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Compare 41 Vacation Homes in Winchester with updated reviews, rates, and availability.

Interior of Gym- Basketball, Volleyball, Pickleball, Dodgeball

"Our family tries to get together at least once each year, normally around the Christmas holiday. We (2 grandparents, 8 children and spouses, and 15 grandchildren ages 7 to 30) came to this Ft Recovery gem from Ohio, Illinois, New York, Los Angeles and Virginia. The main floor open kitchen, living room and eating spaces, game area in the lower floor, and fantastic adjacent building with full basketball/volleyball court and loft with wet bar allowed us to spread out and spend time in small groups...

"The house was just as describedThe host was great and quickly responded with when i had questions. We arrived to find a nice note and home baked cookies. The berries was great and it was very spacious for our large group. Definitely recommend"

Economy Vacation Rental | 3BR | 2BA | 1,418 Sq Ft | 3 Steps to Enter

"This property is maintained very well and is clean. Three people stayed and there was more than enough room. The owners were very responsive and accommodating. We would recommend this property and owner. "

"We stayed for the weekend at the Westport mansion to celebrate two of our sisters’ big milestone birthdays. The five of us each had our own rooms in this beautiful home. It is surprisingly quiet given the house is just a block off a busy road. The neighborhood was quiet and we were just minutes from pretty much everything in town. The place is so big, with so many beautiful sitting rooms that we joked we should set a timer and move to a different place to hang out every 30 minutes. Some times at...

AED 1,222 total

includes taxes & fees

20 Feb - 21 Feb

"Great place, very clean and very nice house. Worked well for a large number of people. "

"Wasn't sure about the neighborhood at first but we had zero issues. House is a bit dated and the front bedroom smelled of smoke. When we arrived there were no towels or washcloths and the bathroom sink was very slow to drain. Messaged the property owner and everything was taken care of within an hour!! EXCELLENT customer service! Overall not a bad experience and it was very convenient to my activity."

"We traveled to Muncie for a family wedding and were so happy to have found Kyle and Shannah’s place. It was clean, in a quiet neighborhood, and close to Ball State. The hosts were quick and easy to communicate with! We would happily stay there again."

"We really enjoyed our stay here, what a lovely home. "

"We loved the home along with all of the amenities. If your contemplating on which house to stay in choose this one! Cindy provided so many extras! From blankets, towels, kitchen dishes to seasonings & even the basic “staples” in the refrigerator along w snacks. Very beautiful home with character . Thankyou opening your home up to us . We will return! "

"My husband, son, and I stayed here the weekend of our daughter’s graduation from Miami University. It was so cute and easy to access. The communication was awesome and check in/check out process was simple. Would definitely recommend."

AED 658 total

includes taxes & fees

20 Feb - 21 Feb

Hagerstown Vacation Rental | 3BR | 3.5BA | 1 Step to Enter | 1,800 Sq Ft

"This property was fantastic and had all the amenities we were looking for in a long weekend away. "

"Cutest cottage and fabulous hosts went above and beyond for us! Thank you Cole and Margee!"

AED 658 total

includes taxes & fees

17 Feb - 18 Feb

"Perfect place for our needs. Spacious house, only 15 minutes from our destination, Muncie. The ONLY knock on the place is that it is a little dated especially the bathrooms which need to be updated."

AED 1,172 total

includes taxes & fees

14 Mar - 15 Mar

Greenville Vacation Rental | 3BR | 1BA | Stairs Required | 1,058 Sq Ft

"The house was as we expected. Very well decorated and very clean. We felt safe and comfortable. "

King Bedroom - Very Large! Room for a blow up mattress (provided) on the floor.

"Great time "

"The house exceeded our expectations. Plenty of room, very clean, comfortable beds, comfortable furniture, and a huge TV to watch the game on. There is also a big game room. The host, Matt, was easy to work with and communicated promptly. If you are in the area, don't hesitate to rent this lovely home."

AED 749 total

includes taxes & fees

24 Feb - 25 Feb

"This was an amazing welcome getting to the house and it was more than I ever expected. Amenities were great and the host was very gracious!"

"We thoroughly enjoyed our stay. Mara was very communicative and the house was very cozy and charming. It was a delight to walk around the neighborhood and see all the beautiful historic homes. Our group of 5 adults had a great stay and we were able to bring our dog, which was great!"

AED 1,296 total

includes taxes & fees

17 Feb - 18 Feb

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Other property types in Winchester

"This was a great place to stay. We were in town for a concert in indy and everything in indy was a fortune. We found this place a little outside of indy but not too far. The place is amazing and beautiful. The decor fits it real.well the exposed rafters i love. Its kind of a vintage feel. I told my daughter when we got there i loved the place so much im not leaving. She told me i have to because she plans on not leaving. Plenty of food and dining just a mile or two away. I dont know if ill...