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Compare 1086 Vacation Homes in Chester with updated reviews, rates, and availability.

"Very nice. Could use curtains or blinds in more rooms."

"Online info was accurate. Nice spot to rent with family."

SAR 1,950 total

includes taxes & fees

3 Apr - 4 Apr

"House is 1 minute or less from the Skye Peak Gondola, which as convenient for skiing. Clean house, has lots of room and games for families. Hot tub was really nice too."

"Our group had a great time enjoying this bright open space. Such a pretty place. Michael was very responsive and communications were timely and simple. Nice place for gathering."

"Long weekend with friends and our beloved old dog. We were anxious to get back to Vermont and this home was just what we needed. Close to the activities we like, cross country skiing, great book store, cute shops. Accommodations were above what we expected. Dan could not be a better host. We will be back!"

"Stayed at this lovely home for a short weekend trip in the winter. Very convenient location, clean and well kept. Be sure to have AWD and proper tires if you visit in the winter!"

"Had a business retreat with 6 associates. The cabin was great and operated as one would expect for a ski cabin. Nice fire place and hot tub. The TVs are older so they have a hard time connecting to the WIFI for Netflix, Prime, etc. I recommend bringing agame console aor "

"If your looking for beauty nature and comfort this cozy cottage surpassed our expectations our dog loved the lake and ducks and snow we lived ludlow okemo woodstock and Westin all so close great location and our host was wonderful prompt response with any questions and added a night last minute for us thanks so much Kristin "

"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "

"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"

"Great house. Great location. Clean and well stocked house "

"Great secluded place. Very clean couldn't ask for more. Great central location. Close to restaurants "

"We were caught in the winter storm, and the host was so kind in helping us navigate our car situation. Our kids had such a great time playing in the snow, exploring the books and games they had. "

SAR 1,281 total

includes taxes & fees

30 Mar - 31 Mar

"Fantastic location for easy ski on ski off."

"The house was beautiful inside and out. Everything was very clean and very comfortable, and the view of the lake was outstanding. For the winter months the lower level with the pool table was cold, but we were still able to enjoy it. The host of the property had exceptionally good communication and was attentive and helpful. We were very happy with our stay and would definitely go back again. "

"Fantastic Vermont farm house in a great setting close to Okemo and Killington. Very accommodating, clean, warm and comfortable. After skiing we enjoyed just sitting around the fireplace and talking. We plan on returning next year."

"Great value and location to Okemo. Place was comfortable and clean and to our surprise there was a refrigerator that wasn’t noted in the listing that came in very handy. Would stay again."

"We were VERY pleasantly surprised to see a Christmas tree and a fully decorated house! The kids absolutely loved it. That said, the house in general was child friendly in every way - dinnerware and utensils, toys, appropriate sleeping options, and others. It was perfect for meeting familu from all over!"

"We were absolutely delighted with our stay at the villa. The house is big, spacious, and most importantly, clean. The house has everything you need for a comfortable stay. Everything is thought out to the smallest detail. We had both kids and teenagers with us - everyone felt comfortable. Lots of space, a large table for a large company. The location is literally 3 minutes from the city center, where there are many shops and restaurants. 30 minutes from the ski resort. There were no problems...

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Other property types in Chester

"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"