Photo by Julie Miller

Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, 39 reviews
"The house is the perfect combination of woodsy and modern. Most of the wooden furniture has been beautifully hand made with creative design. The high celings in the main family room are also made of gorgeous wood. There is a real fireplace that we unfortunately did not use because it was too warm. Comfy leather recliners and a 75 inch TV. The kitchen is open to the main room with a peninsula to sit at with stools. Modern appliances, all the kitchen ware you could possibly need, clean and new....
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, 48 reviews
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
Cozy retreat with fireplace, kayaks, and shared beach/pond access
8.8 out of 10, Excellent, 9 reviews
"We loved the days we stayed there, beautiful environment, very nice view. Be careful with the mosquitos, they came out in the evening."
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Peaceful Lakeside Retreat with Private Beach
9.4 out of 10, Exceptional, 9 reviews
"We stay in Lake George every year for Labor Day. Although we love it, I wanted something more peaceful. This place was amazing. Very clean, quiet and lits to do right there on the property. We ate at George Henry's, the food was fantastic. Its only about a 20 min drive to Lake George, so we got the best of both worlds 😊 Would love to come back again next year!"
Peaceful Lakeside Retreat with Private Beach
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, 64 reviews
"Great views and accommodations"
The price is CA $191
CA $253 total
includes taxes & fees
Jun 16 - Jun 17
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
9.8 out of 10, Exceptional, 96 reviews
"Beautiful waterfront with easy access to paddling, swimming, ping pong, or just relaxing. Loved the deck and firepit."
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, 36 reviews
"Great time awesome fishing cottage was super clean and maintained"
Adirondack Creekside Cottage-Sportmen’s Delight
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, 29 reviews
"Perfect cozy getaway. Peaceful!"
The price is CA $199
CA $261 total
includes taxes & fees
Jun 16 - Jun 17
Handcrafted mountain cabin with gorgeous views
Cottage - near Lake George & Adirondacks - year round
10.0 out of 10, Exceptional, 28 reviews
"Nice people "
Cottage - near Lake George & Adirondacks - year round
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
10.0 out of 10, Exceptional, 281 reviews
"Very nice house. Great location with proximity to lakes & golf & restaurants."
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Get away to the Adirondacks, heated Pool open, hot tub on deck.
10.0 out of 10, Exceptional, 50 reviews
"The pictures don’t do this property justice! We had such a wonderful stay at this property! It was relaxing, and had everything you could need for a weekend away! The weather didn’t cooperate for the pool, but there was plenty of things to do! Would love to stay at this property again"
Get away to the Adirondacks, heated Pool open, hot tub on deck.
Cabin, lake and moose...OH MY!!
10.0 out of 10, Exceptional, 27 reviews
"Host was super responsive. Cabin was brand new and in excellent shape. Very nice, thoughtful decor. Driveway quite steep but doable. Access to the lake is quite a long walk away from the house, as the only drawback. Otherwise a lovely place and would highly recommend!"
The price is CA $378
CA $625 total
includes taxes & fees
Jul 8 - Jul 9
Cabin, lake and moose...OH MY!!
LAKE GEORGE LOG CABIN
9.0 out of 10, Wonderful, 19 reviews
"This cabin was cozy, clean and spacious. We loved the rustic smell and look. Thanks to our host for keeping it so clean. We will definitely come back!"
LAKE GEORGE LOG CABIN
Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!
9.2 out of 10, Wonderful, 83 reviews
"We took a quick trip over April break to see the Solar Eclipse! The house was perfect for our needs. Off season made the area very quiet. We enjoyed our stay"
The price is CA $412
CA $659 total
includes taxes & fees
Jun 22 - Jun 23
Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
9.8 out of 10, Exceptional, 6 reviews
"It's everything you need in a lake house, with plenty of character, lots of space (and steps), and a great view. It's not perfect - living room furniture could use a little refresh, but as a last minute getaway it was great."
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
8.8 out of 10, Excellent, 16 reviews
"The property was in a word: lovely. You can tell a lot of work went into renovating this place. My friend and I absolutely loved just chilling on the front porch each night. We meant to have a fire in the back, but we never got around to it. There was plenty of wood provided though, which was fantastic, as you can't bring firewood from out of state. The pool was a nice addition. The beds were very comfortable. The water was crisp and clean. My only complaint at all was not with the property or...
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Charming cabin with three river-view decks & private setting
9.6 out of 10, Exceptional, 7 reviews
"The cabin is quiet and serene as described. But, please be aware of several things. 1. The “coin laundry” is not on site and the local laundromat hours are limited. 2. There is no foil, Saran Wrap, Tupperware or storage containers for leftovers, zip locks/bags, or cooking oil. Salt and pepper are the only spices on site. There were ten people on our reservation and we ran out of dish soap, toilet paper, and dishwasher soap on the third day. When these items were requested they were denied. The...
The price is CA $218
CA $590 total
includes taxes & fees
Jun 17 - Jun 18
Charming cabin with three river-view decks & private setting
GORGEOUS AND MODERN describes this 6 bedroom home .
8.0 out of 10, Very good, 49 reviews
"Plenty of room for all of us three bathrooms was very nice and accommodating. We had a wedding not far away and worked out great."
GORGEOUS AND MODERN describes this 6 bedroom home .
Beautiful cottage on quiet country road walking distance to charming North Creek
9.8 out of 10, Exceptional, 27 reviews
"Charming little cabin. Well stocked. Little trail down to the river right in front with a pool for the kids to play in. Highly recommend for quick and easy getaway from the capital."
The price is CA $192
CA $254 total
includes taxes & fees
Jun 17 - Jun 18
Beautiful cottage on quiet country road walking distance to charming North Creek
WATERFRONT and AFFORDABLE
8.2 out of 10, Very good, 23 reviews
"Wonderful"
WATERFRONT and AFFORDABLE
Don't see what you're looking for?
See all available properties in Chestertown
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.

Chestertown Vacation Rental Travel Info

Number of vacation rentals
27
Popular accommodation
Chestertown private vacation homes
Known landmarks
Loon Lake Beach, Natural Stone Bridge and Caves and Friends Lake
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Chestertown you may be interested in

La Quinta Inn & Suites by Wyndham Lake George
2.0 star property
9.0 out of 10, Wonderful, 1,265 reviews
"Not thing"
The price is CA $162
CA $180 total
includes taxes & fees
Jun 19 - Jun 20
La Quinta Inn & Suites by Wyndham Lake George
Six Flags Lodge & Indoor Waterpark
3.5 star property
7.8 out of 10, Good, 1,001 reviews
"Water park was great."
The price is CA $275
CA $366 total
includes taxes & fees
Jun 16 - Jun 17
Six Flags Lodge & Indoor Waterpark
The Queensbury Hotel
3.0 star property
9.2 out of 10, Wonderful, 1,136 reviews
"The location was near everything we wanted"
The price is CA $184
CA $204 total
includes taxes & fees
Jun 16 - Jun 17
The Queensbury Hotel
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chestertown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace: You might like this vacation home rental near Chestertown. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Chestertown?

With 60 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.

Recent reviews of Chestertown properties
Expedia verified reviews