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Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

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, (159)
"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 €345
includes taxes & fees
18 Aug - 19 Aug
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

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

8.8 out of 10, Excellent, (27)
"We thought the property was nicely decorated. Everything was functional and a good condition. At the time of the year we were going the pool was not an issue."
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

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

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 €182
includes taxes & fees
18 Aug - 19 Aug
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 €1,003
includes taxes & fees
2 Sept - 3 Sept
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)
"This was a great little getaway. Would definitely come back. "
The price is €240
includes taxes & fees
13 Aug - 14 Aug
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 €231
includes taxes & fees
10 Aug - 11 Aug
Little Red Cabin by the Brook- 5m to Waterfall

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

10.0 out of 10, Exceptional, (321)
"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, (54)
"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

Housekeeping Cottage - near Lake George & Adirondacks

10.0 out of 10, Exceptional, (36)
"This was perfect for my family."
Housekeeping Cottage - near Lake George & Adirondacks
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?

RUSTIC COUNTRY COTTAGE With SWIMMING POOL: This holiday home rental outside of Chestertown is located in the mountains, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and an arcade/games room so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chestertown?

With 62 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.