Winchester Holiday Rentals

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Holiday Rentals in Winchester

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

9.8 out of 10, Exceptional, (189)
"Plenty of room for our 25 that stayed. The pool is wonderful. Very clean and communication is excellent. This was our second stay and will do it again. Thank you Ted"
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

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

10.0 out of 10, Exceptional, (194)
"This was so relaxing! Way better than the old bar hopping. Very nice and clean."
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

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

9.8 out of 10, Exceptional, (9)
"The atmosphere and views are stunning. The home is spacious for families. We enjoyed our stay. "
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (28)
"I wasn't expecting that a visit to my small hometown would end up being the nicest vacation stay I've had but it was. Walking distance to some fun restaurants and a great record store. Property itself was beautiful and well maintained in a renovated loft space. Lots of charm and attention to detail. This place makes me want to find reasons to visit Richmond more often!"
THE STARR LOFT- Earlham, IUEast, Historic District

Quaint Economy Retreat w/ Patio & Spacious Yard!

9.6 out of 10, Exceptional, (8)
"It was a great place out away from town but close enough you can make it into Richmond with a 15-20 min easy drive "
Quaint Economy Retreat w/ Patio & Spacious Yard!

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

7.8 out of 10, Good, (7)
"Good"
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

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

10.0 out of 10, Exceptional, (37)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
Recently remodeled Colonial-style home with room for the whole family!

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (67)
"Nice house close to Ball State and other activities. Great communication by the host and easy access into the house. Highly recommend. "
5 min walk to BSU Campus - Quiet Neighborhood

Summer Specials-Guest favorite! Near IU Hospital & Ball State University

10.0 out of 10, Exceptional, (20)
"The house is very clean and comfortably furnished. Hosts were attentive and responsive. I hope to stay there again."
Summer Specials-Guest favorite! Near IU Hospital & Ball State University

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...
The price is AU$247
includes taxes & fees
27 July - 28 July
Cozy RV close to the Reservoir

Boho Bungalow off Main-one block from Lovely Park

9.4 out of 10, Exceptional, (8)
"Neighborhood a little blighted. Little house is a great piece of history. Very well maintained, appointed and loved. We were comfortable."
The price is AU$350
includes taxes & fees
28 July - 29 July
Boho Bungalow off Main-one block from Lovely Park

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (8)
"My husband, daughter and her 3 boys and dog were traveling home from vacation in New York and stayed here overnight. Everything was so comfortable and easy. I would definitely recommend this beautiful home away from home."
The price is AU$541
includes taxes & fees
11 Aug - 12 Aug
Charming Home! Prime Location! Dog-Friendly!

Cardinal Cottage - 2 bedroom cozy home

9.8 out of 10, Exceptional, (18)
"The property is furnished to a high standard."
The price is AU$258
includes taxes & fees
3 Aug - 4 Aug
Cardinal Cottage - 2 bedroom cozy home

Charming 3-bedroom house with AC, WiFi in Greenville

The price is AU$381
includes taxes & fees
5 Aug - 6 Aug
Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

2.0 star property
7.4 out of 10, Good, (3)
"This is a beautiful home with exceptional amenities. Is just about the closest home to the fairgrounds. Does need a gas grill.Thank you for letting us stay!!"
The price is AU$378
includes taxes & fees
28 July - 29 July
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Updated condo in the heart of Historic District with patio, streaming, fast WiFi

10.0 out of 10, Exceptional, (18)
"Great location. Safe . Easy check in and out process"
The price is AU$555
includes taxes & fees
31 July - 1 Aug
Updated condo in the heart of Historic District with patio, streaming, fast WiFi

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

9.8 out of 10, Exceptional, (8)
"Very clean and great amenities. Will be booking there again in the future."
The price is AU$251
includes taxes & fees
28 July - 29 July
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

New Hagerstown Apartment - Self Check-in. Sleeps 4+

9.6 out of 10, Exceptional, (15)
"Always a pleasure and the location is perfect for seeing family!"
The price is AU$213
includes taxes & fees
29 July - 30 July
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Retro Home Close to Campus

9.6 out of 10, Exceptional, (5)
The price is AU$457
includes taxes & fees
27 July - 28 July
Retro Home Close to Campus

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

The price is AU$252
includes taxes & fees
27 July - 28 July
The Cardinal. Newly built 1-bedroom cottage w/ 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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Top Winchester Hotel Reviews

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?

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!: 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.

How many holiday rentals are there in Winchester?

Expedia has 3 holiday rentals for your stay in Winchester.

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.