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

Beautiful Rocky Fork 2BR Cozy Cottage
Welcome to Blue Heaven Cottage
Beautiful Rocky Fork 2BR Cozy Cottage
10.0 out of 10, Exceptional, (89)
"Thought would be closer to Lake Nothing we had marked was open during the week Was still great relaxing adventure."
Beautiful Rocky Fork 2BR Cozy Cottage
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, (13)
"For the last four years, we have a family weekend with 14-18 people. We've rented a different place every year. This has been by far the best place for our group. The place really is massive. We could have comfortably fit another 4-6 people. Instead of people sleeping 4 in a room, each group had their own space. The common areas are large, and there's a nice outdoor area with a fire pit. If you have a large group, it doesn't get much better than this. The only con is really that it's close to...
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
2800 sq. ft. 3-level Home, bordering Thousands of acres of Brush Creek Forest
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
9.8 out of 10, Exceptional, (120)
"We really enjoyed ourselves. Turn off the electronics and appreciate mother nature! Comfy beds and anything else you might need for a relaxing getaway."
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
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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, (55)
"Our 2nd Fall stay here and another great time!! 16 guys and plenty of room for all. Great yard space for cornhole & can jam. Love the fire ring. Some rain our last night, but plenty of room inside for card games. GREAT PLACE!! GREAT DEAL!!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Urban Getaway front porch - 535 Forest Av.
URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.8 out of 10, Exceptional, (16)
"We had everything we needed, and enjoyed the house a lot! The house is beautiful, while still keeping its old charm."
The price is AED 290
AED 446 total
includes taxes & fees
13 Jun - 14 Jun
URBAN GETAWAY - .6 Downtown Maysville/Entire House
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, (13)
"This has been an outstanding property for our annual family vacation! Beautiful setting, spacious house with lots of extras, outdoor kitchen/patio. The owners are very responsive and thoughtful! This was our second stay, and we will be back next year."
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
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, (21)
"The home is Beautiful. Everything a family needs is there. Board games, darts, karaoke, corn hole, and steaming TV services. The location is convenient to local attractions. The two individual cabins are very cozy and well appointed. We had a couple small issues that the hosts took care of immediately. A bathroom in the upstairs of the home would be a great addition. We would highly recommend this property."
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Peaceful Country Retreat 20 acres Private Pond
Exterior
Peaceful Country Retreat 20 acres Private Pond
10.0 out of 10, Exceptional, (14)
"my family and i had a great stay plenty of room for everyone. if you're looking for a quiet getaway this is the place you want to be."
Peaceful Country Retreat 20 acres Private Pond
Secluded home away
Exterior
Secluded home away
10.0 out of 10, Exceptional, (4)
"Property was super clean, quaint, quiet, backyard was amazing with the pond and the big trees and beautiful forest in the background. What a serene view. Had all the amenities we could ask for. Plus a pool table! Will definitely stay again. The host also let us have a little bit of a late check out, which was very nice, and they did not have to do that"
Secluded home away
'Small Town Getaway'
Property grounds
'Small Town Getaway'
10.0 out of 10, Exceptional, (4)
"Amazing place to stay!"
'Small Town Getaway'
Relax and Unwind at River Front Oasis w/ Hot Tub
Living area
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
LAKE HOUSE ON ROCKY FORK!
LAKE HOUSE ON ROCKY FORK!
9.2 out of 10, Wonderful, (16)
"The house was spacious and the property was also with plenty of room inside and outside too. Close to the boat ramps, gas stations and several eating locations. The kitchen was very well stocked for us to cook several meals and was equipped with what was needed. The beds were comfortable and each room had a nice down home feeling as the house was nice and clean. Indoor seating options, sunroom and also seating outside on the patio or front porch, plenty of space. The Bathrooms were nice and...
LAKE HOUSE ON ROCKY FORK!
The Steampunk Hideaway
Interior
The Steampunk Hideaway
6.0 out of 10, (1)
"Needs some attention. Lose the plastic sheets over the mattress. Hard to sleep every time we moved it would wake us up. Need a luggage rack so suitcase doesn’t have to sit on floor. AC doesn’t keep up in keeping bedroom cool. Add a couple towel hooks in bathroom. VRBO website difficult. POSITIVE: Quiet, easy to get to, good parking, has all the basics you would need. Needs a few improvements but overall for location not too bad."
The price is AED 404
AED 792 total
includes taxes & fees
13 Jun - 14 Jun
The Steampunk Hideaway
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, (32)
"Excellent renovationed property. Roomy, clean and stocked well. Great view of the Ohio River. Perfect located for getting around downtown!"
Beautifully renovated unit in the downtown Maysville’s entertainment district
Robin Hill | 3 Bed, 2.5 Bath
Interior
Robin Hill | 3 Bed, 2.5 Bath
9.2 out of 10, Wonderful, (14)
"Great location peaceful plenty of room!!"
Robin Hill | 3 Bed, 2.5 Bath
Luxurious & Modern newly renovated good for corporate housing & family functions
Exterior
Luxurious & Modern newly renovated good for corporate housing & family functions
9.0 out of 10, Wonderful, (2)
"Host very attentive, Very clean place. we used for wedding weekend. comfortable for large family."
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
Manchester Getaway on Ohio River Scenic Byway
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!
10.0 out of 10, Exceptional, (1)
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!
Tranquility Cottage | 3 Bed, 1.5 Bath
Interior
Tranquility Cottage | 3 Bed, 1.5 Bath
9.8 out of 10, Exceptional, (8)
"We loved our time at the house. It had everything we needed for a relaxing weekend."
Tranquility Cottage | 3 Bed, 1.5 Bath
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, (16)
"Perfect size and location for our getaway. The gameroom was great for the kids, great fire pit for the adults. Close to all that Rocky Fork has to offer."
Beautifully renovated 3BR house w/lake views
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See all available properties in Winchester
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.

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, (240)
"It was perfect for the event we were attending! The hosts were amazing and the property is beautiful! Next time we stay we are going to stay an extra day so we can enjoy it a bit more!! Thank you for allowing our bosties to come with us, they had a blast!"
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!
Early 1800's cabin completely remodeled with modern conveniences.
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (308)
"This is a wonderful property. Quiet, serene, spotless, welcoming."
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 .
Real authentic log cabin
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (96)
"Some previous coworkers and I spent three days together at the cabin for some much-needed rest and relaxation. The place is beautiful and has everything you would need. We made good meals. Took some trips into the area and did some nice hikes. Mostly just relax at the cabin, which is lovely. Won’t be disappointed."
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.

Recent reviews of Winchester hotels
Expedia verified reviews

Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

5/5 Excellent
"Very friendly staff. "
A verified traveler stayed at Super 8 by Wyndham Maysville KY
Posted 3 days ago
Super 8 by Wyndham Maysville KY