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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, (26)
"We had a large family reunion and we were all very comfortable from little kids to adults. Everything we could’ve possibly wanted …it was there. We had a very minor situation and it was corrected within 20 minutes. We would definitely return. Wonderful memories were made! Thank you for being a part of that!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!

9.8 out of 10, Exceptional, (135)
"Set on the edge of a State Forest, it is secluded and comfortable. The owners were great with communication and even left me a Birthday Card for my 70th. Nice touch. Thank you si much "
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!

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, (23)
"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'

9.6 out of 10, Exceptional, (10)
"got to the house and was very cold, blankets weren't very heavy, place was clean, location was'nt very good. "
'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)
"Our family of 20 including 12 kids ages 1-12 was fun. The outside of the house looks small, but we had plenty of room inside. The only downside for a cold weather visit with kids is there is only one bathroom in the house. Other restrooms are in the adjacent shower house. So the short walk to the bathroom was a bit chilly. "
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)
"Booked this place for a board game retreat and will be back! Great communication before and during with the hosts. Huge kitchen, very well-maintained hot tub, and massage chair! PRO: it's one large room!CON: it's one large room!If your group has both early risers AND late risers, I would recommend separating them so one group has the separate small cabins and the other group takes the beds above the lodge.5 actual beds, the rest are (very comfy) pull-out couches. No one in our group sharing the...
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)
"My family and friends had a fantastic stay at the Manor! The space offers plenty of room, making it perfect for relaxing or getting work done. The Wi-Fi was excellent, which was a huge plus. The host was incredibly responsive, ensuring a smooth and hassle-free experience. Plus, the location is awesome—close to everything you need. Highly recommend!"
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!

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

Unique stay, hot tub, secluded

8.6 out of 10, Excellent, (4)
"Quiet, secluded, clean, plenty of room for a couple and ample kitchen space and equipment to cook meals... We did our annual couples retreat at Harvest Haven and really got the headspace for goalsetting and reviewing the past year. The rose petals on the bed were a nice touch. The skies were clear and we were able to see so many stars at night. The hottub was perfect. We visited Amish shops, a local diner, and Serpent Mound, but spent most of our time at the silo. It was wonderful to get away...
The price is SAR 413
SAR 956 total
includes taxes & fees
7 Apr - 8 Apr
Unique stay, hot tub, secluded

Beautiful Rocky Fork 2BR Cozy Cottage

10.0 out of 10, Exceptional, (106)
"We enjoyed our stay at Robin's cottage. Everything was clean and comfortable. Great communication. The kitchen had everything we needed. We really appreciated the fire pit and firewood. Self check-in was easy. Thank you for hosting us. "
Beautiful Rocky Fork 2BR Cozy Cottage

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

~Lakeside Escape ~ Waterfront w/Hot Tub

~Lakeside Escape ~ Waterfront w/Hot Tub

Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!

8.8 out of 10, Excellent, (5)
"The house was very clean and cozy inside with many great features. Outside there were bees swarming around the front corner of the hot tub. The gas tank on the grill was empty and there were many bugs accumulated on the outside of the house near the doors that needed cleaned. . "
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!

Beautifully renovated unit in the downtown Maysville’s entertainment district

10.0 out of 10, Exceptional, (39)
"What a beautiful property. It was an absolute pleasure to stay there. The host was easy to communicate with and super concerned that our stay was the best.It was. I will look to stay here in future trips to Maysville"
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, (257)
"The cabin was wonderful and the host was great! We got about 14 inches of snow while there and the views were absolutely gorgeous. Had a few hiccups but the host was right there when we needed him. He was extremely friendly and helpful. Will definitely stay again!"
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, (127)
"The cabin is modern, cozy and clean and comes with everything you need!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

The Cabin at 114 Main Street

9.6 out of 10, Exceptional, (34)
"Great location, extremely clean, clear directions, and cute outside area too. It was a terrific birthday weekend. We will definitely be back. "
The price is SAR 521
SAR 878 total
includes taxes & fees
1 Apr - 2 Apr
The Cabin at 114 Main Street
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.