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Compare 46 Vacation Homes in Winchester with updated reviews, rates, and availability.

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
9.8 out of 10, Exceptional, (28)

Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound
Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound
9.8 out of 10, Exceptional, (136)

A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More
A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (22)

LAKE HOUSE ON ROCKY FORK!
LAKE HOUSE ON ROCKY FORK!
9.4 out of 10, Exceptional, (24)

Peaceful Country Retreat 20 acres Private Pond
Peaceful Country Retreat 20 acres Private Pond
9.8 out of 10, Exceptional, (20)

'Small Town Getaway'
'Small Town Getaway'
9.8 out of 10, Exceptional, (11)

Tranquility Cottage | 3 Bed, 1.5 Bath
Tranquility Cottage | 3 Bed, 1.5 Bath
9.0 out of 10, Wonderful, (11)
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

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (259)

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (129)

Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound
Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound
9.8 out of 10, Exceptional, (136)
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

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
5/5 Excellent
Excellent experience!
"Beautiful home! Beautiful country! The house was clean, inviting, and had everything we needed! "
A verified traveler stayed at Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Posted 10 days ago