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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

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 AED 621
AED 1,088 total
includes taxes & fees
27 Jan - 28 Jan
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, (64)
"The place and location are gorgeous, we absolutely loved it."
Spectacular 4 Season Home on Spruce Lake
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!"
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
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
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 AED 441
AED 1,469 total
includes taxes & fees
28 Jan - 29 Jan
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
Mount Snow Vermont - Ski - Snowboard - 6 miles
View from road

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 AED 1,010
AED 1,314 total
includes taxes & fees
26 Jan - 27 Jan
Vikings Villages Resort - Double Bed Room
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
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

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

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
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)
"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
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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.