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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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, (14)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
The price is SAR 634
SAR 1,111 total
includes taxes & fees
4 Feb - 5 Feb
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
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, (65)
"The place and location are gorgeous, we absolutely loved it."
Spectacular 4 Season Home on Spruce Lake
Mandy's Mountain Chalet minutes from Mount Snow,
Aerial view

Mandy's Mountain Chalet minutes from Mount Snow,

10.0 out of 10, Exceptional, (7)
"We had a very nice stay at Mandy’s Mountain Chalet. We had a nice lazy Christmas with TV and a lot of nice food :) maybe the pellet fireplace is not the coziest option, but it was definitely practical. "
The price is SAR 544
SAR 1,623 total
includes taxes & fees
11 Feb - 12 Feb
Mandy's Mountain Chalet minutes from Mount Snow,
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
Mount Snow Vermont - Ski - Snowboard - 6 miles
Living area

Mount Snow Vermont - Ski - Snowboard - 6 miles

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 - 6 miles
Vikings Villages Resort - Double Bed Room
Exterior

Vikings Villages Resort - Double Bed Room

The price is SAR 1,031
SAR 1,342 total
includes taxes & fees
4 Feb - 5 Feb
Vikings Villages Resort - Double Bed Room
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

10.0 out of 10, Exceptional, (1)
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Open-concept ski chalet with modern furnishings and a wood-burning fireplace.

8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, 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 1,159
SAR 2,950 total
includes taxes & fees
13 Feb - 14 Feb
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
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
Swiss Chalet Family Retreat w/ lake access
Room

Swiss Chalet Family Retreat w/ lake access

Swiss Chalet Family Retreat w/ lake access
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

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (112)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.8 out of 10, (13)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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.