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Chestertown Vacation Rentals

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Vacation 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
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
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
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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
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 ￥25,157
￥32,547 total
includes taxes & fees
Jun 4 - Jun 5
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
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
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
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!
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
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!
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
Lake George Great Location with Lake Access
Terrace/patio
Lake George Great Location with Lake Access
10.0 out of 10, Exceptional, (9)
"One bedroom apartment with additional futon in bedroom. Perfectly stocked kitchen, upgrade linens, great location on quieter side of lake with private parking, outdoor space and great views. Less than 100' walk to lake edge. Very nice, accommodating owner/manager. We were there for 5 days to celebrate a Birthday and take advantage of boating on the lake and the wonderful variety of restaurants locally. We'll be back!"
Lake George Great Location with Lake Access
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Outdoor dining
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
10.0 out of 10, Exceptional, (79)
"Just what we needed for the sides of our group. Phenomenal views."
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
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)
"Our family booked the chalet for Christmas and the hosts had the place looking very festive which was lovely. The place was exactly what we were after. Mother nature didn’t give us a white Christmas but we loved our stay and Bolton Landing is a gorgeous town. We loved our stay."
Private Chalet In NW Bay With 25 Foot Dock!!
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, (4)
"I really enjoyed staying the place. "
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
Camp Lillian Gorgeous New Cabin with Mountain Views
Property grounds
Camp Lillian Gorgeous New Cabin with Mountain Views
10.0 out of 10, Exceptional, (51)
"Cabin was extremely clean. Had everything you would want at your fingertips. Loved the compact kitchen with all the utensils needed to prepare meals. The bathroom shower had good water pressure & plenty of hot water. Cabin bed was very comfortable & plenty of blankets. Only small disappointment the kindling wood to use in the firepit was too wet to start a fire. Maybe an outside box to cover the wood to keep it dry would help."
The price is ￥25,157
￥32,704 total
includes taxes & fees
Jun 5 - Jun 6
Camp Lillian Gorgeous New Cabin with Mountain Views
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.
Charming cabin with three river-view decks & private setting
Fridge, microwave, oven, stovetop
Charming cabin with three river-view decks & private setting
9.6 out of 10, Exceptional, (7)
"Great location to Gore Mountain, which was our main reason for our trip! Comfortable and lots of space. Beautiful surroundings! Thank you!!"
The price is ￥25,065
￥62,334 total
includes taxes & fees
Jun 2 - Jun 3
Charming cabin with three river-view decks & private setting
Log Cabin on the Hudson
Exterior
Log Cabin on the Hudson
9.8 out of 10, Exceptional, (83)
"Stayed the weekend with a group of friends and had a great time, would recommend"
Log Cabin on the Hudson
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
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

The Queensbury Hotel
Lobby
The Queensbury Hotel
3.0 star property
9.2 out of 10, Wonderful, (1113)
"Very nice property, looks like an older hotel that was recently renovated. The staff were very nice,."
The price is ￥20,283
￥22,516 total
includes taxes & fees
Jun 2 - Jun 3
The Queensbury Hotel
Six Flags Lodge & Indoor Waterpark
Water park
Six Flags Lodge & Indoor Waterpark
3.5 star property
7.6 out of 10, Good, (1005)
"The bathroom in the water park was not the cleanest. "
The price is ￥29,277
￥39,479 total
includes taxes & fees
Jun 2 - Jun 3
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, (1235)
"The hotel room was excellent and the pool is perfect. Breakfast was good. Unfortunately the room next to us had a small dog that kept barking. I think someone should address the customers about their dog. I do t think the dog should be allowed to stay in the room without the owner to keep it quiet. "
The price is ￥18,577
￥20,621 total
includes taxes & fees
Jun 2 - Jun 3
La Quinta Inn & Suites by Wyndham 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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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

Clarion Inn & Suites at the Outlets of Lake George

Clarion Inn & Suites at the Outlets of Lake George

5/5 Excellent
"The breakfast area was clean and always restocked in a timely manor. The gentleman who is in charge of the breakfast are does a fantastic job! "
A verified traveler stayed at Clarion Inn & Suites at the Outlets of Lake George
Posted 1 day ago
Clarion Inn & Suites at the Outlets of Lake George