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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, (17)
"From the moment we pulled up, when the owner met us personally late at night on the front porch, we knew this place was something special. The owner took us on a tour and explained how this land went back many generations for his family and he pointed out many nods at his past relatives - like the buck that his great grandfather and great grandmother got on a hunt many moons ago. The cabin is "Scandinavian" style and very open, with a windowed view of the water, which is barely 30 feet out the...
The price is AED 1,098
AED 1,682 total
includes taxes & fees
16 Apr - 17 Apr
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 AED 643
AED 857 total
includes taxes & fees
20 Apr - 21 Apr
Vikings Villages Resort - Double Bed Room

Mandy's Mountain Chalet minutes from Mount Snow,

9.8 out of 10, Exceptional, (9)
"The overall experience was pleasent. House was warm and bathrooms worked. The kitchen has a surprising amount of utensils. The few times I needed to reach out to the owner he responded right away. I would stay again."
The price is AED 364
AED 1,345 total
includes taxes & fees
17 Apr - 18 Apr
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 space for adults and teenagers. loved the hot tub! "
The price is AED 731
AED 2,341 total
includes taxes & fees
21 Apr - 22 Apr
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)
"The house was great. We loved the two common rooms, huge kitchen table, the beds were very comfortable, and everything was very clean and well taken care of. Not too far from Mt Snow and restaurants so worked out well!"
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

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
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.