Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Fridge, microwave, oven, stovetop
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
10.0 out of 10, Exceptional, (159)
"Overall a perfect Bachelor Party for us 25 - 55 year old guys! Basketball, Firepit, cooking out, Pool and more! Highly recommend if you plan for a one stop place of bringing your food, booze, and fun!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Exterior
lake front 2 br condo close to bsu
9.2 out of 10, Wonderful, (24)
"Booked the condo for a 2 night weekend stay due to a volleyball tournament in yorktown. The place was like a mini vacation, the lake view was beautiful, the weather was perfect and I was able to grill some food in the patio and soak in the hot tub before bed. If my daughter has any more volleyball tournaments nearby I will 100% look for this listing first. The condo had all the necessities and the location was perfect. Volleyball is stressful and it was so nice to have this place to go to after...
lake front 2 br condo close to bsu
Property grounds
5 min walk to BSU Campus - Quiet Neighborhood
10.0 out of 10, Exceptional, (42)
"This house is perfect for any family or friends visiting BSU for any reason due to its location, cleanliness, ease of entry and ranch house layout. I wish we had discovered it our daughter's freshman year as we would have stayed here for every visit, show, or drop-off! Thank you!"
5 min walk to BSU Campus - Quiet Neighborhood
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Fridge, microwave, oven, stovetop
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
The price is €154
includes taxes & fees
14 May - 15 May
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Fridge, microwave, oven, stovetop
country home with hot tub close to town
9.0 out of 10, Wonderful, (26)
"The home was perfectly located for watching totality in 2024. Just far enough out of town to have a country feel, but close enough to Muncie to make shopping and dining convenient."
country home with hot tub close to town
Fridge, microwave, oven, stovetop
!Country Home Get Away! !Private Backyard!
10.0 out of 10, Exceptional, (7)
"Property is as described. Super quiet, perfect for a place to stay while in the area working."
!Country Home Get Away! !Private Backyard!
Outdoor dining
2 Bedroom Retreat near Earlham College in Richmond IN
10.0 out of 10, Exceptional, (18)
"After you park you enter a little Oasis right in town. This place is stunning! Beds and couches are comfortable! Listening to the tiny waterfall in this wonderful backyard setting is a must! Landscape is immaculate. You almost feel secluded like you are out in the woods, because of all the trees surrounding majority of the place. Best candle company(Warm Glow) shop 15 min drive."
2 Bedroom Retreat near Earlham College in Richmond IN
Exterior
Quaker Hill Cottage on gated estate with fire pit & hiking trails
9.8 out of 10, Exceptional, (10)
"This property is awesome! Beautiful home with everything you need. The owner was very easy to reach, responded immediately, and worked with us when we needed to make last minute changes. We totally enjoyed our stay and highly recommend this place :)"
The price is €211
includes taxes & fees
15 May - 16 May
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Exterior
Cardinal Cottage - 2 bedroom cozy home
10.0 out of 10, Exceptional, (1)
"Clean and comfortable two bedroom"
The price is €171
includes taxes & fees
14 May - 15 May
Cardinal Cottage - 2 bedroom cozy home
Fridge, microwave, oven, stovetop
3 br country home close to town with hot tub
9.6 out of 10, Exceptional, (13)
"Older home but very comfortable and super clean and well stocked. We will rent this house sgain."
3 br country home close to town with hot tub
Private kitchen
Boho Bungalow off Main-one block from Lovely Park
9.2 out of 10, Wonderful, (5)
"We liked the cleanliness of the property. There is also plenty of things to do and great places to eat with in a short distance of the property"
The price is €124
includes taxes & fees
14 May - 15 May
Boho Bungalow off Main-one block from Lovely Park
Property grounds
Charming Home Close to all Richmond has to Offer! Dog-Friendly
The price is €334
includes taxes & fees
16 May - 17 May
Charming Home Close to all Richmond has to Offer! Dog-Friendly
8 bedrooms, WiFi, bed sheets
Westcott Mansion with Pickleball Court & Huge Gazebo
9.8 out of 10, Exceptional, (18)
"It was a great place for our group to gather to watch the eclipse, and then visit with each other afterwards. Very historic house with potential to be even more grand if renovations continue. The gazebo is nice. The yard would be even better with a garden or flowering trees. We enjoyed exploring the house. So much room!"
The price is €291
includes taxes & fees
15 May - 16 May
Westcott Mansion with Pickleball Court & Huge Gazebo
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 €243
includes taxes & fees
14 May - 15 May
La Dolce Vita
Outdoor pool, a heated pool
Cozy Cabin with fireplace, hot tub & hiking trails
7.4 out of 10, Good, (3)
"The property is amazing. Pictures do not do the gardens justice. The visiting horse and friendly cats were a plus. The pool is cloudy and needs more frequent cleaning than the weekly service due to its location under trees. The outdoor furniture also needs cleaning as do the dishes in the house. But you will hardly notice because the gardens are so well maintained and the hot tub works amazing."
Cozy Cabin with fireplace, hot tub & hiking trails
Fridge, microwave, oven, stovetop
Newly renovated studio in Hagerstown--Self Check-in
10.0 out of 10, Exceptional, (22)
"It looks just like the pictures. Very clean. The parking was very convenient. I would absolutely stay here again."
The price is €151
includes taxes & fees
2 Jun - 3 Jun
Newly renovated studio in Hagerstown--Self Check-in
Fridge, microwave, stovetop, dishwasher
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
10.0 out of 10, Exceptional, (8)
"Quiet, clean and comfy!"
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
Exterior
Recently remodeled Colonial-style home with room for the whole family!
10.0 out of 10, Exceptional, (18)
"Family and friends enjoyed our short visit. Quiet and secluded back yard with comfortable seating and a fire pit"
Recently remodeled Colonial-style home with room for the whole family!
Fridge, microwave, oven, stovetop
Elegant House 2 min from BSU/Hospital/Downtown
10.0 out of 10, Exceptional, (1)
"Lovely, well equipped, two story house in calm area near BSU; host was very responsive to minor glitch in door lock; property and house were very nicely decorated and maintained; kitchen was well equipped; linens were fresh; even a Brita pitcher was available to help with Muncie's known water "flavor" Highly recommend property to all unless steep stairs to bedrooms would pose an issue."
The price is €398
includes taxes & fees
14 May - 15 May
Elegant House 2 min from BSU/Hospital/Downtown
Living area
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
10.0 out of 10, Exceptional, (10)
"Fishing was amazing and lots of space for our kids to run and play!"
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
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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.

Other types of properties in Winchester you may be interested in

Golf
Randolph Inn and Suites
2.5 star property
9.0 out of 10, Wonderful, (183)
"Super friendly and clean!!!"
The price is €156
includes taxes & fees
14 May - 15 May
Randolph Inn and Suites
Pillow-top beds, desk, blackout curtains, iron/ironing board
Baymont by Wyndham Muncie Near Ball State University
2.5 star property
5.8 out of 10, (1007)
"Clean"
The price is €69
includes taxes & fees
20 May - 21 May
Baymont by Wyndham Muncie Near Ball State University
Lobby
Baymont by Wyndham Richmond I-70
2.5 star property
8.0 out of 10, Very good, (888)
"."
The price is €70
includes taxes & fees
19 May - 20 May
Baymont by Wyndham Richmond I-70
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.

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?

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 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 garden, a pool table and 1 hot tub 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 Summit Lake State Park are a couple of picturesque spots to get outside and enjoy nature. Winchester Speedway and Historic Shopping & Dining District of Winchester, Indiana 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.