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Compare 40 Vacation Homes in Winchester with updated reviews, rates, and availability.

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

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

9.8 out of 10, Exceptional, (25)
"This was the perfect spot for our family Christmas vacation. Rey spacious mansionj"
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, (132)
"This is our second Thanksgiving stay with extended family. We love it!"
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!

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!

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (16)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View

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!

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

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

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, (31)
"Will definitely book again"
Rustic Lodge with private cabins / 6 person hot tub and camp fire

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

URBAN GETAWAY - .6 Downtown Maysville/Entire House

9.2 out of 10, Wonderful, (27)
"Love this house, we have stayed here 3 times. Clean, cozy "
URBAN GETAWAY - .6 Downtown Maysville/Entire House

Beautifully renovated unit in the downtown Maysville’s entertainment district

10.0 out of 10, Exceptional, (38)
"We came to Maysville from Indiana to celebrate a friend’s birthday whose family is from the area. I found the apartment on Vrbo and it was everything we expected and then some!! Beautiful apartment, quaint neighborhood, wonderful restaurants within walking distance, and the hosts were very welcoming and responsive. I will say the stairs are every bit as steep as everyone describes, but we managed without any issues. I do caution anyone with limited abilities to consider the stairs before...
Beautifully renovated unit in the downtown Maysville’s entertainment district

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

9.4 out of 10, Exceptional, (3)
"Centrally located for us"
Luxurious & Modern newly renovated good for corporate housing & family functions

Manchester Getaway on Ohio River Scenic Byway

8.0 out of 10, Very Good, (1)
"Definitely not the best to swim but great to fish cook and hangout with the family for some peaceful time"
Manchester Getaway on Ohio River Scenic Byway

'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'

Beautifully renovated 3BR house w/lake views

10.0 out of 10, Exceptional, (24)
"Changes in Latitude was such a great find! The house has lots of room for friends and family to gather. It was clean and had everything you need for your stay. Robin was easy to communicate with and made the check in/check out process easy. "
Beautifully renovated 3BR house w/lake views

Relax and Unwind at River Front Oasis w/ Hot Tub

10.0 out of 10, Exceptional, (3)
"Awesome...."
Relax and Unwind at River Front Oasis w/ Hot Tub

Perfect Tiny Home Getaway!

6.0 out of 10, (1)
"I really never received any information really about checking in or out. Received email with code to door. Got there had no water at bathroom sink told host said probably clogged pipe never offered to come look. Messaged at 9 am about checking out n still haven’t heard back"
Perfect Tiny Home Getaway!

AFORDABLE & CHARMING HOME - Enjoy Urban Life & Nature! Hike, Bike, Shop & Dine!

10.0 out of 10, Exceptional, (1)
"Very happy with our stay! Right outside of a little downtown area and the police department is across the street. It was very quiet, which we enjoy. There are two bedrooms upstairs - queen bed and twin bed. Additionally the living room has a queen sleeper inside of the couch. Plenty of dishes, towels, and anything else you would need. Didn’t see a single bug, always a win in the middle of summer when we stay somewhere. Only two recommendations on the property are if you use the boiler setting on...
AFORDABLE & CHARMING HOME - Enjoy Urban Life & Nature! Hike, Bike, Shop & Dine!
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 !

Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (320)
"I could live there, and didn't want to leave! The cabin is cozy, laid-out and decorated beautifully. They are great hosts that show they live and take great care of the property. "
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

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

10.0 out of 10, Exceptional, (125)
"We stayed for my mom’s birthday. We took everything we needed for three nights. Very comfortable and the fire was warm in a snow storm. Lovely golden retriever came to visit as we were leaving. He was amazing. Just made our day as we are dog lovers. Thanks for letting us enjoy your place. Peaceful weekend. "
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
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.