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Compare 9 Chalets in Winchester with updated reviews, rates, and availability.

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (18)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
Beautiful Adirondack Cabin with Sauna on Lake Monomonac

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

Vikings Villages Resort - Double Bed Room

The price is AEDĀ 1,010
AEDĀ 1,347 total
includes taxes & fees
4 May - 5 May
Vikings Villages Resort - Double Bed Room

Mandy's Mountain Chalet minutes from Mount Snow,

9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
The price is AEDĀ 364
AEDĀ 1,366 total
includes taxes & fees
4 May - 5 May
Mandy's Mountain Chalet minutes from Mount Snow,

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

10.0 out of 10, Exceptional, (17)
"Great accommodations, host communicated everything very clearly, had a great weekend!"
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

Ski/Lake house for all seasons- Minutes to all

10.0 out of 10, Exceptional, (1)
"The house is amazing—perfect for a small group of friends and our kids for a ski vacation. The house has tons of space for cooking, relaxing, and playing. Several of us remarked that it was the best stocked rental we've ever stayed at. The kitchen had everything we needed to cook big meals, from cookware to tin foil. Rooms were clean, cozy and comfortable. The giant fireplace was amazing, and the hot tub was clean, hot, and perfect for relaxing after skiing. The separate game room in the...
Ski/Lake house for all seasons- Minutes to all

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

10.0 out of 10, Exceptional, (1)
"Overall we were pleased we stayed at this property, and it was a cut above many others we'd stayed at in recent years. It's very well situated for Mt Snow and great for dinner options given it's proximity to West Dover and Wilmington also with a good supermarket nearby. The space was spotless and well appointed. We struggled a little a first to find a good temperature equilibrium with 6 heating points (4 x bedrooms 2 x living levels) but we sorted it out and was not a problem after that....
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi

Mount Snow Vermont - Ski - Snowboard - 6 miles

10.0 out of 10, Exceptional, (21)
"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

Swiss Chalet Family Retreat w/ lake access

Swiss Chalet Family Retreat w/ lake access

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

10.0 out of 10, Exceptional, (2)
"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

Charming Mountain Chalet w/ Spa near Mt Snow

Charming Mountain Chalet w/ Spa near 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

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (6)
"We loved staying here! The property was sparkling clean and very well stocked with everything you need. Comfortable beds and space. The view was beautiful and the privacy and yard created great memories for our family. Thank you sharing your beautiful house with us!"
Story Book Lake Front Chateau with Private Beach!

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a large house with so many areas for activities. Close to a lot of fun things to do like axe throwing, an escape room, distilleries, breweries, etc."
GAMERS HAVEN, River Wine Inn!

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2
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.