Winchester Vacation Rentals

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Browse Select Winchester Vacation Homes

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Fridge, microwave, oven, stovetop
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
10.0 out of 10, Exceptional, (172)
"Had a Great time!!! Would definitely recommend going here. Everything was just how the listing said. "
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
5 min walk to BSU Campus - Quiet Neighborhood
Property grounds
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
Fridge, microwave, stovetop, dishwasher
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
3 br country home close to town with hot tub
Fridge, microwave, oven, stovetop
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
Cardinal Cottage - 2 bedroom cozy home
Exterior
Cardinal Cottage - 2 bedroom cozy home
9.0 out of 10, Wonderful, (6)
"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 CA $135
CA $241 total
includes taxes & fees
Sep 29 - Sep 30
Cardinal Cottage - 2 bedroom cozy home
2 Bedroom Retreat near Earlham College in Richmond IN
Outdoor dining
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
Quaint Economy Retreat w/ Patio & Spacious Yard!
Fridge, microwave, stovetop, coffee/tea maker
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!
3 Bedroom House in Fort Recovery
Fridge, microwave, oven, stovetop
3 Bedroom House in Fort Recovery
10.0 out of 10, Exceptional, (17)
"This property had everything & more that we needed for our stay. Very friendly community, easy walking through town."
3 Bedroom House in Fort Recovery
Boho Bungalow off Main-one block from Lovely Park
Fridge, microwave, oven, stovetop
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 CA $118
CA $231 total
includes taxes & fees
Oct 13 - Oct 14
Boho Bungalow off Main-one block from Lovely Park
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Cookware/dishes/utensils
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!
Property grounds
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 Home! Prime Location! Dog-Friendly!
Property grounds
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 CA $236
CA $472 total
includes taxes & fees
Sep 28 - Sep 29
Charming Home! Prime Location! Dog-Friendly!
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 CA $241
CA $275 total
includes taxes & fees
Sep 30 - Oct 1
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Westcott Mansion with Pickleball Court & Huge Gazebo
8 bedrooms, WiFi, bed sheets
Westcott Mansion with Pickleball Court & Huge Gazebo
10.0 out of 10, Exceptional, (22)
"We have a group of our closest friends and family stay for my 30th birthday. We had a blast. The house is absolutely beautiful. "
The price is CA $195
CA $412 total
includes taxes & fees
Sep 30 - Oct 1
Westcott Mansion with Pickleball Court & Huge Gazebo
La Dolce Vita
Private kitchen
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 CA $242
CA $344 total
includes taxes & fees
Sep 28 - Sep 29
La Dolce Vita
country home with hot tub close to town
Fridge, microwave, oven, stovetop
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
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
Fridge, microwave, oven, stovetop
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 CA $218
CA $605 total
includes taxes & fees
Sep 30 - Oct 1
Elegant House 2 min from BSU/Hospital/Downtown
!Country Home Get Away! !Private Backyard!
Fridge, microwave, oven, stovetop
!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
Fridge, microwave, stovetop, dishwasher
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
Don't see what you're looking for?
See all available properties in Winchester
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
Fridge, microwave, oven, stovetop
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
10.0 out of 10, Exceptional, (172)
"Had a Great time!!! Would definitely recommend going here. Everything was just how the listing said. "
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
5 min walk to BSU Campus - Quiet Neighborhood
Property grounds
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
Fridge, microwave, stovetop, dishwasher
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.