Photo by Donny Campos
Search Chalets in Winchester
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Chalets in Winchester
Compare 11 Chalets in Winchester with updated reviews, rates, and availability.
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
10.0 out of 10, Exceptional, (13)
The price is AED 694
AED 1,184 total
includes taxes & fees
6 Jan - 7 January 2025
8 minutes to Mt Snow ski & snowboard, Dog Friendly, Hot Tub, Fire Pit, Game Room
8 minutes to Mt Snow ski & snowboard, Dog Friendly, Hot Tub, Fire Pit, Game Room
10.0 out of 10, Exceptional, (14)
The price is AED 1,245
AED 3,233 total
includes taxes & fees
20 Jan - 21 January 2025
Mandy's Mountain Chalet minutes from Mount Snow,
Mandy's Mountain Chalet minutes from Mount Snow,
10.0 out of 10, Exceptional, (6)
The price is AED 441
AED 1,465 total
includes taxes & fees
7 Jan - 8 January 2025
Swiss Chalet Family Retreat w/ lake access
Swiss Chalet Family Retreat w/ lake access
Spectacular 4 Season Home on Spruce Lake
Spectacular 4 Season Home on Spruce Lake
9.8 out of 10, Exceptional, (64)
Mount Snow Vermont - Ski - Snowboard - 10 mins
Mount Snow Vermont - Ski - Snowboard - 10 mins
10.0 out of 10, Exceptional, (20)
Viking Village Resort
Viking Village Resort
The price is AED 1,286
AED 1,637 total
includes taxes & fees
25 Dec - 26 Dec
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)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Winchester
Charming Waterfront Log Cabin
Charming Waterfront Log Cabin
9.6 out of 10, Exceptional, (37)
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)
Hilltop Home with Great Views
Hilltop Home with Great Views
9.2 out of 10, Wonderful, (12)
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
5/5 Excellent
"We love staying at the latchis. They always go above and beyond with customer service. And the place is spotlessly clean. "
A verified traveler stayed at Latchis Hotel
Posted 2 days ago