!
Exterior

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (160)
"Jacki had the place as promised. Neat , clean and organized - tidy .. the charm of the cottage was wonderful !! The location was perfect !! Sleeping was fantastic. Heck we each had our own bathroom!! When we go back we’d definitely stay there again . Oh very quiet , peaceful. Two porches and great fireplace . Thank you Jacki "
Walk to Million Dollar Beach from this awesome Cottage!
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
Exterior

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

10.0 out of 10, Exceptional, (28)
"Everything was perfect. The house is gorgeous and had everything we needed. Love the location too!"
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Exterior

Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay

9.8 out of 10, Exceptional, (114)
"Property was extremely clean and Tom was so helpful since I booked. Would definitely stay here again."
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Housekeeping Cottage - near Lake George & Adirondacks
Property grounds

Housekeeping Cottage - near Lake George & Adirondacks

10.0 out of 10, Exceptional, (39)
"We had a wonderful time at the cottage!! Loved the outdoor firepit that you could cook over, fantastic option. We will definitely be back! 😄"
Housekeeping Cottage - near Lake George & Adirondacks
Little Red Cabin by the Brook- 5m to Waterfall
1 bedroom, free WiFi, bed sheets

Little Red Cabin by the Brook- 5m to Waterfall

9.4 out of 10, Exceptional, (17)
"Would definitely visit again!"
The price is HK$921
HK$2,061 total
includes taxes & fees
4 Sept - 5 Sept
Little Red Cabin by the Brook- 5m to Waterfall
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin
Property grounds

PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

9.8 out of 10, Exceptional, (96)
"Very clean and close to the ski area:"
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin
Family Friendly - Pet Friendly
Outdoor dining

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (64)
"Had a great stay, check in was easy, the house was very clean and a great location to the downtown area and easy nice walking area! Would definitely stay here again!!"
Family Friendly - Pet Friendly
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Outdoor dining

2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!

8.8 out of 10, Excellent, (28)
"Nice house, perfect location just outside of all the craziness. Not too far from it either. Easy access to everything. Would recommend staying again "
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Lakefront home private beach on Schroon Lake
Outdoor dining

Lakefront home private beach on Schroon Lake

9.4 out of 10, Exceptional, (24)
"Enjoyed family time on the lake."
Lakefront home private beach on Schroon Lake
Charming cottage with a cozy, welcoming vibe
Interior

Charming cottage with a cozy, welcoming vibe

7.0 out of 10, Good, (14)
"Perfect place away from the strip, so clean and well taken care of. I'd live there forever honestly."
Charming cottage with a cozy, welcoming vibe
Relaxing Forest Retreat/minutes from Lake George
TV, fireplace, DVD player, table football

Relaxing Forest Retreat/minutes from Lake George

9.8 out of 10, Exceptional, (64)
"The property was fantastic. Clean and very spacious. 6 bedrooms and 4 full bathrooms. There were 12 of us and we never felt like it was crowded. Very big kitchen fully stocked with all utensils, beer/wine glasses, mugs, plates etc. The beds were comfortable. The property was 15 minutes easy drive from the "downtown" Lake George and very straight forward drive. Host were very responsive. Check-in process was smooth. Best part of the property was the front porch with two tables with...
Relaxing Forest Retreat/minutes from Lake George
The Elms Waterfront Cottages
In-room dining

The Elms Waterfront Cottages

2.5 star property
8.4 out of 10, Very good, (16)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
The price is HK$2,542
HK$2,822 total
includes taxes & fees
14 Sept - 15 Sept
The Elms Waterfront Cottages
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Terrace/patio

Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

10.0 out of 10, Exceptional, (92)
"Reunion with old friends. Perfect for us all to have our own bedrooms. Many choices for hang spots, fun games and great huge deck. Owners and host are delightful to communicate with. We will plan to come back!"
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool
Exterior

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 HK$4,676
HK$6,170 total
includes taxes & fees
4 Sept - 5 Sept
Beautiful 4 Bedroom on top of Mountain With Mountain Views and Pool
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

Find out more about Chestertown

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Eagles Nest at Loon Lake near Gore Mountain: This highly rated holiday home rental in Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a pool table.

How many holiday rentals will I find in Chestertown?

With 59 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?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River 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.