Winchester Holiday Rentals

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Check prices for these dates

Tonight
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Holiday Rentals in Winchester

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Enjoy a meal under the stars at this serene outdoor dining area, complete with a picnic table and twinkling string lights.

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
Enjoy a game of basketball in our indoor court with two hoops and a high ceiling featuring a geometric pattern.

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.
Relax in this spacious living area with a large window offering a view of the outdoors, a comfortable sofa, and a kitchen with a bar area.

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
Relax in a charming room with a comfortable seating area, sofa, and round table, featuring a large chandelier and large windows.

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!
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and dishwasher.

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
Relax in this stylish living room with a comfortable sofa, desk, and flat-screen TV.

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!
Traditional home with a charming front porch and well-manicured yard.

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
Enjoy meals in this dining area with a round table and six chairs.

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
Enjoy cooking in this kitchen with a refrigerator, sink, and table.

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

10.0 out of 10, Exceptional, (20)
"Stayed for 6 nights. Every thing was super clean. Communication with host was wonderful. I will totally be disappointed at my next stay in Muncie if I’m unable to book this listing. A great place to stay*****"
Summer Specials-Guest favorite! Near IU Hospital & Ball State University
Cozy RV close to the Reservoir
Cozy seating area with leather couch and small table, perfect for relaxing.

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 HK$812
HK$1,262 total
includes taxes & fees
1 Aug - 2 Aug
Cozy RV close to the Reservoir
Boho Bungalow off Main-one block from Lovely Park
Compact kitchen with a refrigerator, stove, and shelving for kitchen essentials.

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 HK$1,068
HK$1,794 total
includes taxes & fees
28 Jul - 29 Jul
Boho Bungalow off Main-one block from Lovely Park
Charming Home! Prime Location! Dog-Friendly!
Relax in a serene outdoor setting with a fire pit and Adirondack chairs amidst a peaceful wooded environment.

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 HK$1,374
HK$2,769 total
includes taxes & fees
22 Aug - 23 Aug
Charming Home! Prime Location! Dog-Friendly!
Cardinal Cottage - 2 bedroom cozy home
Welcome to this charming single-story home with a cozy front porch and inviting garden.

Cardinal Cottage - 2 bedroom cozy home

9.8 out of 10, Exceptional, (18)
"The property is furnished to a high standard."
The price is HK$706
HK$1,319 total
includes taxes & fees
29 Jul - 30 Jul
Cardinal Cottage - 2 bedroom cozy home
Charming 3-bedroom house with AC, WiFi in Greenville
Stroll through the beautifully manicured lawn to a charming shed surrounded by lush trees.

Charming 3-bedroom house with AC, WiFi in Greenville

The price is HK$1,232
HK$1,947 total
includes taxes & fees
31 Jul - 1 Aug
Charming 3-bedroom house with AC, WiFi in Greenville
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Stunning home with a lush lawn and mature tree, offering a peaceful retreat.

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 HK$1,215
HK$1,929 total
includes taxes & fees
28 Jul - 29 Jul
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
Meetings take place around a large table in this well-lit 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 HK$1,091
HK$2,842 total
includes taxes & fees
31 Jul - 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+
Cozy living space with a kitchen and living area, featuring a sofa, armchair, and oven.

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 HK$558
HK$1,285 total
includes taxes & fees
28 Jul - 29 Jul
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Enjoy a bright and airy living space with a kitchen and living area, featuring a sofa, coffee table, and rug.

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 HK$459
HK$1,086 total
includes taxes & fees
5 Aug - 6 Aug
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Retro Home Close to Campus
Enjoy meals in style with a table set for four, featuring a geometric pattern and comfortable black chairs.

Retro Home Close to Campus

9.6 out of 10, Exceptional, (5)
The price is HK$1,060
HK$2,339 total
includes taxes & fees
27 Jul - 28 Jul
Retro Home Close to Campus
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Enjoy cooking in the fully equipped kitchen with stainless steel appliances and white cabinetry.

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

The price is HK$629
HK$1,276 total
includes taxes & fees
30 Jul - 31 Jul
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

Comfort Suites

Comfort Suites

10/10 Excellent
"Our stay was excellent. Check in was simple, the room was spacious and clean, and everything was very modern. The bed was comfortable and we slept great!! I wish we could have spent more than one night there."
Dana 1-night trip
Posted 1 day ago
Comfort Suites

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.