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Compare 39 Vacation Homes in Winchester with updated reviews, rates, and availability.

The Manor at Maysville Golf Course View
Exterior

The Manor at Maysville Golf Course View

9.6 out of 10, Exceptional, (15)
"This was our 2nd time staying at The Moss Manor and once again our stay was great. When we come back home to Ky if this property is available we will be staying again. Also very nice upgrades done in the house since our last stay. "
The Manor at Maysville Golf Course View
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Exterior

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

10.0 out of 10, Exceptional, (22)
"This house is a really big and beautiful home.My family and I had such a good time they suggested coming back this summer to also enjoy the outside. I did not have to wait a long time for the host to get back to me and the host Pamela was very accommodating so overall my family and I will be back this summer ."
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!
2800 sq. ft. 3-level Home, bordering Thousands of acres of Brush Creek Forest

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!
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!
Hillsboro Vacation Rental | 1,400 Sq Ft | 4BR | 3BA | Stairs Required

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
Exterior

Tranquility Cottage | 3 Bed, 1.5 Bath

9.0 out of 10, Wonderful, (10)
"Used as our family deer camp. Worked out great. "
Tranquility Cottage | 3 Bed, 1.5 Bath
'Small Town Getaway'
Exterior

'Small Town Getaway'

9.8 out of 10, Exceptional, (8)
"House was very nice and clean. Only complaint i have is not enough towels and wash rags. Many people dont reuse the wash rag after showering. I find that gross. If you dont want to add more. Get a washer/dryee so we could wash "
'Small Town Getaway'
Unique stay, hot tub, secluded
Outdoor dining

Unique stay, hot tub, secluded

7.0 out of 10, Good, (2)
"Overall I loved this spot the Grain bin itself was in a very exclusive location. There wasn’t many activities to do around the location but that didn’t bother us because we didn’t want to do a lot while we were there. The Grain Bin’s hot tub was amazing it was set at 95 degrees so if you want it hotter make sure you set it before getting in. The grill was amazing we made steaks, burger, and bacon and it was delicious!! The fire pit was great touch to our evening sunset too!!! The place was...
The price is AED 268
AED 745 total
includes taxes & fees
13 Jan - 14 January 2025
Unique stay, hot tub, secluded
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
Exterior

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
Exterior

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

10.0 out of 10, Exceptional, (59)
"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
Rustic Lodge with fireplace, WIFI, smarttv with Hulu, and massage chair.

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
LAKE HOUSE ON ROCKY FORK!
Aerial view

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (21)
"House was very clean. Lots of space. Loved having the bball court and outdoor area. "
LAKE HOUSE ON ROCKY FORK!
Beautiful Rocky Fork 2BR Cozy Cottage
Welcome to Blue Heaven Cottage

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
Peaceful Country Retreat 20 acres Private Pond
Exterior

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
Beautifully renovated unit in the downtown Maysville’s entertainment district
Room

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
Exterior

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
Manchester Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required

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
Carriage House Farm-stay near Rocky Fork Lake
Enjoy 1900 square feet of peaceul living space here on the farm.

Carriage House Farm-stay near Rocky Fork Lake

10.0 out of 10, Exceptional, (17)
"The location of this property is beautiful and serene. The interactions I had with the hosts were very positive and left a great impression on me. The house had everything we needed and more for a comfortable stay, and it was clear the hosts went the extra mile. It was amazing to take a walk and see their livestock and play with their friendly dogs. I’m very thankful for the time I spent there."
Carriage House Farm-stay near Rocky Fork Lake
Beautifully renovated 3BR house w/lake views
Front of house with fun directional sign

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
Interior

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!
Private kitchen

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!
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 !
Deerpath Cabin

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

10.0 out of 10, Exceptional, (254)
"Our stay at this cabin was great! It had everything we needed and more. The location was very peaceful. We saw deer in the backyard. The cabin was beautiful. I highly recommend staying here! The only thing it needs is curtains in the bedrooms. Otherwise everything was fantastic and we would stay here again! Thanks so much! "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
Terrace/patio

Amish-built cabin, serene and peaceful with pond and private dock for fishing.

10.0 out of 10, Exceptional, (16)
"Enjoyed some nice relaxing mid-week downtime! Crazy weather, started with 60's and beautiful sunsets and ended this morning with snow and biting cold!"
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Exterior

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

10.0 out of 10, Exceptional, (22)
"This house is a really big and beautiful home.My family and I had such a good time they suggested coming back this summer to also enjoy the outside. I did not have to wait a long time for the host to get back to me and the host Pamela was very accommodating so overall my family and I will be back this summer ."
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
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.