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Compare 85 Chalets in Chester 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. "

SAR 2,735 total

includes taxes & fees

27 Dec - 28 Dec

"Close to EVERYTHNIG!"

"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....

Look at that amazing sky! I didn't know which direction to capture in this photo. Wait till you see in the other direction. Beautiful mountain views. This spot is stunning. Get a fire going in the fire pit and you're set.

"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"

"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...

"The house was very cozy and easy to get comfortable. It is surrounded by woods. We were lucky to get a lot of snow one day of our stay so we were literally in a magnificent winter wonderland-a perfect stay!"

"House is great, we had a large group. 2 living rooms, one with tv one without was a nice separation. To give some details on the layout, the bunk bed rm and twin room are off the living room on the main level, all other bd rooms are on the second floor. From the parking area to the main front door there are 31 steps.... not sure that was stated anywhere but hopefully everyone reads this review. I will stay here again if my group size demands it, it's close to mt snow, pretty secluded overall...

"This property is absolutely perfect for a large group staying at Stratton. Plenty of bedrooms / beds / baths, open space around the kitchen and living room areas, plenty of parking and more. Fireplace is great. Hot tub and sauna come in clutch. Location is ideal. Owner communicates great. We were a group of 9 friends up for a quick ski trip. Would definitely book it again."

"Not as described "

"Overall, a very good stay. The house is a bit smaller than we thought, but it was very clean and well stocked. The indoor fireplace and provided wood was a nice perk. The hot tub was not clean or well kept, so beware of that. There were body hairs and a brown scum ring around the edge."

"This property was gorgeous and well maintained, and the hosts were very responsive and helpful. The beautiful open upstairs area was the perfect balance of modernized rustic charm with all the necessary amenities & a nice deck with a hot tub - and the game room downstairs had air hockey, pac man, and Nintendo 64 to keep us entertained during the rainy periods of our stay. Despite the property itself being nice and private and rural, the chalet was actually more conveniently located than I had...

SAR 3,073 total

includes taxes & fees

5 Jan - 6 January 2025

SAR 1,805 total

includes taxes & fees

24 Dec - 25 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."

Updated ski chalet, in the mountains of southern Vermont, 1 minute from Mt Snow

SAR 4,181 total

includes taxes & fees

8 Jan - 9 January 2025

"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."

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

"Stay was perfect"

"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."

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Other property types in Chester

"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "

SAR 1,770 total

includes taxes & fees

6 Jan - 7 January 2025

"Like property— sad the lift that made it ski and in out was closed due weather conditions "

SAR 2,479 total

includes taxes & fees

26 Dec - 27 Dec

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 "