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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very good, (164)
"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, (314)
"Everything was excellent and the house is amazing!"
Terrace on the Lake – Private Lakefront with Breathtaking Views

Bear Cub Barn, Bolton Landing

10.0 out of 10, Exceptional, (1)
"Exactly as we expected"
Bear Cub Barn, Bolton Landing

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 $427
CA $474 total
includes taxes & fees
Aug 24 - Aug 25
The Elms Waterfront Cottages

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

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

10.0 out of 10, Exceptional, (91)
"I stayed here with friends and it was perfect! The property and lake are amazing. Communication with Debby was extremely easy."
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

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

8.8 out of 10, Excellent, (27)
"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!

RIVERFRONT ADIRONDACK LOG CABIN

9.4 out of 10, Exceptional, (11)
"Very nice and roomy place with river views in Warrensburg! Worked great for our family!"
RIVERFRONT ADIRONDACK LOG CABIN

Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

10.0 out of 10, Exceptional, (6)
"Owners were super helpful and informative. Cabin was the perfect Inbetween for somone who loves camping and someone who doesn’t love camping. "
The price is CA $217
CA $288 total
includes taxes & fees
Aug 14 - Aug 15
Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

Lake George Water Front Cabin Spectacular Views

9.6 out of 10, Exceptional, (30)
"The house was perfect for my family! The teens loved kayaking! The view was absolutely stunning! Wish we could have stayed longer! Will stay again next year!"
The price is CA $757
CA $1,570 total
includes taxes & fees
Sep 3 - Sep 4
Lake George Water Front Cabin Spectacular Views

The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George

9.0 out of 10, Wonderful, (27)
"Quiet cabin/home in walking distance to the lake. If you are looking for a quiet getaway, this is the perfect cabin. Only 20 mins from downtown lake George. I plan on staying here again next year!! "
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George

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

9.8 out of 10, Exceptional, (187)
"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

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

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (87)
"So beautiful place "
The price is CA $261
CA $374 total
includes taxes & fees
Sep 3 - Sep 4
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

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 $364 total
includes taxes & fees
Aug 19 - Aug 20
Little Red Cabin by the Brook- 5m to Waterfall

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

9.8 out of 10, Exceptional, (322)
"Location was easy to get to. The house was beautifully decorated and located right on the water. Kitchen was fully stocked with pots, pans and utensils so it was easy to cook for the whole group! We had a great time staying here :) 10/10"
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Breathtaking Mountain Views Surround New Lakefront Condo

9.8 out of 10, Exceptional, (91)
"Beautiful location will definitely be booking it next year. The staff was amazing."
Breathtaking Mountain Views Surround New Lakefront Condo

Waterfall Gorge-ous Home w 200+ feet of river frontage -10 mi to Lake George

9.4 out of 10, Exceptional, (55)
"My 3 kids and I absolutely loved the spot. The stream in the back of the house was unique and gorgeous, Diane was communicative and pleasant. Highly recommended"
Waterfall Gorge-ous Home w 200+ feet of river frontage -10 mi to Lake George
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?

RUSTIC COUNTRY COTTAGE With SWIMMING POOL: This vacation home rental near Chestertown is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and an arcade game room so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chestertown?

With 62 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.