Winchester Holiday Rentals

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Check prices for these dates

Tonight
1 Nov - 2 Nov
Tomorrow
2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Holiday Rentals in Winchester

Outdoor dining
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
9.8 out of 10, Exceptional, (196)
"Had a great time. Location is excellent and really enjoyed everything the house had to offer. "
United States
Cade P.
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
A heated pool
Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25
Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25
10.0 out of 10, Exceptional, (201)
"We loved staying here, it was an incredible trip with amazing amenities!"
United States
Carmen O.
Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25
Exterior
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Quaker Hill Cottage on gated estate with fire pit & hiking trails
9.8 out of 10, Exceptional, (25)
"Such an interesting place. It was a great stay. We would definitely stay there again!"
United States
Marisa H.
The price is HK$893
HK$1,723 total
includes taxes & fees
7 Nov - 8 Nov
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Interior
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
10.0 out of 10, Exceptional, (4)
"This place is a hidden gem! Would definitely host a gathering here again :)"
United States
Rachel S.
The price is HK$2,937
HK$3,357 total
includes taxes & fees
3 Nov - 4 Nov
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Greenville Home w/ Private Yard
Pet-Friendly Greenville Home w/ Private Yard
10.0 out of 10, Exceptional, (23)
"Another terrific stay! Its like a home away from home and very accommodating with the fenced in backyard and provided dog bags."
United States
Abraham S.
Pet-Friendly Greenville Home w/ Private Yard
Dining
Retro Home Close to Campus
Retro Home Close to Campus
9.8 out of 10, Exceptional, (6)
"We had a great stay! The location was perfect-close to everything we needed. The space was ideal for kids, with plenty of room to play and relax. Highly recommend for families looking for comfort and convenience."
United States
Sarah M.
The price is HK$1,049
HK$2,306 total
includes taxes & fees
2 Nov - 3 Nov
Retro Home Close to Campus
Interior
Boho Bungalow off Main-one block from Lovely Park
Boho Bungalow off Main-one block from Lovely Park
9.0 out of 10, Wonderful, (12)
"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."
United States
Kelly R.
The price is HK$738
HK$1,392 total
includes taxes & fees
3 Nov - 4 Nov
Boho Bungalow off Main-one block from Lovely Park
Fridge, microwave, oven, stovetop
3-bedroom vacation home 9 minutes from Ball State University in the country.
3-bedroom vacation home 9 minutes from Ball State University in the country.
8.6 out of 10, Excellent, (40)
"We enjoyed the house and the large yard. There was plenty of room for our family and while we were in town for an event, it allowed us time to relax in the evening and room to prepare for the next day. "
United States
William R.
3-bedroom vacation home 9 minutes from Ball State University in the country.
Terrace/patio
Charming Home! Prime Location! Dog-Friendly!
Charming Home! Prime Location! Dog-Friendly!
10.0 out of 10, Exceptional, (12)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is HK$1,224
HK$2,563 total
includes taxes & fees
10 Nov - 11 Nov
Charming Home! Prime Location! Dog-Friendly!
Interior
Cozy RV close to the Reservoir
Cozy RV close to the Reservoir
2.0 star property
6.0 out of 10, (1)
"This was a really neat idea, and the kids were very excited to stay in an RV. I will start by saying it was very clean. It was not advertised that this was on private property right next to the house until check in time. The location was also not optimal because it was right next to the main road where you could hear every car, and the entrance was across from what looked like a lot of junk. . we had to deal with a dog barking all night, long, but we made the best of all this. The only thing...
United States
Eleisha G.
The price is HK$804
HK$1,249 total
includes taxes & fees
2 Nov - 3 Nov
Cozy RV close to the Reservoir
Property grounds
Charming 3-bedroom house with AC, WiFi in Greenville
Charming 3-bedroom house with AC, WiFi in Greenville
9.0 out of 10, Wonderful, (6)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is HK$1,220
HK$1,927 total
includes taxes & fees
3 Nov - 4 Nov
Charming 3-bedroom house with AC, WiFi in Greenville
Dining
Top-Rated Guest Favorite- Near Ball State & IU Hospital • October Specials
Top-Rated Guest Favorite- Near Ball State & IU Hospital • October Specials
10.0 out of 10, Exceptional, (27)
"The house was clean, nicely remodeled and had everything we needed. It was also a great location and near everything we wanted to be. They had fun games, an awesome back yard and covered parking. Highly recommend!"
United States
Brandon H.
Top-Rated Guest Favorite- Near Ball State & IU Hospital • October Specials
Dining
5 min walk to BSU Campus - Quiet Neighborhood
5 min walk to BSU Campus - Quiet Neighborhood
10.0 out of 10, Exceptional, (72)
"A quiet neighborhood with a private back yard and we had everything we needed for a wonderful weekend celebrating a birthday and retirement. Would stay here again!"
United States
Tammy W.
5 min walk to BSU Campus - Quiet Neighborhood
Dining
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
10.0 out of 10, Exceptional, (23)
"Stayed multiple times, always great, the owners are amazing and helpful."
United States
Randy G.
The price is HK$971
HK$2,654 total
includes taxes & fees
6 Nov - 7 Nov
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Interior
THE STARR LOFT- Earlham, IUEast, Historic District
THE STARR LOFT- Earlham, IUEast, Historic District
9.4 out of 10, Exceptional, (35)
"Property is so unique and cozy. We really enjoyed the stay. So much better than a hotel. Location is great. Walkable to many restaurants. Would definitely recommend. "
United States
Renee M.
THE STARR LOFT- Earlham, IUEast, Historic District
Microwave, oven, stovetop, dishwasher
Brand new, spacious 3-bedroom apartment close to Ball State and IU Health.
Brand new, spacious 3-bedroom apartment close to Ball State and IU Health.
Brand new, spacious 3-bedroom apartment close to Ball State and IU Health.
Exterior
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
10.0 out of 10, Exceptional, (1)
"House is cute - loved all the wood floors although they're noisy. beds were comfortable. only stayed one night but it was walkable back and forth to campus so that was great"
United States
Abi Z.
The price is HK$1,088
HK$1,619 total
includes taxes & fees
9 Nov - 10 Nov
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Exterior
lake front 2 br condo close to bsu
lake front 2 br condo close to bsu
9.4 out of 10, Exceptional, (52)
"10/10"
United States
Andrew M.
lake front 2 br condo close to bsu
8 bedrooms, WiFi, bed sheets
Westcott Mansion with Pickleball Court & Huge Gazebo
Westcott Mansion with Pickleball Court & Huge Gazebo
9.8 out of 10, Exceptional, (34)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
United States
Jeff N.
The price is HK$1,282
HK$2,584 total
includes taxes & fees
5 Nov - 6 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo
Property grounds
Tiny Home at Camp Mahanaim - New Paris, OH - Private Lake
Tiny Home at Camp Mahanaim - New Paris, OH - Private Lake
10.0 out of 10, Exceptional, (2)
"Very peaceful and safe. Comfortable and well supplied."
United States
Laura B.
Tiny Home at Camp Mahanaim - New Paris, OH - Private Lake
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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Top Winchester Hotel Reviews

Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70

10/10 Excellent
"In 2025, the nearby construction is getting close to finished, but there were no noise or dust issues and the hotel was very nice and very clean. I’d stay there again any time."
Ken 1-night trip
Posted 3 days ago
Best Western Plus Richmond Indiana I-70

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its golf courses.

What are some of the best holiday rentals that Winchester has to offer?

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA: This highly rated holiday home rental in Winchester is located in a rural location, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

While you're exploring the area, Prairie Creek Reservoir and Campground and Burlington Lake are a couple of picturesque spots to get outside and enjoy nature. Winchester Golf Club and Winchester Speedway are other places to visit while you're in town.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family gatherings.