Photo by Julie Miller

Chestertown Vacation Rentals

Vacation Rentals in Chestertown

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
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, (63)
"Beautiful mountain views"
The price is $160
$211 total
includes taxes & fees
May 23 - May 24
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
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
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Property grounds
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
10.0 out of 10, Exceptional, (49)
"Group of 4 adult friends spent 2 nights around the eclipse. It was perfect! Clear communication before and during. Comfy beds, large living areas to hang out, we utilized the ample facilities (3 full bathrooms, fireplace, etc.). Would stay again"
The price is $400
$694 total
includes taxes & fees
May 23 - May 24
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
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
Fridge, microwave, oven, stovetop
Lake George Great Location with Lake Access
10.0 out of 10, Exceptional, (9)
"Since booking our stay, Peter was very helpful and hospitable with our trip to Lake George. Everything from restaurant recommendations to making himself available if we needed anything. The property was VERY clean and comfortable and within a short walk to the water. My girlfriend and I would recommend this property without question. Thank you Peter!"
Lake George Great Location with Lake Access
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
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 $89
$162 total
includes taxes & fees
May 23 - May 24
Adirondack Bungalow Getaway
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
Property grounds
Camp Lillian Gorgeous New Cabin with Mountain Views
10.0 out of 10, Exceptional, (50)
"A beautiful view and relaxing stay!!"
The price is $160
$211 total
includes taxes & fees
May 23 - May 24
Camp Lillian Gorgeous New Cabin with Mountain Views
Fridge, microwave, oven, stovetop
Cabin, lake and moose...OH MY!!
10.0 out of 10, Exceptional, (25)
"Perfect place to stay. Clean and cozy. Thank you ."
The price is $275
$457 total
includes taxes & fees
May 28 - May 29
Cabin, lake and moose...OH MY!!
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
Interior
Log Cabin directly on the lake, within 5-10 minutes away from most attractions!
10.0 out of 10, Exceptional, (1)
"Directly on the lake, you can walk out onto your own private peninsula, fish (I caught two bass in ten minutes), or just enjoy the lounge chairs or couples swing while gazing at the pristine lake or soaking up the fire we made in the brand new fire pit. We slept with the windows open and listened to the waves lapping against the shore right outside. This place was amazing. It had no reviews when we booked it last-minute, which worried us, but it was just great. We were so happy to be there. It...
Log Cabin directly on the lake, within 5-10 minutes away from most attractions!
Property grounds
Private Chalet In NW Bay With 25 Foot Dock!!
10.0 out of 10, Exceptional, (103)
"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!!
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
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
9.8 out of 10, Exceptional, (278)
"Stayed for our friends bachelorette. It was a beautiful home. Master bedroom bed was very load and uncomfortable but other rooms were comfy. The view was amazing. Overall would definitely stay again."
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
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
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
Fridge, microwave, oven, stovetop
Charming cabin with three river-view decks & private setting
9.8 out of 10, Exceptional, (6)
"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 $131
$364 total
includes taxes & fees
May 23 - May 24
Charming cabin with three river-view decks & private setting
Exterior
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, (29)
"Perfect cozy getaway. Peaceful!"
The price is $160
$211 total
includes taxes & fees
May 23 - May 24
Handcrafted mountain cabin with gorgeous views
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

Lobby
The Queensbury Hotel
3.0 star property
9.2 out of 10, Wonderful, (1113)
"We had a lovely meal in one of the 2 restaurants. Our room was on the top floor and was very quiet. There wasn't much room on the left side of bed -- very close to the wall -- I had to scoot toward the foot of the bed in order to clear the small nightstand. The VIP benefit (discount on food/drink) was not properly applied to our bill despite our following the letter given to us at check-in. The clerk at the desk on the morning we checked out said he would take care of the credit and email me a...
The price is $129
$143 total
includes taxes & fees
May 23 - May 24
The Queensbury Hotel
Room, 1 Queen Bed with Sofa bed, Non Smoking, Lake View (Balcony) | Premium bedding, desk, laptop workspace, blackout drapes
Courtyard by Marriott Lake George
3.0 star property
9.2 out of 10, Wonderful, (1000)
"Great people and great clean place. No coffee available until 7am is the only bad part. "
The price is $154
$171 total
includes taxes & fees
Jun 10 - Jun 11
Courtyard by Marriott Lake George
Indoor pool
La Quinta Inn & Suites by Wyndham Lake George
2.0 star property
9.0 out of 10, Wonderful, (1220)
"Hotel was very clean and modern Breakfast was buffet and it was as good as that can be , got to love them waffles , Person in charge of breakfast was well organized and kept it all moving Indoor Pool is nice , particularly for kids "
The price is $93
$103 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.

Everything you need to know about Chestertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

5/5 Excellent
Lake George dance weekend
"Hotel was very clean and modern Breakfast was buffet and it was as good as that can be , got to love them waffles , Person in charge of breakfast was well organized and kept it all moving Indoor Pool is nice , particularly for kids "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Lake George
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Lake George