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Compare 11 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, (13)
"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 710
SAR 1,202 total
includes taxes & fees
7 Jan - 8 Jan
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
8 minutes to ski Mount Snow, Dog Friendly, Hot Tub, Fire Pit, Game Room, Private
Open-concept ski chalet with modern furnishings and a wood-burning fireplace.

8 minutes to ski Mount Snow, Dog Friendly, Hot Tub, Fire Pit, Game Room, Private

10.0 out of 10, Exceptional, (15)
"Great place to stay! Very roomy, everything was nice and clean! We had an amazing weekend!"
The price is SAR 1,311
SAR 3,354 total
includes taxes & fees
20 Jan - 21 Jan
8 minutes to ski Mount Snow, Dog Friendly, Hot Tub, Fire Pit, Game Room, Private
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 432
SAR 1,465 total
includes taxes & fees
6 Jan - 7 Jan
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
Spectacular 4 Season Home on Spruce Lake
Lake house with private beach area

Spectacular 4 Season Home on Spruce Lake

9.8 out of 10, Exceptional, (64)
"The place and location are gorgeous, we absolutely loved it."
Spectacular 4 Season Home on Spruce Lake
Mount Snow Vermont - Ski - Snowboard - 10 mins
Upstairs sitting area

Mount Snow Vermont - Ski - Snowboard - 10 mins

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 "
Mount Snow Vermont - Ski - Snowboard - 10 mins
Viking Village Resort
Exterior

Viking Village Resort

The price is SAR 1,315
SAR 1,666 total
includes taxes & fees
2 Jan - 3 Jan
Viking Village Resort
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
Ski/Lake house for all seasons- Minutes to all
Entry to Dining and Kitchen. Ladder to the Loft

Ski/Lake house for all seasons- Minutes to all

Ski/Lake house for all seasons- Minutes to all
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

Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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, (43)
"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
Hilltop Home with Great Views
Exterior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
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.