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9 Jum. I - 11 Jum. I

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16 Jum. I - 18 Jum. I

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

"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"

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

SAR 2,193 total

includes taxes & fees

5 May - 6 May

"Beautiful place."

"House was great. We were able to walk up the road with our skis and drop right in. I’d definitely stay here again."

"This was our second Thanksgiving at Creekside Camp. Once again, we had a wonderful stay. Not enough can be said about this charming and cozy cabin. Dan and Kellie do a phenomenal job as hosts and managing the property. We highly recommend a stay in this rustic, yet highly appointed property!"

"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!"

"This place was great for my family and I. It is very close to Okemo and town "

"Beautiful cozy cottage, but the road is a little loud. The creek and backyard are gorgeous."

"We had an absolute amazing stay at Todd‘s place. Communication was extremely responsive. This was a last-minute trip with the family during the holiday and we had an absolute blast. The kids had so much fun in the bunk bedroom. The house is extremely spacious and absolutely beautiful. To be able to ski to the backyard was such a luxury. This was a special house with an unreal location. We will be coming back in February. Thank you so much for the memories."

"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice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 for our family of 7. Plenty of room in the house to spread out. Enjoyed the fireplace - plenty of wood provided."

"The barn is beautiful and much more spacious than it looks in the photos. The property the barn is on is also beautiful, a short drive from the town center, and also close to cool sites to visit like the Lincoln House and many amazing hiking trains."

"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 1,277 total

includes taxes & fees

5 May - 6 May

"Great location for ski in/out. Ideal for a small family "

"Quiet and private location on a spectacular piece of protected land."

"Close to skiing"

"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!"

"Lovely rustic and cozy cabin stay"

"This rental was stunning! Such a cool property with so many different spaces for a large group to spend time. Everything was labeled for ease of access (very grateful for this!), we enjoyed many of the amenities, and communication with the host was fast! Wonderful stay with no issues!H"

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"Peaceful vacation"

"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "

SAR 2,415 total

includes taxes & fees

5 May - 6 May