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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

9.8 out of 10, Exceptional, (28)
"Host is helpful and check in/out was a breeze!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound

9.8 out of 10, Exceptional, (136)
"We had a great time. The house was cozy and secluded. "
Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound

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

10.0 out of 10, Exceptional, (22)
"The place was huge, clean, and amazing! Would recommend to anyone! "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (24)
"Perfect spot for my family to get together for Christmas! Easy to get to, cozy and nice backyard cause I have dogs. Just a great place to stay!"
LAKE HOUSE ON ROCKY FORK!

Peaceful Country Retreat 20 acres Private Pond

9.8 out of 10, Exceptional, (20)
"Great place to stay! Very serene. It was tough to get a comfortable temperature in all areas of the home at the same time & the water pressure isn’t great, but otherwise we had a very nice stay there. "
Peaceful Country Retreat 20 acres Private Pond

'Small Town Getaway'

9.8 out of 10, Exceptional, (11)
"Host responsive and place was clean "
'Small Town Getaway'

Tranquility Cottage | 3 Bed, 1.5 Bath

9.0 out of 10, Wonderful, (11)
"I have stayed here before 2 years ago. Great location if hunting in Peebles. Other than the heating system being a bit clunky (noisy at night) when running. It’s a really well kept place. "
Tranquility Cottage | 3 Bed, 1.5 Bath

Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats

10.0 out of 10, Exceptional, (60)
"Good space for family gatherings!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats

Rustic Lodge with private cabins / 6 person hot tub and camp fire

10.0 out of 10, Exceptional, (32)
"Will definitely book again"
Rustic Lodge with private cabins / 6 person hot tub and camp fire

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (17)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View

~Lakeside Oasis~ Waterfront w/HotTub, Sauna & Dock

10.0 out of 10, Exceptional, (2)
"A group of us stayed for a hiking weekend, and we absolutely loved the place. It was one I’ve the best rentals I’ve stayed at. "
~Lakeside Oasis~ Waterfront w/HotTub, Sauna & Dock

Luxurious & Modern newly renovated good for corporate housing & family functions

9.6 out of 10, Exceptional, (4)
"it was great"
Luxurious & Modern newly renovated good for corporate housing & family functions

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

8.0 out of 10, Very Good, (1)
"It was good. Thank you "
The price is SAR 597
SAR 836 total
includes taxes & fees
5 May - 6 May
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

Unique stay, hot tub, secluded

8.6 out of 10, Excellent, (4)
"Perfect spot. Has everything you need. Such a cool dwelling design and decor. You have to see it for yourself! "
The price is SAR 456
SAR 949 total
includes taxes & fees
28 Apr - 29 Apr
Unique stay, hot tub, secluded

Beautiful Rocky Fork 2BR Cozy Cottage

10.0 out of 10, Exceptional, (106)
"We really enjoyed our stay in this cute little cottage. Great location and Robin was very helpful during our stay. Would definitely recommend and stay here again!"
Beautiful Rocky Fork 2BR Cozy Cottage

~Lakeside Escape ~ Waterfront w/Hot Tub (NEW FEATURES!)

~Lakeside Escape ~ Waterfront w/Hot Tub (NEW FEATURES!)

House with private boat dock and beautiful scenic view on the Ohio River

10.0 out of 10, Exceptional, (1)
"My boyfriend and I wanted a nice, private, relaxing weekend away and this place was exactly what we were looking for. The property is large enough that it is private, no one on either side. We enjoyed the large covered deck with 2 ceiling fans, comfortable furniture, and a nice fire table we really enjoyed in the evenings. There is a second deck where I enjoyed drinking my coffee in the morning and soaking up the sun in the afternoons. You can sit and watch all the boaters go by and it has a...
House with private boat dock and beautiful scenic view on the Ohio River

Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!

8.8 out of 10, Excellent, (5)
"It was the perfect space near family to introduce them to the newest member all the way from Louisiana - 4 generations. Having 3 queen bedrooms and a big couch to hangout on was perfect"
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!

Beautifully renovated unit in the downtown Maysville’s entertainment district

10.0 out of 10, Exceptional, (40)
"Very nice place. It was as pictured and contained everything we needed. The view of the river from the deck was beautiful. "
Beautifully renovated unit in the downtown Maysville’s entertainment district
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 !

10.0 out of 10, Exceptional, (259)
"I’m perfect for a small group to have a relaxing getaway "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

10.0 out of 10, Exceptional, (129)
"It was just as nice in person as it looked on line. It was very relaxing and everything we needed was all there. We will definitely be returning there again. A. "
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound

9.8 out of 10, Exceptional, (136)
"We had a great time. The house was cozy and secluded. "
Paradise Bordering Forest! Large Private Home-Free Parking Pass to Serpent Mound
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.