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Compare 10 Chalets in Winchester with updated reviews, rates, and availability.

Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Outdoor dining

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (12)
"Before we arrived, James sent a list of local attractions, restaurants, hikes and other helpful establishments. He greeted us at the door right on time after coordinating via text (the app is not the most timely method). He spent some time introducing us to the house and its history. The home is beautiful and a great location for outdoor fun. He had everything you needed in the house and then some, especially in the kitchen. My only complaints (which are minor) are that the bunk bed is a little...
The price is SAR 747
SAR 1,271 total
includes taxes & fees
4 Dec - 5 Dec
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
8 minutes to Mt Snow ski & snowboard, Dog Friendly, Hot Tub, Fire Pit, Game Room
Open-concept ski chalet with modern furnishings and a wood-burning fireplace.

8 minutes to Mt Snow ski & snowboard, Dog Friendly, Hot Tub, Fire Pit, Game Room

10.0 out of 10, Exceptional, (14)
"Great place to stay! Very roomy, everything was nice and clean! We had an amazing weekend!"
8 minutes to Mt Snow ski & snowboard, Dog Friendly, Hot Tub, Fire Pit, Game Room
Mandy's Mountain Chalet minutes from Mount Snow,
Aerial view

Mandy's Mountain Chalet minutes from Mount Snow,

10.0 out of 10, Exceptional, (6)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
The price is SAR 372
SAR 1,396 total
includes taxes & fees
4 Dec - 5 Dec
Mandy's Mountain Chalet minutes from Mount Snow,
Swiss Chalet Family Retreat w/ lake access
Room

Swiss Chalet Family Retreat w/ lake access

Swiss Chalet Family Retreat w/ lake access
Vermont Green Mountains
September and October are best for viewing the changing season

Vermont Green Mountains

10.0 out of 10, Exceptional, (20)
"Easy accessible, great location , very clean and the hosts have everything to make you feel right at home , with this being said all this made for a very lovely stay "
Vermont Green Mountains
Snug Chalet - Family-Friendly, Wi-Fi + Close to Mount Snow
Living area

Snug Chalet - Family-Friendly, Wi-Fi + Close to Mount Snow

10.0 out of 10, Exceptional, (1)
"The home was very clean and our host was always available to answer questions through the app if needed. Super private spot with not a lot of traffic and there was even a nice fenced in area for the pups off the deck which was a pleasant surprise. Super close to the Inn at Quail Run which was convenient because we were attending a family reunion. Highly recommended!"
Snug Chalet - Family-Friendly, Wi-Fi + Close to Mount Snow
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
Exterior

4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi

4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
Green Mountain Chalet: Magical Summer Hideaway W/ Hot Tub Close to Mt Snow
Exterior

Green Mountain Chalet: Magical Summer Hideaway W/ Hot Tub Close to Mt Snow

Green Mountain Chalet: Magical Summer Hideaway W/ Hot Tub Close to Mt Snow
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

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

9.0 out of 10, Wonderful, (42)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Living area

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (48)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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.