Photo by Julie Miller

Holiday Rentals in Chestertown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (62)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

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, (155)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!

Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

2.0 out of 10, (1)
"Prior to booking this property I asked questions that were not addressed in the listing. (Currently updated).To Host: "please answer a few questions. Is the room on ground level? How many occupied units are in this building? Is the room located in a quiet location? Is parking onsite? Is it located in a low crime neighborhood?" Host reply: "It’s a 2 apartment building. And yes t Yes to all your other concerns" UPON ARRIVAL, in the front yard there was a soiled mattress leaning against a tree,...
The price is €257
includes taxes & fees
13 Jul - 14 Jul
Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

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 €259
includes taxes & fees
21 Jul - 22 Jul
Trout House Village Resort

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

8.8 out of 10, Excellent, (26)
"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!

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

10.0 out of 10, Exceptional, (5)
"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 €184
includes taxes & fees
16 Jul - 17 Jul
Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

Cozy Private Lake Cabin Minutes to Lake George & Saratoga Springs - Pet Friendly

9.2 out of 10, Wonderful, (19)
"The cozy lake house was just the get away we needed. There was so many activities including swimming, fishing kayaking, paddle board/boat. Close to lake gorge, great little deli near by!"
Cozy Private Lake Cabin Minutes to Lake George & Saratoga Springs - Pet Friendly

Family Friendly - Pet Friendly

9.6 out of 10, Exceptional, (53)
"Had a great time and was perfect for our family! "
Family Friendly - Pet Friendly

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 €344
includes taxes & fees
13 Jul - 14 Jul
The Elms Waterfront Cottages

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (60)
"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

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

9.8 out of 10, Exceptional, (112)
"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

Bolton Landing - walk to town! Come visit any Season!

10.0 out of 10, Exceptional, (51)
"Such a great stay. Everything was clean and the location was perfect. The communication was also fantastic…will stay here again!"
Bolton Landing - walk to town! Come visit any Season!

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 €1,096
includes taxes & fees
31 Jul - 1 Aug
Lake George Water Front Cabin Spectacular Views

Terrace on the Lake – Private Lakefront with Breathtaking Views

10.0 out of 10, Exceptional, (312)
"This was the best weekend and the best accomodations! It was incredibly clean and we were all comfortable. They had everything we needed and more. "
Terrace on the Lake – Private Lakefront with Breathtaking Views

Bear Cub Barn, Bolton Landing

Bear Cub Barn, Bolton Landing

Breathtaking Mountain Views Surround New Lakefront Condo

9.8 out of 10, Exceptional, (90)
"Beautiful location will definitely be booking it next year. The staff was amazing."
Breathtaking Mountain Views Surround New Lakefront Condo

Camp Lillian Gorgeous New Cabin with Mountain Views

9.8 out of 10, Exceptional, (68)
"The Lillian cabin was great!! It was not only beautifully made but it had everything we needed including a peaceful and quiet two nights in the Adirondacks!!"
The price is €216
includes taxes & fees
31 Jul - 1 Aug
Camp Lillian Gorgeous New Cabin with Mountain Views

Lake view , Cozy One Bedroom! Walk to Beach and Town!

10.0 out of 10, Exceptional, (46)
"Great stay, convenient location and walk to town, quite and clean"
Lake view , Cozy One Bedroom! Walk to Beach and Town!

Mountain-view house with wood-burning fireplace, deck, patio, & washer/dryer

8.4 out of 10, Very good, (7)
"We had a great time at this house. The location was perfect for us. Close to skiing, restaurants and Lake George is 20 minutes away. The house had everything we needed. Very clean, great amenities, plenty of room and we enjoyed relaxing near the wood stove. "
Mountain-view house with wood-burning fireplace, deck, patio, & washer/dryer
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Family Friendly - Pet Friendly : This holiday home rental outside of Chestertown is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Chestertown?

With 63 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.