Photo by Donny Campos
Search Chalets in Winchester
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 9 Chalets in Winchester with updated reviews, rates, and availability.

Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
10.0 out of 10, Exceptional, (18)

Spectacular 4 Season Home on Spruce Lake
Spectacular 4 Season Home on Spruce Lake
9.8 out of 10, Exceptional, (65)

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

Mandy's Mountain Chalet minutes from Mount Snow,
Mandy's Mountain Chalet minutes from Mount Snow,
9.8 out of 10, Exceptional, (9)
The price is AEDĀ 364
AEDĀ 1,366 total
includes taxes & fees
4 May - 5 May

8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
10.0 out of 10, Exceptional, (17)

Ski/Lake house for all seasons- Minutes to all
Ski/Lake house for all seasons- Minutes to all
10.0 out of 10, Exceptional, (1)

4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
10.0 out of 10, Exceptional, (1)

Mount Snow Vermont - Ski - Snowboard - 6 miles
Mount Snow Vermont - Ski - Snowboard - 6 miles
10.0 out of 10, Exceptional, (21)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Winchester

Story Book Lake Front Chateau with Private Beach!
Story Book Lake Front Chateau with Private Beach!
10.0 out of 10, Exceptional, (6)

GAMERS HAVEN, River Wine Inn!
GAMERS HAVEN, River Wine Inn!
10.0 out of 10, Exceptional, (11)

Riverfront 2 Bedroom Unit 2
Riverfront 2 Bedroom Unit 2
9.6 out of 10, Exceptional, (17)
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.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels

Hampton Inn & Suites Keene
5/5 Excellent
"They had good options for Breakfast. Everything was clean. I enjoyed my stay. "
A verified traveler stayed at Hampton Inn & Suites Keene
Posted 2 days ago