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Featured Chalets in Chester and around

Our top choices for Chester chalets

"When we first arrived we couldn’t find extra trash bags. We sent a message to the host, Jason, and he replied immediately to assist us. I appreciate the attentiveness and genuine hospitality. This place is cozy and clean. Made for the perfect weekend getaway!"

includes taxes & fees

24 Aug - 25 Aug

"Really enjoyed this home. Was a weekend getaway with friends and there was lots of room for us. Especially enjoyed the sauna. Kitchen is well stocked. All was great. "

"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."

includes taxes & fees

25 Aug - 26 Aug

"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."

"Girls family weekend, relaxing, visiting and enjoying the hot tub."

"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "

"All around great stay. Had some slight heat issues day 1 that were fixed imemdiately!"

"We had an amazing trip, and the host was very responsive and helpful with everything. The house was great, had everything we needed, and the private ski run back to the property was really fun. Highly recommend this property and the best host we have ever had!! Favoriting this place for a future stay!"

includes taxes & fees

1 Sept - 2 Sept

"House was great, we loved our stay. Definitely walk down the road and get pizza! It was our favorite dinner of our trip and absolutely delicious! "

"We had a great time at the Wine Moose! The sauna kept us super warm in the super cold temps. Very very close to Mt. Snow and we also hit up Berkshire East and Magic an hour south and north respectively, easily. I'd recommend staying here!"

"This spot was perfect for a weekend at mount snow! It was so quick to get to the mountain and good area for food and shops. I would definitely stay here again!"

includes taxes & fees

26 Aug - 27 Aug

"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."

includes taxes & fees

1 Sept - 2 Sept

"We spent the week, excellent location and the home was exactly as described in listing."

includes taxes & fees

21 Aug - 22 Aug

"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "

"A terrific place. Highly recommended. We had a great family ski vacation."

"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "

"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "

includes taxes & fees

21 Aug - 22 Aug

"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"