
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
Guest favorite

Home in Hillsboro
5 out of 5 average rating, 41 reviewsRoute 50 Retreat - Unit A
JanaRating, 5 stars2 days ago
Lovely bungalow with plush towels & bedding in a pleasing retro Decor . Excellent kitchen with thoughtful touches for cooking in . We didn’t get to explore the area due to time but the heathy grocery & charming coffee/pastry shop are wonderful . Jill has great taste & is an excellent host
Guest favorite

Cabin in Blue Creek
4.97 out of 5 average rating, 32 reviewsHistoric log cabin getaway!
MinnieRating, 5 stars1 week ago
The cabin and property were both so peaceful and absolutely stunning. We wished we could have stayed longer. Everything was clean and the kitchen had all nice new amenities. We will definitely recommend this property and hope we can come back! Thank you
Guest favorite

Home in Peebles
4.9 out of 5 average rating, 40 reviewsHarvest Haven Grain Bin
RitaRating, 5 stars1 month 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!!
Top guest favorite

Tiny home in Winchester
5 out of 5 average rating, 9 reviewsHighland Hideout
AshleyRating, 5 stars2 weeks ago
We loved it !! i It was perfect on all levels. Loved the cow theme and the cows outside. Definitely recommend!! If we are in the area again we would definitely stay again.

Home in Sardinia
4.86 out of 5 average rating, 222 reviewsPrivate Getaway|20 Acres | Pond & Fire Pit |Pets
CalebRating, 5 stars1 month ago
We had a great time here the only thing we had a small problem with was the age of the TVs. They were mid 2000s but absolutely was manageable. We will 100% be back soon for another events
Top guest favorite

Place to stay in Ripley
4.99 out of 5 average rating, 98 reviewsJail Break Inn in Downtown Ripley
NancyRating, 5 stars4 weeks ago
We loved this Airbnb! Missy made sure to leave so many thoughtful touches throughout the house! The house was so clean and had such a beautiful decor. The game room was an absolute hit! We loved playing pool and ping pong. Our family had a blast. The living room was so comfortable and relaxing. The area surrounding the home was so quaint - It was a lovely piece of Americana. We loved taking a walk to the river and visiting shops along the way. A wonderful stay!
Guest favorite

Tiny home in New Richmond
4.95 out of 5 average rating, 73 reviewsHagrid's Hut - Harry Potter Riverfront Experience
ZachRating, 5 stars6 days ago
This is a very nice cottage and setting on the Ohio River. We absolutely loved the outdoor gathering space. The hosts are very friendly and responsive. We would recommend this place to others!
Top guest favorite

Cabin in Foster
4.98 out of 5 average rating, 60 reviewsRiver Refuge Retreat
JulieRating, 5 stars3 weeks ago
Beautiful cozy cabin atop private property offering beautiful views of the Ohio River by day and bright stars on a clear night. If you get a foggy sunrise along the river valley followed by the most sunny day ever, take a scenic drive along the river to Augusta, KY for a foodie's paradise and then to Vanceburg, and so on because there's so many wonderful small Kentucky river towns full of history and adventures awaiting for you. Slow down for the deer and chipmunks!!! Enjoy your visit to this beautiful and peaceful cabin.
Destinations to explore
- Columbus Vacation rentals
- Cincinnati Vacation rentals
- Lexington Vacation rentals
- Dayton Vacation rentals
- Williamstown Vacation rentals
- Red River Gorge Vacation rentals
- Frankfort Vacation rentals
- Logan 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
- Kings Island
- Cincinnati Zoo & Botanical Garden
- Carter Caves State Resort Park
- East Fork State Park
- Newport Aquarium
- Smale Riverfront Park
- Cincinnati Music Hall
- Paint Creek State Park
- Caesar Creek State Park
- Cowan Lake State Park
- National Underground Railroad Freedom Center
- Coney Island Park
- Cincinnati Art Museum
- Camargo Club
- Contemporary Arts Center
- Krohn Conservatory