
Vacation rentals in Winchester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Top guest favourite

Home in Chillicothe
4.98 out of 5 average rating, 49 reviewsFive bedroom family home with pool and hot tub
ChrisRating, 5 stars2 weeks ago
My team stayed in Beth's house for the Buck Fifty race and it was perfect. Plenty of room for us to spread out, hot tub for sore muscles after each portion of the race and a comfortable place to relax in during the downtime. We will absolutely be booking for the race again next year assuming someone else doesn't snag it out from under us.
Guest favourite

Home in Peebles
4.9 out of 5 average rating, 39 reviewsHarvest Haven Grain Bin
RitaRating, 5 stars1 week ago
If you’re looking for a peaceful little getaway, this is the place for you from the kitchen to the bedroom. Everything was squeaky clean and very nicely decorated. We enjoyed grilling and spending time in the hot tub. You can hear traffic noises when you are outside, but that did not bother us. All in all it was the perfect place to celebrate our anniversary. I would definitely recommend this place to anyone!!
Superhost

Home in Flemingsburg
4.67 out of 5 average rating, 3 reviewsLazy Lake Cabin #2 Pet Friendly
JamesRating, 5 stars9 months ago
If you’re looking for boujee, this is not for you. If you’re looking for a nice cabin to relax in, a very beautiful outdoor camp-like atmosphere, with a lake right outside the door - BINGO! This is it!! If you forgot something, just drive down the road to a store, walmart, and even a bait shop. If you want to go out to eat, there are restaurants near by for breakfast, lunch or dinner! Overall, this was a great experience with a super nice Host! We will definitely be back!
Top guest favourite

Home in Winchester
5 out of 5 average rating, 39 reviewsWelcome to Dancing Deer Acres!
MeganRating, 5 stars3 months ago
Bob and Sherry’s place was spacious, comfortable, felt private and peaceful. The kitchen was well stocked, which is always very important to me. We definitely plan to visit again when in the area.
Top guest favourite

Home in Berry
5 out of 5 average rating, 19 reviewsPeacock House
SarahRating, 5 stars1 week ago
Absolutely loved our stay at the peacock house. The perfect house for a larger group with plenty of space for everyone. We came to Kentucky for the Ark and Creation Museum and this house was in the perfect spot. Close enough to the attractions but also tucked away in the country where it was peaceful and quiet. If you need a home with more than four bedrooms this one is a great choice!
Superhost

Cabin in Bentonville
4.85 out of 5 average rating, 39 reviewsHopewell Croft - Peaceful Cabin
SpencerRating, 5 stars6 months ago
Loved our time here! The house was as advertised, spacious, lots of amenities for kiddos and adults. Comfortable beds. Clean. Very quiet and the bedrooms were DARK in the morning with all the trees. Lovely cabin in the woods.
Guest favourite

Home in Peebles
4.92 out of 5 average rating, 38 reviewsPeaceful 8 Bedroom 5 Bath w/patio bar-grill
MatthewRating, 5 stars1 week ago
Great place in a scenic location with a lot of space both inside and outside and lots of great utilities such as the barbecue, basketball hoop, and games like pool and air hockey!
Guest favourite

Home in Milford
5 out of 5 average rating, 6 reviewsRiver House on 5 Acres w/ Kayaks
AlexRating, 5 stars1 month ago
Definitely would go again made a great place for a family vacation, 1 bathroom was the only negative for multiple families.
Destinations to explore
- Columbus Vacation rentals
- Cincinnati Vacation rentals
- Lexington Vacation rentals
- Dayton Vacation rentals
- Red River Gorge Vacation rentals
- Williamstown Vacation rentals
- Frankfort Vacation rentals
- Covington Vacation rentals
- Nashville Vacation rentals
- Gatlinburg Vacation rentals
- Chicago Vacation rentals
- Western North Carolina Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Great American Ball Park
- Cincinnati Music Hall
- Kings Island
- Cincinnati Zoo & Botanical Garden
- Carter Caves State Resort Park
- Newport Aquarium
- East Fork State Park
- Paint Creek State Park
- Cowan Lake State Park
- National Underground Railroad Freedom Center
- Coney Island Park
- Smale Riverfront Park
- Caesar Creek State Park
- Krohn Conservatory
- Cincinnati Art Museum
- Camargo Club
- Contemporary Arts Center