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Compare 21 Chalets in Charlestown with updated reviews, rates, and availability.

"We had a lovely weekend ski trip with friends here and everything was excellent. The house was even more beautiful in person than in the photos. Plenty of room in the driveway for lots of cars, had a tricky time connecting the Bluetooth speaker to the projector but our host Eric was very helpful in talking us through how to connect it. Hot tub was hot and worked great all weekend, I was honestly very impressed with how well it was able to maintain its heat in single digit temperatures outside....

A view of the house looking up the driveway after some early season snow.

"This chalet was the perfect retreat for our Vermont getaway! The house is beautifully designed, incredibly relaxing, and comes fully equipped with all the essentials for a comfortable stay. We especially enjoyed the cozy fireplace. We stayed in the king bedroom on the top floor, and the new mattress made for an exceptionally comfortable sleep. The chalet served as our home base for a 4-night stay, allowing us to explore different areas of Vermont with easy day trips. Ludlow itself offers plenty...

"Great place ! Very clean, close to attractions and communication with owner was great ! Can’t wait to come back. "

Enjoy a nice fire while you overlook the Sachem Trail and watch people ski by.

"Stay was perfect"

"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"

AED 2,065 total

includes taxes & fees

26 Nov - 27 Nov

"The home was well appointed with all the amenities and plenty of room for our three families (6 adults and 6 kids). The game room downstairs and open concept living room were awesome and would have been used more often had the weather not been so perfect. The property is truly the star of this place, picturesque mountain views and an amazing fire pit. We will definitely be renting again."

"This is our third year staying at this mountain chalet and we will continue to return in the future! The cleanliness, comforts and location are nothing short of perfect! Thank you for making this beautiful home available for rental. Looking forward to next year!!"

Nestled in the trees yet walkable to Magic's bars, restaurants, and hiking.

"We had a great stay here! The host was very informative and pleasant to work with and the house offered a lot of amenities. Lots of beds which is perfect for a big group. Thank you for hosting us!"

View of house from top of driveway. Dec. 18th, 2020

"House was beautiful, cozy, and clean. We had an issue with the hot tub on the first night with it being cold, but they had someone come out the next morning to get it back running and we were able to use it the second night. House is in a great location. No complaints. Would stay here again."

AED 1,765 total

includes taxes & fees

28 Nov - 29 Nov

"Great location! House had everything we needed. Property owner very flexible. Would definitely rent again!"

"The house is beautiful and we enjoyed our stay! Just need a full length mirror in a bedroom otherwise perfect ski property!"

"My adult children and I spent Labor Day weekend working on a building project in Chester. This home was just what we needed -convenient location, 4 bedrooms set up for couples, a very serviceable kitchen (we prefer to cook for each other), solid WiFi, and a private restful outdoor space. We would definitely stay there again!"

"Roshanak was an excellent host and the place is beautiful. We love the location and its proximity to Okemo and the town. The property is gorgeous, we would book again."

Welcome to private living in Chester, VT located on 2 acres surrounded by woods

A 65" Samsung Flat Screen TV, Pool Table, Bar, Arcade & Full Bathroom!

"This property is awesome. The owners kept us well informed of what our state would be like from the booking of our trip. The view was beautiful and the house was extremely well-maintained. There was enough room for several of us to hang out and most importantly comfortably sleep. They provided us with plenty of games for the kids as well as for us adults I will definitely be booking this property again"

"The house was exactly as described and shown in the pictures. The location is PERFECT. About 10 minutes from Okemo with the cute downtown area with shops and restaurants. If it was in ski season we would be in heaven! The layout was so good for family/friends with the upstairs and downstairs bedrooms and the hosts had the home immaculate with a great eye for a cozy design and added features. The kitchen was fully stocked with everything a person would need- and a little welcome gift for the...

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Located in the Okemo Mt. Community, a mile to the base lodge

"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "

"The area was amazing and the views were incredible. "

AED 1,353 total

includes taxes & fees

26 Nov - 27 Nov

Sit by the fire and then take a dip in the pool!

"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...