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Compare 109 Vacation Homes in Winchester with updated reviews, rates, and availability.
Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
9.8 out of 10, Exceptional, (17)
The price is AED 474
AED 792 total
includes taxes & fees
18 Feb - 19 Feb
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (51)
Cozy cottage tucked away in the woods
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, (40)
Charming Waterfront Log Cabin
Charming Waterfront Log Cabin
9.6 out of 10, Exceptional, (37)
Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths
Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths
Hilltop Home with Great Views
Hilltop Home with Great Views
9.2 out of 10, Wonderful, (12)
River House
River House
10.0 out of 10, Exceptional, (7)
The Dover Hideaway | Hot Tub & Close to Mt. Snow
The Dover Hideaway | 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
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
9.8 out of 10, Exceptional, (113)
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (51)
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
10.0 out of 10, Exceptional, (14)
The price is AED 621
AED 1,080 total
includes taxes & fees
12 Feb - 13 Feb
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
5/5 Excellent
"Nice oka e always our go-to for volleyball tournament as it is not far from Game On athletic center "
A verified traveler stayed at The Colonial Hotel
Posted 2 days ago