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Compare 11 Chalets in Winchester with updated reviews, rates, and availability.

8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
10.0 out of 10, Exceptional, (17)
The price is SAR 1,309
SAR 3,145 total
includes taxes & fees
13 Mar - 14 Mar

Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
10.0 out of 10, Exceptional, (16)
The price is SAR 634
SAR 1,131 total
includes taxes & fees
12 Mar - 13 Mar

Mandy's Mountain Chalet minutes from Mount Snow,
Mandy's Mountain Chalet minutes from Mount Snow,
10.0 out of 10, Exceptional, (8)
The price is SAR 450
SAR 1,483 total
includes taxes & fees
24 Mar - 25 Mar

Vikings Villages Resort - Double Bed Room
Vikings Villages Resort - Double Bed Room
The price is SAR 1,031
SAR 1,367 total
includes taxes & fees
9 Mar - 10 Mar

4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
10.0 out of 10, Exceptional, (1)

Mount Snow Vermont - Ski - Snowboard - 6 miles
Mount Snow Vermont - Ski - Snowboard - 6 miles
10.0 out of 10, Exceptional, (21)

Snug Chalet - Family-Friendly, Wi-Fi + Close to Mount Snow
Snug Chalet - Family-Friendly, Wi-Fi + Close to Mount Snow
10.0 out of 10, Exceptional, (1)

Swiss Chalet Family Retreat w/ lake access
Swiss Chalet Family Retreat w/ lake access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winchester

Secluded Lakefront Vacation Home
Secluded Lakefront Vacation Home
9.8 out of 10, Exceptional, (69)

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
8.8 out of 10, Excellent, (46)

Cozy 2-bedroom Unit with private backyard
Cozy 2-bedroom Unit with private backyard
10.0 out of 10, Exceptional, (21)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels

The Putney Inn
5/5 Excellent
" Great property, great staff and management, affordable and clean!"
A verified traveler stayed at The Putney Inn
Posted 2 days ago