Winchester Holiday Rentals

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Holiday Rentals in Winchester

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

10.0 out of 10, Exceptional, (181)
"Our family tries to get together at least once each year, normally around the Christmas holiday. We (2 grandparents, 8 children and spouses, and 15 grandchildren ages 7 to 30) came to this Ft Recovery gem from Ohio, Illinois, New York, Los Angeles and Virginia. The main floor open kitchen, living room and eating spaces, game area in the lower floor, and fantastic adjacent building with full basketball/volleyball court and loft with wet bar allowed us to spread out and spend time in small groups...
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

Quaker Hill Cottage on gated estate with fire pit & hiking trails

9.8 out of 10, Exceptional, (21)
"Such an interesting place. It was a great stay. We would definitely stay there again!"
The price is AU$351
includes taxes & fees
9 Mar - 10 Mar
Quaker Hill Cottage on gated estate with fire pit & hiking trails

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

9.8 out of 10, Exceptional, (7)
"The house was just as describedThe host was great and quickly responded with when i had questions. We arrived to find a nice note and home baked cookies. The berries was great and it was very spacious for our large group. Definitely recommend"
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

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

10.0 out of 10, Exceptional, (7)
"Ck in had some snags due to equipment bugs. However once in contact with host it was handled quickly and very professionally. We enjoyed this rental and will stay here again when visiting family. Michelle is a superhost and very congenial. "
The price is AU$260
includes taxes & fees
10 Feb - 11 Feb
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Quaint Economy Retreat w/ Patio & Spacious Yard!

9.4 out of 10, Exceptional, (6)
"This property is maintained very well and is clean. Three people stayed and there was more than enough room. The owners were very responsive and accommodating. We would recommend this property and owner. "
Quaint Economy Retreat w/ Patio & Spacious Yard!

Westcott Mansion with Pickleball Court & Huge Gazebo

9.8 out of 10, Exceptional, (28)
"We stayed for the weekend at the Westport mansion to celebrate two of our sisters’ big milestone birthdays. The five of us each had our own rooms in this beautiful home. It is surprisingly quiet given the house is just a block off a busy road. The neighborhood was quiet and we were just minutes from pretty much everything in town. The place is so big, with so many beautiful sitting rooms that we joked we should set a timer and move to a different place to hang out every 30 minutes. Some times at...
The price is AU$535
includes taxes & fees
9 Mar - 10 Mar
Westcott Mansion with Pickleball Court & Huge Gazebo

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (37)
"If mattresses are replaced, rating would be Excellent!"
lake front 2 br condo close to bsu

Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir

9.6 out of 10, Exceptional, (14)
"Really nice place perfect for 6 people"
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir

The University House King Beds+Fast WIFI+W/D

10.0 out of 10, Exceptional, (3)
"Great place, very clean and very nice house. Worked well for a large number of people. "
The University House King Beds+Fast WIFI+W/D

Cozy Home! ✶ 2 Bedroom house ✶ Close to IU Health Hospital & Collage

10.0 out of 10, Exceptional, (14)
"We traveled to Muncie for a family wedding and were so happy to have found Kyle and Shannah’s place. It was clean, in a quiet neighborhood, and close to Ball State. The hosts were quick and easy to communicate with! We would happily stay there again."
Cozy Home! ✶ 2 Bedroom house ✶ Close to IU Health Hospital & Collage

THE STARR LOFT- Earlham, IUEast, Historic District

9.2 out of 10, Wonderful, (20)
"This was a great place to stay. We were in town for a concert in indy and everything in indy was a fortune. We found this place a little outside of indy but not too far. The place is amazing and beautiful. The decor fits it real.well the exposed rafters i love. Its kind of a vintage feel. I told my daughter when we got there i loved the place so much im not leaving. She told me i have to because she plans on not leaving. Plenty of food and dining just a mile or two away. I dont know if ill...
THE STARR LOFT- Earlham, IUEast, Historic District

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

10.0 out of 10, Exceptional, (31)
"We really enjoyed our stay here, what a lovely home. "
Recently remodeled Colonial-style home with room for the whole family!

2 Bedroom Retreat near Earlham College in Richmond IN

10.0 out of 10, Exceptional, (25)
"We loved the home along with all of the amenities. If your contemplating on which house to stay in choose this one! Cindy provided so many extras! From blankets, towels, kitchen dishes to seasonings & even the basic “staples” in the refrigerator along w snacks. Very beautiful home with character . Thankyou opening your home up to us . We will return! "
2 Bedroom Retreat near Earlham College in Richmond IN

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

7.0 out of 10, Good, (4)
"Wasn't sure about the neighborhood at first but we had zero issues. House is a bit dated and the front bedroom smelled of smoke. When we arrived there were no towels or washcloths and the bathroom sink was very slow to drain. Messaged the property owner and everything was taken care of within an hour!! EXCELLENT customer service! Overall not a bad experience and it was very convenient to my activity."
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

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 AU$288
includes taxes & fees
20 Feb - 21 Feb
Boho Bungalow off Main-one block from Lovely Park

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!

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

9.6 out of 10, Exceptional, (14)
"What a cute little apartment that fit my needs of my trip. The whole place was so clean and updated. Bed was so comfortable. Was so relaxing late evenings with fireplace on watching a movie with a glass of wine. My brother’s girlfriend commented how nice and wide the steps were up to the quaint little patio. Getting I was a breeze. The host was very accommodating and checking to make sure I had everything I needed. The only negative thing I could say was bed pillow was too hard for me but I...
The price is AU$217
includes taxes & fees
13 Feb - 14 Feb
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"The apartment was cute and clean. We had no problems whatsoever!!"
The price is AU$208
includes taxes & fees
9 Feb - 10 Feb
Newly renovated studio in Hagerstown--Self Check-in

Godstow House, Come and stay awhile!

Godstow House, Come and stay awhile!

Cardinal Cottage - 2 bedroom cozy home

9.4 out of 10, Exceptional, (9)
"Cutest cottage and fabulous hosts went above and beyond for us! Thank you Cole and Margee!"
The price is AU$288
includes taxes & fees
10 Feb - 11 Feb
Cardinal Cottage - 2 bedroom cozy home
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 types of properties in Winchester you may be interested in

Randolph Inn and Suites

2.5 star property
9.0 out of 10, Wonderful, (211)
"Very nice "
The price is AU$178
includes taxes & fees
8 Feb - 9 Feb
Randolph Inn and Suites

Baymont by Wyndham Richmond I-70

2.5 star property
8.0 out of 10, Very good, (1002)
"I have never stayed at a hotel that is all around friendly and helpful. From check-in, key return, and host in the dining room."
The price is AU$116
includes taxes & fees
9 Feb - 10 Feb
Baymont by Wyndham Richmond I-70

Comfort Suites

2.5 star property
9.4 out of 10, Exceptional, (424)
"This was one of the cleanest hotels I’ve ever stayed in. The rooms were large and the beds were extremely comfortable. I will stay there again if I’m in that area. "
The price is AU$176
includes taxes & fees
9 Mar - 10 Mar
Comfort Suites
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 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.