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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

Exterior
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown
10.0 out of 10, Exceptional, (113)
"Great place to stay for gore mountain, will come again"
United States
Joseph V.
Eagles Nest at Loon Lake near Gore Mountain
Fireplace
Lincoln Log Colony

Lincoln Log Colony

2.0 star property
Lake George
8.8 out of 10, Excellent, (10)
"This is a great property. Initially we rented a large “suite” but immediately upgraded to one of their adorable cabins just across from the playground and pool. The property has super nice and accommodating staff, plenty of parking and really nice families staying there; some are regulars for 20, 40 years! This is truly a family stay place and we were so happy to have found it. Now we’re planning to return year after year! Two beautiful Adirondack chairs on a quiet little stoop outside of each...
United States
Jill
Lincoln Log Colony
Exterior
Terrace on the Lake – Private Lakefront with Breathtaking Views

Terrace on the Lake – Private Lakefront with Breathtaking Views

Warrensburg
10.0 out of 10, Exceptional, (328)
"Everything was excellent and the house is amazing!"
United States
Josh R.
Terrace on the Lake – Private Lakefront with Breathtaking Views
House (2 Bedrooms) | Interior
Waterfront Home on Lake George w/ Boat Dock!

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Queensbury
Waterfront Home on Lake George w/ Boat Dock!
Outdoor dining
ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore

ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore

Warrensburg
9.8 out of 10, Exceptional, (191)
"Amazing property, clean and roomy"
United States
Chris C.
ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore
Dining
Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George

Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George

Warrensburg
9.6 out of 10, Exceptional, (5)
"The three days my friends and I stayed at the cabin was the most fun we’ve had in a while. The house is full of amenities that guarantee you have an amazing stay. From the hot tub to the pool table to even just hanging out by the fire. We had an immaculate stay. The surrounding area has multiple stores and swimming holes including lake George which is a 20 minute drive away. The host couldn’t have been better, Responding within minutes and being very understanding of any issues. Booking this...
United States
Jared M.
Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
Trout House Village Resort

Trout House Village Resort

3.0 star property
Hague
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
The price is ￥22,955
￥29,316 total
includes taxes & fees
Nov 10 - Nov 11
Trout House Village Resort
Property grounds
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Clemons
10.0 out of 10, Exceptional, (100)
"My family and I loved the stay. Great place to enjoy the nature. The house had everything we needed such as great kitchen, fireplace, and jacuzzi. "
United States
Herman K.
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Outdoor spa tub
luxury log home mins from Lake George, w/ heated salt water pool!

luxury log home mins from Lake George, w/ heated salt water pool!

Warrensburg
10.0 out of 10, Exceptional, (168)
"We had the best time with an extended family group from ages 3-65 including my handicapped brother. It’s a great layout for a big group and those with limited mobility with just a few steps up to the house and everything you need on one level. The outside space is amazing and my kids were in the pool and using the playset all day every day! Truly the house had everything you need and the hosts are super nice and responsive. "
United States
Betsy H.
luxury log home mins from Lake George, w/ heated salt water pool!
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Warrensburg
9.8 out of 10, Exceptional, (335)
"We had a great week at this lovely home, something for everyone!The owners were very responsive to our needs!!I would definitely recommend this rental home!"
United States
Pamela L.
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Property grounds
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

North Creek
9.8 out of 10, Exceptional, (102)
"What a beautiful place to stay. The cabin itself is cute and comfortable. The location is awesome."
United States
Dena M.
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin
Property grounds
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

Warrensburg
9.8 out of 10, Exceptional, (49)
"Lots of space, beautiful property. Kids had a blast outside and loved the little loft bedroom outside of our master."
United States
Cassandra W.
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
Interior
Cozy, pet friendly, newly renovated chalet home with shared beach & water views

Cozy, pet friendly, newly renovated chalet home with shared beach & water views

Lake George
9.2 out of 10, Wonderful, (18)
"Had a nice view of the lake, really close to town and neighborhood is quiet"
United States
Ryan B.
Cozy, pet friendly, newly renovated chalet home with shared beach & water views
Exterior
Walk to Million Dollar Beach from this awesome Cottage!

Walk to Million Dollar Beach from this awesome Cottage!

Lake George
10.0 out of 10, Exceptional, (167)
"Property was very clean and was close to downtown and the beaches . Would stay here again"
United States
Lori S.
Walk to Million Dollar Beach from this awesome Cottage!
Outdoor dining
Family Friendly - Pet Friendly

Family Friendly - Pet Friendly

Lake George
9.8 out of 10, Exceptional, (67)
"nice clean cottage, not exactly the two bedroom set up you'd expect "
United States
Anna S.
Family Friendly - Pet Friendly
Exterior
WATERFRONT and AFFORDABLE

WATERFRONT and AFFORDABLE

Warrensburg
8.0 out of 10, Very Good, (32)
"We absolutely loved our stay in the cabins! They were warm and cozy, making for an amazing experience. Being by the river was incredible - falling asleep to the sound of the water was pure bliss. We also had a blast swimming in the lake with the baby. The cabin itself was spotless and very welcoming. Overall, we'd give it a well-deserved 5 out of 5 stars. Can't wait to come back!"
United States
Ruth G.
WATERFRONT and AFFORDABLE
Smart TV, DVD player
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

Bolton
9.6 out of 10, Exceptional, (178)
"Great location! Easy walk to town. Amazing view of the lake. "
United States
Anonymous traveler
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
View from property
Lake George Waterfront Paradise Dock Slip

Lake George Waterfront Paradise Dock Slip

Putnam Station
10.0 out of 10, Exceptional, (4)
"Beautiful house, amazing stay, great views! We enjoyed it!"
United States
Dawid R.
Lake George Waterfront Paradise Dock Slip
Exterior
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Silver Bay
10.0 out of 10, Exceptional, (33)
"We had a great time at this home. The hosts were very welcoming and accommodating- they gave us a heads up about a great fireworks show at silver bay. The property was well maintained with a great kitchen and comfortable beds. I’d highly recommend this for a family stay on Lake George "
United States
Chris D.
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
Property grounds
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

Putnam Station
8.4 out of 10, Very Good, (18)
"The spectacular views from the back porch were amazing. We were in the area for a retirement party so we did not spend as much time at the house as we would have like to. "
United States
Kristin v.
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
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.
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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"The rooms are very spacious and very clean large TV and the rooms and the hallway smelt clean and fresh. The heating was great. The pool is a tad bit cool as previous reviews the doors lock before checkout time and we had to ask to be let back in to get our stuff"
Connie 1-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Lake George

Find out more about Chestertown

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

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?

Terrace on the Lake – Private Lakefront with Breathtaking Views: This vacation home rental near Chestertown 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 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chestertown?

With 58 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.