Search Vacation Homes in Winchester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 30 Vacation Homes in Winchester with updated reviews, rates, and availability.

Beautiful Rocky Fork 2BR Cozy Cottage
10.0 out of 10, Exceptional, (88)
"Very high standard accommodation. Very clean and comfortable and in a great location. Would definitely come back."
Beautiful Rocky Fork 2BR Cozy Cottage
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
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
Save an average of 15% on thousands of hotels when you're signed in
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
9.8 out of 10, Exceptional, (119)
"Awesome quiet with a Pileated and a whippoorwill chorus."
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
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
URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.8 out of 10, Exceptional, (15)
"The property was great! Good location for me."
The price is SAR 296
SAR 455 total
includes taxes & fees
12 Jum. II - 13 Jum. II
URBAN GETAWAY - .6 Downtown Maysville/Entire House
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
10.0 out of 10, Exceptional, (4)
"Excellent stay. The property was clean and updated. Plenty of room for a big family. The home is offset in the woods giving excellent privacy. Great backyard area with a pond. The hosts were very responsive to all my questions and check-in and check-out were easy. We were very satisfied with our stay and would stay again without question."
Secluded home away
'Small Town Getaway'
10.0 out of 10, Exceptional, (4)
"Amazing place to stay!"
'Small Town Getaway'
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (12)
"We had a great weekend. The owner was very responsive and the house and property was beautiful."
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (12)
"This allowed all my brothers and sister along with grandchildren to enjoy each others company!!"
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
LAKE HOUSE ON ROCKY FORK!
9.2 out of 10, Wonderful, (15)
"Brought the kids down for spring break had an excellent time"
LAKE HOUSE ON ROCKY FORK!
The Steampunk Hideaway
The price is SAR 413
SAR 812 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Steampunk Hideaway
Beautifully renovated unit in the downtown Maysville’s entertainment district
10.0 out of 10, Exceptional, (31)
"Was a great location for us. View was great. We will stay again"
Beautifully renovated unit in the downtown Maysville’s entertainment district
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
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 Getaway on Ohio River Scenic Byway
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
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
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
Don't see what you're looking for?
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 !
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 !
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (96)
"This cabin stay was great! Cabin is beautiful, seemed brand new, and was very clean. There is a lovely big patio that we spent most of our time on! Lots of great hikes nearby. Highly recommend!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
The Bear Den (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (16)
"Everything was wonderful!"
The price is SAR 394
SAR 638 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Bear Den (Secluded in Amish Country and peaceful)
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