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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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 CA $415
CA $1,053 total
includes taxes & fees
Sep 7 - Sep 8
Eagles Nest at Loon Lake near Gore Mountain

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (16)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very good, (165)
"Nice place to staying "
Lake George Escape - Campground

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (160)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!

Terrace on the Lake – Private Lakefront with Breathtaking Views

10.0 out of 10, Exceptional, (316)
"Everything was excellent and the house is amazing!"
Terrace on the Lake – Private Lakefront with Breathtaking Views

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (63)
"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

Bear Cub Barn, Bolton Landing

10.0 out of 10, Exceptional, (2)
"Exactly as we expected"
Bear Cub Barn, Bolton Landing

RUSTIC COUNTRY COTTAGE With SWIMMING POOL

8.0 out of 10, Very good, (20)
"Perfect for family to gather and perfect place with alot of option for outdoor activities 🤗"
RUSTIC COUNTRY COTTAGE With SWIMMING POOL

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 CA $428
CA $475 total
includes taxes & fees
Aug 24 - Aug 25
The Elms Waterfront Cottages

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

10.0 out of 10, Exceptional, (91)
"My family and I loved the stay. Great place to enjoy the nature. The house had everything we needed such as great kitchen, fireplace, and jacuzzi. "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

RIVERFRONT ADIRONDACK LOG CABIN

9.4 out of 10, Exceptional, (12)
"Very nice and roomy place with river views in Warrensburg! Worked great for our family!"
RIVERFRONT ADIRONDACK LOG CABIN

Housekeeping Cottage - near Lake George & Adirondacks

10.0 out of 10, Exceptional, (38)
"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

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

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 CA $198
CA $254 total
includes taxes & fees
Aug 24 - Aug 25
Trout House Village Resort

Little Red Cabin by the Brook- 5m to Waterfall

9.4 out of 10, Exceptional, (17)
"Would definitely visit again!"
The price is CA $163
CA $365 total
includes taxes & fees
Sep 1 - Sep 2
Little Red Cabin by the Brook- 5m to Waterfall

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

10.0 out of 10, Exceptional, (91)
"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

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

WATERFRONT and AFFORDABLE

8.0 out of 10, Very good, (29)
"Absolutely 10 stars. Private✔️Pet friendly✔️View ✔️ Remember, It's camping at its finest. Clean, comfortable and enough room for larger family's Highly recommend. Will be returning "
WATERFRONT and AFFORDABLE

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!
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

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

What are some of the best vacation home rentals in Chestertown?

Bear Cub Barn, Bolton Landing: This vacation home near Chestertown is located in a rural location and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, an oven, and a microwave.

How many vacation rentals will I find in Chestertown?

With 61 Expedia vacation rentals, you're sure 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 vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.