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Compare 37 Vacation Homes in Winchester with updated reviews, rates, and availability.

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Interior of Gym- Basketball, Volleyball, Pickleball, Dodgeball
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
10.0 out of 10, Exceptional, (172)
"The trip was absolutely amazing. It's a beautiful property. While the listing pictures are beautiful, we were all stunned when seeing the home, surrounding land, and gymnasium! They have everything you could need. Best place I've stayed in!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Charming 2 bedroom house -Close to IU Health Hospital & Ball State University
Living room with 65" tv
Charming 2 bedroom house -Close to IU Health Hospital & Ball State University
10.0 out of 10, Exceptional, (13)
"I came back to Muncie to visit family and friends. The house was clean and conveniently located to West McGalliard, which is close to a lot of restaurants. I will definitely stay here the next time I'm in town vs staying in a hotel. I discovered Parlor Doughnuts, which is very close to this property. Perhaps a little too close. I gained 3 pounds on this extended weekend trip. "
Charming 2 bedroom house -Close to IU Health Hospital & Ball State University
Charming Home! Prime Location! Dog-Friendly!
Exterior
Charming Home! Prime Location! Dog-Friendly!
9.4 out of 10, Exceptional, (3)
"Clean, nice, Bar-B-Q grill and utensils, good mix of pots, pans, utensils, plates, silver where. Overall a great experience "
The price is SAR 657
SAR 1,315 total
includes taxes & fees
23 Sep - 24 Sep
Charming Home! Prime Location! Dog-Friendly!
Cardinal Cottage - 2 bedroom cozy home
Exterior
Cardinal Cottage - 2 bedroom cozy home
9.2 out of 10, Wonderful, (5)
"arrived at around 4pm, went to concert, came back, shower, bed time. i sleep cozy. lovely place. definitely would come back! 10/10"
The price is SAR 375
SAR 672 total
includes taxes & fees
24 Sep - 25 Sep
Cardinal Cottage - 2 bedroom cozy home
!Country Home Get Away! !Private Backyard!
King Bedroom - Very Large! Room for a blow up mattress (provided) on the floor.
!Country Home Get Away! !Private Backyard!
10.0 out of 10, Exceptional, (11)
"Was amazing with highly recommend especially anyone wanting to attend races at eldora"
!Country Home Get Away! !Private Backyard!
Pet-Friendly Greenville Home w/ Private Yard
Greenville Vacation Rental | 3BR | 1BA | Stairs Required | 1,058 Sq Ft
Pet-Friendly Greenville Home w/ Private Yard
10.0 out of 10, Exceptional, (17)
"We stayed here for 3 night with our two dogs. The house was very well decorated. The kitchen was well stocked with pots, pans, cooking utensils, they even supplied k-cup for your morning coffee. Looking forward to staying here again for longer."
Pet-Friendly Greenville Home w/ Private Yard
2 Bedroom Retreat near Earlham College in Richmond IN
Property grounds
2 Bedroom Retreat near Earlham College in Richmond IN
10.0 out of 10, Exceptional, (22)
"The property was very clean, had everything we needed, perfect size, location was great (our son goes to Earlham), and the property manager answered our questions quickly! I would absolutely recommend this house!"
2 Bedroom Retreat near Earlham College in Richmond IN
Boho Bungalow off Main-one block from Lovely Park
Room
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."
The price is SAR 329
SAR 642 total
includes taxes & fees
13 Oct - 14 Oct
Boho Bungalow off Main-one block from Lovely Park
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Richmond Vacation Rental | 2BR | 1.5BA | 2 Steps Required | 960 Sq Ft
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
10.0 out of 10, Exceptional, (1)
" I loved my stay and really enjoyed being out in the country. It was quiet and everything was perfect. Even got to chat with the little colt next door as he came up to the fence to say hello. I will definitely be back with my next stay in Indiana."
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Exquisite Hagerstown Home with Deck & Gazebo!
Hagerstown Vacation Rental | 3BR | 3.5BA | 1 Step to Enter | 1,800 Sq Ft
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!
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Exterior
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
2.0 star property
2.0 out of 10, (1)
"Didn’t get in the house"
The price is SAR 672
SAR 766 total
includes taxes & fees
23 Sep - 24 Sep
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Westcott Mansion with Pickleball Court & Huge Gazebo
Room
Westcott Mansion with Pickleball Court & Huge Gazebo
10.0 out of 10, Exceptional, (21)
"We enjoyed exploring the Mansion. It was a beautiful house and nice grounds."
The price is SAR 544
SAR 1,147 total
includes taxes & fees
23 Sep - 24 Sep
Westcott Mansion with Pickleball Court & Huge Gazebo
La Dolce Vita
Room
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 SAR 675
SAR 958 total
includes taxes & fees
23 Sep - 24 Sep
La Dolce Vita
5 min walk to BSU Campus - Quiet Neighborhood
Room
5 min walk to BSU Campus - Quiet Neighborhood
10.0 out of 10, Exceptional, (50)
"I was very nice, clean and quiet, just was we needed for some down time for our daughters wedding"
5 min walk to BSU Campus - Quiet Neighborhood
country home with hot tub close to town
fenced in front yard
country home with hot tub close to town
8.8 out of 10, Excellent, (29)
"We liked the location, and our dog liked it too. The front yard is picket fenced, there is NOT a chain fence in back as shown on the listing. Beds were comfy."
country home with hot tub close to town
3 br country home close to town with hot tub
one car garage
3 br country home close to town with hot tub
9.6 out of 10, Exceptional, (20)
"The location was only about 20 mins away from the venue. It was perfect for what we needed and very well stocked. Thank You "
3 br country home close to town with hot tub
Recently remodeled Colonial-style home with room for the whole family!
Exterior
Recently remodeled Colonial-style home with room for the whole family!
10.0 out of 10, Exceptional, (25)
"We stayed with extended family for an event in the area. The house was beautiful and very clean. It has a mix of modern and vintage touches. The beds were comfortable. I only wished we had "
Recently remodeled Colonial-style home with room for the whole family!
Elegant House 2 min from BSU/Hospital/Downtown
Living area
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 SAR 612
SAR 1,686 total
includes taxes & fees
25 Sep - 26 Sep
Elegant House 2 min from BSU/Hospital/Downtown
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie
Living area
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie
7.0 out of 10, Good, (4)
"Clean. Approximately priced. Didn’t like cigarette smoke smell. Not impressed with renovation. Close to restaurants,etc. I do recommend & would stay here again."
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie
Quaint Economy Retreat w/ Patio & Spacious Yard!
Economy Vacation Rental | 3BR | 2BA | 1,418 Sq Ft | 3 Steps to Enter
Quaint Economy Retreat w/ Patio & Spacious Yard!
9.0 out of 10, Wonderful, (4)
"We were attending a funeral in Farmland and this was the perfect location. No frills. Just what you need. Comfy place to sleep. Serene farm setting. Would stay here again if we need to."
Quaint Economy Retreat w/ Patio & Spacious Yard!
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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
Interior of Gym- Basketball, Volleyball, Pickleball, Dodgeball
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
10.0 out of 10, Exceptional, (172)
"The trip was absolutely amazing. It's a beautiful property. While the listing pictures are beautiful, we were all stunned when seeing the home, surrounding land, and gymnasium! They have everything you could need. Best place I've stayed in!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
5 min walk to BSU Campus - Quiet Neighborhood
Room
5 min walk to BSU Campus - Quiet Neighborhood
10.0 out of 10, Exceptional, (50)
"I was very nice, clean and quiet, just was we needed for some down time for our daughters wedding"
5 min walk to BSU Campus - Quiet Neighborhood
Charming 2 bedroom house -Close to IU Health Hospital & Ball State University
Living room with 65" tv
Charming 2 bedroom house -Close to IU Health Hospital & Ball State University
10.0 out of 10, Exceptional, (13)
"I came back to Muncie to visit family and friends. The house was clean and conveniently located to West McGalliard, which is close to a lot of restaurants. I will definitely stay here the next time I'm in town vs staying in a hotel. I discovered Parlor Doughnuts, which is very close to this property. Perhaps a little too close. I gained 3 pounds on this extended weekend trip. "
Charming 2 bedroom house -Close to IU Health Hospital & Ball State University
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.