Holiday Rentals in Winchester

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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, (187)
"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, (191)
"An awesome place to stay with a large group. The indoor pickleball was a huge hit!!"
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.

Quaint Economy Retreat w/ Patio & Spacious Yard!

9.6 out of 10, Exceptional, (7)
"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

7.4 out of 10, Good, (6)
"Good"
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

Cardinal Cottage - 2 bedroom cozy home

9.6 out of 10, Exceptional, (15)
"Cutest cottage and fabulous hosts went above and beyond for us! Thank you Cole and Margee!"
The price is €147
includes taxes & fees
6 Jul - 7 Jul
Cardinal Cottage - 2 bedroom cozy home

The Red House

9.6 out of 10, Exceptional, (18)
"This was our 2nd stay at the red house while in town to visit family. Perfect location and space for our family of four. Friendly communication with the owner. Would happily stay again. Recommend!"
The price is €199
includes taxes & fees
6 Jul - 7 Jul
The Red House

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (64)
"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

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (25)
"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

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

10.0 out of 10, Exceptional, (19)
"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

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"Cute place. Property manager very responsive to needs. Great stay."
The price is €118
includes taxes & fees
15 Jul - 16 Jul
Newly renovated studio in Hagerstown--Self Check-in

Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10

10.0 out of 10, Exceptional, (1)
"We had an AMAZING time at Elm & Ivy!! What a beautiful venue for a chill bachelorette party!! There were so many perfect little touches that added to our stay. Highly recommend- we already talked about coming back again!!"
The price is €351
includes taxes & fees
2 Jul - 3 Jul
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10

Charming 3-bedroom house with AC, WiFi in Greenville

The price is €218
includes taxes & fees
21 Jul - 22 Jul
Charming 3-bedroom house with AC, WiFi in Greenville

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

10.0 out of 10, Exceptional, (36)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
Recently remodeled Colonial-style home with room for the whole family!

Westcott Mansion with Pickleball Court & Huge Gazebo

10.0 out of 10, Exceptional, (31)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
The price is €291
includes taxes & fees
14 Jul - 15 Jul
Westcott Mansion with Pickleball Court & Huge Gazebo

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

2.0 star property
6.0 out of 10, (2)
"Didn’t get in the house"
The price is €216
includes taxes & fees
14 Jul - 15 Jul
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (46)
"Very nice condo. Very clean which is very important to me. Was decorated with a Christmas tree for our December visit! Very close to anything you need."
lake front 2 br condo close to bsu

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (8)
"We are from Richmond originally and come back to visit family often. Definitely will be back. Great stay, great host, very accommodating, and clean. Highly recommend if you are in the area. "
The price is €289
includes taxes & fees
13 Jul - 14 Jul
Charming Home! Prime Location! Dog-Friendly!

Retro Home Close to Campus

10.0 out of 10, Exceptional, (2)
"Cute home, a lot of unique features. Great location. Owner was very easy to work with and accommodating to our group. Would totally rent this again ."
The price is €263
includes taxes & fees
1 Jul - 2 Jul
Retro Home Close to Campus

Boho Bungalow off Main-one block from Lovely Park

9.2 out of 10, Wonderful, (7)
"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 €159
includes taxes & fees
1 Jul - 2 Jul
Boho Bungalow off Main-one block from Lovely Park
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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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 YOLO 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.