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Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Fridge, microwave, oven, stovetop
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (38)
"The place was amazing!!! So clean and had everything you need to stay away from home!!! Our do Oliver especially loved playing with Ruby and Pearl!!!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
Exterior
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (48)
"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
Outdoor dining
Cozy retreat with fireplace, kayaks, and shared beach/pond access
8.8 out of 10, Excellent, (9)
"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
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Peaceful Lakeside Retreat with Private Beach
Property grounds
Peaceful Lakeside Retreat with Private Beach
9.4 out of 10, Exceptional, (9)
"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
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, (63)
"Beautiful mountain views"
The price is HK$1,251
HK$1,619 total
includes taxes & fees
3 Jun - 4 Jun
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
9.8 out of 10, Exceptional, (279)
"Beautiful, great location just outside the village of Lake George. Very peaceful and quiet nice family getaway."
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Cottage - near Lake George & Adirondacks - year round
Property grounds
Cottage - near Lake George & Adirondacks - year round
10.0 out of 10, Exceptional, (27)
"Much of the typical Lake George activities were closed since we visited during April, but we were very happy to stay here and will definitely return! It was the perfect space for us two (with extra to fit an additional friend or 2). Owner provided towels, pans, grill, coffee, etc for the stay which is greatly appreciated. It was close distance to anywhere we needed to go for groceries, activities, stores! Sad to go but I look forward to future travels here :)"
Cottage - near Lake George & Adirondacks - year round
Cozy, pet friendly cabin minutes to lake George village
Fridge, microwave, oven, stovetop
Cozy, pet friendly cabin minutes to lake George village
9.8 out of 10, Exceptional, (12)
"Clean, well furnished, nice neighborhood. Great community. Bed was too soft for my wife but everything else was perfect!"
Cozy, pet friendly cabin minutes to lake George village
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Exterior
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
9.8 out of 10, Exceptional, (94)
"We had a lovely stay. The cottage is charming and perfectly appointed. It is comfortable and full of amenities. We wanted a place that was located in a beautiful setting so that we can relax, but close enough to enjoy the attractions of Lake George and beyond and this location fit the bill. Tom was very gracious and responsive. He made sure everything was perfect for our trip. Would love to come back!"
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Adirondack Creekside Cottage-Sportmen’s Delight
Beach
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, (36)
"Great time awesome fishing cottage was super clean and maintained"
Adirondack Creekside Cottage-Sportmen’s Delight
Beautiful cottage on quiet country road walking distance to charming North Creek
Fridge, microwave, oven, stovetop
Beautiful cottage on quiet country road walking distance to charming North Creek
9.6 out of 10, Exceptional, (25)
"Beautifully furnished cottage with all you need for a comfortable overnight. Propane fireplace and a comfortable couch make it a perfect after-ski spot."
The price is HK$1,290
HK$1,673 total
includes taxes & fees
4 Jun - 5 Jun
Beautiful cottage on quiet country road walking distance to charming North Creek
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Outdoor dining
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
8.6 out of 10, Excellent, (15)
"Great Cabin!! Close to ALL."
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Get away to the Adirondacks, heated Pool open, hot tub on deck.
Property grounds
Get away to the Adirondacks, heated Pool open, hot tub on deck.
10.0 out of 10, Exceptional, (49)
"Hot tub is awesome. Love that it is available year round. Great place to unwind and enjoy with family/friends."
Get away to the Adirondacks, heated Pool open, hot tub on deck.
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Exterior
Hickory Hill Mountaintop charming family friendly quiet very private lake view
10.0 out of 10, Exceptional, (120)
"This home is so beautiful and it was the right place for our family getaway. Very clean and you feel at home as soon as you walked in the door. Kitchen was large and stocked with everything you would need and more. Lots of games and the pool table,ping pong table and foosball, was Soo fun. The owner Joyce was very good at communicating when we had any questions. We made some wonderful family memories. Would definitely stay again."
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Handcrafted mountain cabin with gorgeous views
Exterior
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, (29)
"Perfect cozy getaway. Peaceful!"
The price is HK$1,251
HK$1,619 total
includes taxes & fees
3 Jun - 4 Jun
Handcrafted mountain cabin with gorgeous views
Private Chalet In NW Bay With 25 Foot Dock!!
Property grounds
Private Chalet In NW Bay With 25 Foot Dock!!
10.0 out of 10, Exceptional, (104)
"We had a great stay at this property. Everything from being able to dock the boat, sitting on the Adirondack chairs, enjoying the evening air and fishing, to the great location in the house was perfect. We enjoyed evening fires, sunrises in the morning with Coffee and family gatherings around the table for dinner. We enjoyed being able to take our boat to local restaurants for dinner and returning on the lake to this location, enjoying the sunset. The owners were very nice and were available if...
Private Chalet In NW Bay With 25 Foot Dock!!
Adirondack Bungalow Getaway
Exterior
Adirondack Bungalow Getaway
10.0 out of 10, Exceptional, (35)
"Did a quick getaway with my kids. Easy to find, clean with everything we needed. Close to Lake George and other stuff to do. Overall it was a great experience"
The price is HK$852
HK$1,441 total
includes taxes & fees
3 Jun - 4 Jun
Adirondack Bungalow Getaway
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
Beach
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
10.0 out of 10, Exceptional, (5)
"I really enjoyed staying the place. "
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
WATERFRONT and AFFORDABLE
WATERFRONT and AFFORDABLE
8.2 out of 10, Very good, (23)
"Wonderful"
WATERFRONT and AFFORDABLE
SKI TIME! Adirondack Waterfront Log Cabin
Property grounds
SKI TIME! Adirondack Waterfront Log Cabin
9.2 out of 10, Wonderful, (68)
"This was a 5-day, large family, vacation. There were a few minor issues, but nothing we couldn't overcome. We absolutely loved the location. There were a couple of days that we didn't even leave the property. The mosquitos were horribly, horribly bad! We went through a lot of insect spray and tiki torch fuel, but we were prepared for them. Thanks, Lisa"
SKI TIME! Adirondack Waterfront Log Cabin
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.

Other types of properties in Chestertown you may be interested in

Six Flags Lodge & Indoor Waterpark
Water park
Six Flags Lodge & Indoor Waterpark
3.5 star property
7.6 out of 10, Good, (1011)
"The bathroom in the water park was not the cleanest. "
The price is HK$1,486
HK$1,996 total
includes taxes & fees
9 Jun - 10 Jun
Six Flags Lodge & Indoor Waterpark
La Quinta Inn & Suites by Wyndham Lake George
Indoor pool
La Quinta Inn & Suites by Wyndham Lake George
2.0 star property
9.0 out of 10, Wonderful, (1241)
"Clean comfortable accommodations "
The price is HK$924
HK$1,026 total
includes taxes & fees
3 Jun - 4 Jun
La Quinta Inn & Suites by Wyndham Lake George
Best Western of Lake George
Outdoor pool, pool loungers
Best Western of Lake George
2.5 star property
8.2 out of 10, Very good, (1007)
"Hotel very nice located. Very calm, in the nature, but near the shopping centers and the restaurent. A mention for the spa"
The price is HK$776
HK$861 total
includes taxes & fees
10 Jun - 11 Jun
Best Western of 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.

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

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?

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace: This holiday home rental outside Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Chestertown?

With 60 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.

Recent reviews of Chestertown properties
Expedia verified reviews

The Georgian Lakeside Resort

The Georgian Lakeside Resort

5/5 Excellent
"Best place to stay in Lake George!! "
A verified traveller stayed at The Georgian Lakeside Resort
Posted 16 hours ago
The Georgian Lakeside Resort