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Compare 42 Vacation Homes in Winchester with updated reviews, rates, and availability.

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.6 out of 10, Exceptional, (5)
"My father, husband, children (21, 16), their two friends (19, 18) and myself all immensely enjoyed our stay. We grew up in neighboring Henry County, so we were somewhat familiar with this area even though we had not been here in several years. We needed accommodations as we had a family wedding to attend this particular weekend, and the property was absolutely perfect for us to stay the weekend and beyond. Nestled into the woods, we enjoyed the comforts of tranquility and privacy, along with...
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (55)
"Our family was very pleased with this property. It was convenient, clean and comfortable. Just what we needed to spend a few days with family over Thanksgiving. We definitely would consider booking again. "
5 min walk to BSU Campus - Quiet Neighborhood

Retro Home Close to Campus

The price is AED 441
AED 1,020 total
includes taxes & fees
26 Dec - 27 Dec
Retro Home Close to Campus

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

10.0 out of 10, Exceptional, (177)
"Very clean beautiful house great layout the gym was in constant use basketball volleyball and pickleball will definitely go back "
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

Beautiful 2 bedroom house -Close to IU Health Hospital & Ball State University

10.0 out of 10, Exceptional, (14)
"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."
Beautiful 2 bedroom house -Close to IU Health Hospital & Ball State University

Recently remodeled Colonial-style home with room for the whole family!

10.0 out of 10, Exceptional, (30)
"We found this home to be very well supplied and clean. It was just the perfect place for us to gather for Thanksgiving. Its very comfy-cozy and in a nice neighborhood. The only thing of note is that the upstairs bathroom fan is noisy and we were not left towel sets for the shower in the downstairs bath. However, since there's a washer and dryer, we just washed towels to fix that. Would highly recommend this home."
Recently remodeled Colonial-style home with room for the whole family!

Boho Bungalow off Main-one block from Lovely Park

9.4 out of 10, Exceptional, (6)
"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."
Boho Bungalow off Main-one block from Lovely Park

Exquisite Hagerstown Home with Deck & Gazebo!

10.0 out of 10, Exceptional, (4)
"This property was fantastic and had all the amenities we were looking for in a long weekend away. "
Exquisite Hagerstown Home with Deck & Gazebo!

The University House King Beds+Fast WIFI+W/D

10.0 out of 10, Exceptional, (2)
"Loved all the space & the fact that it was child friendly!"
The University House King Beds+Fast WIFI+W/D

3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table

3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table

Westcott Mansion with Pickleball Court & Huge Gazebo

10.0 out of 10, Exceptional, (26)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
The price is AED 606
AED 1,222 total
includes taxes & fees
23 Dec - 24 Dec
Westcott Mansion with Pickleball Court & Huge Gazebo

La Dolce Vita

2.0 out of 10, (2)
"The pictures uploaded are either very old, or doctored. Bed sheets had stains on them with black light. Cameras installed throughout the inside of the home. No running water when we arrived. We checked into a motel, and then owner tried to charge me $2000.00 for "water damage", when there was no running water and we never stayed."
The price is AED 661
AED 938 total
includes taxes & fees
23 Dec - 24 Dec
La Dolce Vita

country home with hot tub close to town

9.0 out of 10, Wonderful, (33)
"Had Thanksgiving with the family, lots of room. Love the quiet surroundings "
country home with hot tub close to town

Cardinal Cottage - 2 bedroom cozy home

9.4 out of 10, Exceptional, (8)
"This was a great house! Many upgrades and personal touches. Loved the well stocked kitchen - even though we didn't need it this time! We will come back soon!"
The price is AED 367
AED 658 total
includes taxes & fees
23 Dec - 24 Dec
Cardinal Cottage - 2 bedroom cozy home

3 br country home close to town with hot tub

9.4 out of 10, Exceptional, (24)
"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."
3 br country home close to town with hot tub

Elegant House 2 min from BSU/Hospital/Downtown

9.4 out of 10, Exceptional, (3)
"Property worked great for visiting family in Yorktown. House was very clean and very welcoming for guests. Traffic on the main drag was a bit heavy at times and also at above average rate of speeds making it somewhat worrisome when having to get to our vehicles with smaller children in our group. Certainly fit our needs and have no complaints. Thanks Roman."
The price is AED 770
AED 1,862 total
includes taxes & fees
29 Dec - 30 Dec
Elegant House 2 min from BSU/Hospital/Downtown

!Country Home Get Away! !Private Backyard!

10.0 out of 10, Exceptional, (12)
"Great time "
!Country Home Get Away! !Private Backyard!

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (19)
"The house was as we expected. Very well decorated and very clean. We felt safe and comfortable. "
Pet-Friendly Greenville Home w/ Private Yard

2 Bedroom Retreat near Earlham College in Richmond IN

10.0 out of 10, Exceptional, (25)
"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! "
2 Bedroom Retreat near Earlham College in Richmond IN

Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

7.0 out of 10, Good, (4)
"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."
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie
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.
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Other property types in Winchester

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

10.0 out of 10, Exceptional, (177)
"Very clean beautiful house great layout the gym was in constant use basketball volleyball and pickleball will definitely go back "
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (55)
"Our family was very pleased with this property. It was convenient, clean and comfortable. Just what we needed to spend a few days with family over Thanksgiving. We definitely would consider booking again. "
5 min walk to BSU Campus - Quiet Neighborhood

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.6 out of 10, Exceptional, (5)
"My father, husband, children (21, 16), their two friends (19, 18) and myself all immensely enjoyed our stay. We grew up in neighboring Henry County, so we were somewhat familiar with this area even though we had not been here in several years. We needed accommodations as we had a family wedding to attend this particular weekend, and the property was absolutely perfect for us to stay the weekend and beyond. Nestled into the woods, we enjoyed the comforts of tranquility and privacy, along with...
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
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.