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Chestertown Holiday Rentals

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Holiday 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 AU$1,186
includes taxes & fees
7 Sept - 8 Sept
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!

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)
"Fantastic stay with all the amenities of home. The house was well equipped and very comfortable. Quiet neighborhood with a large lawn. "
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 AU$530
includes taxes & fees
26 Aug - 27 Aug
The Elms Waterfront Cottages

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.

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, (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

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 AU$283
includes taxes & fees
2 Sept - 3 Sept
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 AU$412
includes taxes & fees
1 Sept - 2 Sept
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!

Hickory Hill Mountaintop charming family friendly quiet very private lake view

10.0 out of 10, Exceptional, (139)
"Beautiful and spacious, clean and very accommodating. Twin beds were a bit narrow and a little uncomfortable, but definitely a great place to stay!!"
Hickory Hill Mountaintop charming family friendly quiet very private lake view
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 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?

Bear Cub Barn, Bolton Landing: This holiday home rental outside of 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 holiday rentals will I find in Chestertown?

With 61 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.