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Search Chalets in Winchester

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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, (10)
"LIfe is a Journey - and it is worth the journey to spend time at this beautifully handcrafted, Finnish - styled home. From raising early to watch the sun rise over Lake Monomonac with coffee in hand, to a beautifully engaging conversation at dinner by the outdoor fire - you couldn't ask for more! "
The price is AED 841
AED 1,379 total
includes taxes & fees
6 Nov - 7 Nov
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
8 minutes to Mount Snow skiing, Hot Tub, Fire Pit, Game Room, Dog Friendly
Jump from the hot tub to the fire pit at your Vermont Chalet.
8 minutes to Mount Snow skiing, Hot Tub, Fire Pit, Game Room, Dog Friendly
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 Mount Snow skiing, Hot Tub, Fire Pit, Game Room, Dog Friendly
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 AED 364
AED 1,374 total
includes taxes & fees
7 Nov - 8 Nov
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
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
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

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, (41)
"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
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, (48)
"The House, Lands and View of this place are all amazing. Great for big family gathering to escape and rejoice and relax. We came to explore a bit of Vermont, which we did, but we also found ourselves reluctant to go out as the house and property were so captivating all on their own!"
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
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.