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Compare 35 Vacation Homes in Winchester with updated reviews, rates, and availability.

URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.4 out of 10, Exceptional, (25)
"Very comfortable. Accessible location to places we wanted to visit. "
The price is AED 290
AED 446 total
includes taxes & fees
20 Nov - 21 Nov
URBAN GETAWAY - .6 Downtown Maysville/Entire House
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!
9.8 out of 10, Exceptional, (130)
"Beautiful, peaceful and private. Overall we had a great time. We were a bit disappointed by the Wi-Fi rules as they were not specified in the listing and the extensive DVD collection turned out to be less than 20 and most were from the 60’s and 70’s. Other than that we had a great time. Lots of fires and s’mores and reconnecting with family."
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!
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
10.0 out of 10, Exceptional, (104)
"Comfortable beds, excellent towels. God kitchen set up/."
Beautiful Rocky Fork 2BR Cozy Cottage
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (21)
"Really large house that accommodated our group in town for my Son’s wedding. Lower level appears to have been a former business as 3 of the rooms were offices. Only other issue was a lack of a shower/tub in the lower level."
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
10.0 out of 10, Exceptional, (57)
"Looking forward to booking again for next summer. Perfect property and plenty of space!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Peaceful Country Retreat 20 acres Private Pond
9.8 out of 10, Exceptional, (19)
"This is a really nice big house. Plenty of room for many adults. This place had everything we needed for a weeks stay consisting of 7 grown men. I plan to book another week next year. "
Peaceful Country Retreat 20 acres Private Pond
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 price is AED 1,286
AED 2,547 total
includes taxes & fees
17 Nov - 18 Nov
The Manor at Maysville Golf Course View
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 294
AED 796 total
includes taxes & fees
9 Dec - 10 Dec
Unique stay, hot tub, secluded
Rustic Lodge with private cabins / 6 person hot tub and camp fire
10.0 out of 10, Exceptional, (30)
"Lovely place with lots of room! Had tons of fun in the hot tub and the fire pit! 1000000% recommend for a fun friends outing! "
Rustic Lodge with private cabins / 6 person hot tub and camp fire
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 3BR house w/lake views
10.0 out of 10, Exceptional, (23)
"House was absolutely beautiful, with everything you need for a comfortable stay. Stocked with little extras that you may have forgotten to pack. Our family is already planning our next trip back to Rocky Fork. Robin was great with communication and everything was perfect for our stay! "
Beautifully renovated 3BR house w/lake views
Jewel Box Cottage in Historic Maysville KY
9.2 out of 10, Wonderful, (7)
"The house was wonderful place for family to gather after funeral of my father. My mother wanted us to be able to gather together for stories, laughter & tears. This gave us privacy to do so. Booking & checking in was very easy. We found it very clean except for some "sticky" kitchen cabinet doors/drawers. The only "issue" we had was not finding outlets in the bedrooms......after a good night's rest we realized the next morning that they were located in the baseboards of the same color! Will...
The price is AED 826
AED 1,386 total
includes taxes & fees
17 Nov - 18 Nov
Jewel Box Cottage in Historic Maysville KY
River House with AC and WiFi in welcoming Ripley, Ohio
2.0 star property
River House with AC and WiFi in welcoming Ripley, Ohio
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (19)
"This house was perfect for us, family meeting for my terminally ill mother. It was perfect, plenty of room, everyone had their own room to rest, lots to do outside. It was perfect."
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
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
Tranquility Cottage | 3 Bed, 1.5 Bath
9.0 out of 10, Wonderful, (9)
"We loved our time at the house. It had everything we needed for a relaxing weekend."
Tranquility Cottage | 3 Bed, 1.5 Bath
'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'
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, (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 !
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (118)
"The cabin is beautiful and fully equipped with everything we needed. It was very clean and had a cozy atmosphere. The back deck and fire pit were very nice. We loved everything about it!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (317)
"This cabin is beautiful and very secluded. Check in process and communication with owner doesnt get any easier. We'll be back next year."
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
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.