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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Exterior

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (16)
"It was my second time staying at the Finnish House and I am already planning another trip. Jim is a fantastic host and the property is immaculate!"
The price is AED 1,098
AED 1,682 total
includes taxes & fees
27 Mar - 28 Mar
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Spectacular 4 Season Home on Spruce Lake
Exterior

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
Interior

Vikings Villages Resort - Double Bed Room

The price is AED 1,010
AED 1,347 total
includes taxes & fees
27 Mar - 28 Mar
Vikings Villages Resort - Double Bed Room
Mandy's Mountain Chalet minutes from Mount Snow,
Exterior

Mandy's Mountain Chalet minutes from Mount Snow,

10.0 out of 10, Exceptional, (8)
"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
27 Mar - 28 Mar
Mandy's Mountain Chalet minutes from Mount Snow,
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Outdoor spa tub

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 621
AED 2,191 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
4 bedrooms, desk, iron/ironing board, WiFi

Ski/Lake house for all seasons- Minutes to all

Ski/Lake house for all seasons- Minutes to all
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
Dining

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
Exterior

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
2 bedrooms, iron/ironing board, travel crib, free WiFi

Swiss Chalet Family Retreat w/ lake access

Swiss Chalet Family Retreat w/ lake access
Snug Chalet - Family-Friendly, Wi-Fi + Close to Mount Snow
Exterior

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
Green Mountain Chalet: Magical Summer Hideaway W/ Hot Tub Close to Mt Snow
Outdoor spa tub

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

Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,102
AED 1,909 total
includes taxes & fees
3 Apr - 4 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"The Jelly Mill is a lovely, welcoming cottage in the S. VT town of Guilford, nestled in the hills below the bigger town of Brattleboro. The location feels 'out of the way' - no big roads (or even paved roads), stores, 'hustle or bustle' anywhere close by - but Brattleboro has all that stuff and is only 20-30 minutes away. For 'last minute' items a charming, smaller grocery / sandwich shop is closer by. The property itself is very clean, with an up to date kitchen and glitch-free speedy Wi-Fi...
The Jelly Mill-A River Retreat
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (16)
"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.