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

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."

"Nice location. Plenty of room for 6 adults. Pellet stove and Christmas movies after a day of shopping and exploring made for a perfect night. "

AED 2,505 total

includes taxes & fees

8 Jan - 9 January 2025

"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....

"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"

AED 1,765 total

includes taxes & fees

30 Dec - 31 Dec

"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."

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

"Stay was perfect"

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

"My family and close friends got together for the second year here. We enjoyed it so much last year we extended our stay this year. We had the same magnificent experience this year. We enjoy making family style meals in the big open kitchen. Plenty of space for all of us to lounge around. We always make sure to use the hot tub while we're there. They did some nice updates since we were there last year. The new shower head in the downstairs bathroom is great! We'll be making this an annual family...

"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."

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

"A relaxing weekend with family. Perfect place for two couples or a small family. Close to mountains, restaurants and shopping. We over packed bringing more pans and cooking equipment since many rentals are not as equipped. Owner communicated well. Had a much needed and relaxing long weekend. It snowed and the driveway and roads were cleared nicely, so we were able to travel when and where we wanted."

"We enjoyed our stay during the holiday week. The fenced in yard for our pups was definitely a plus and hard to find in a rental. Just a note of caution regarding the stairs in the home. They are very steep, and we had an elderly family member with us. Luckily there is a first-floor bedroom and bathroom, so all worked out fine. The owners were very responsive to any questions we had. Is a lovely spot and would recommend it to others. "

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!"

"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!"

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

"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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Other property types in Charlestown

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 tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."

AED 1,804 total

includes taxes & fees

1 Jan - 2 January 2025

"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...