Winchester Holiday Rentals

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Winchester holiday rentals

Fridge, microwave, oven, stovetop
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

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

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Hagerstown
10.0 out of 10, Exceptional, (11)
"Very conveniently located with clear instructions about amenities. We will stay here again sometime."
United States
MaryandMichael P.
The price is HK$553
HK$1,273 total
includes taxes & fees
22 Dec - 23 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Interior
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Fort Recovery
10.0 out of 10, Exceptional, (7)
"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!!"
United States
Tony & Cindy M.
The price is HK$2,941
HK$3,361 total
includes taxes & fees
21 Dec - 22 Dec
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Interior
Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (29)
"Very clean and easy weekend stay"
United States
Ally B.
The price is HK$700
HK$1,307 total
includes taxes & fees
21 Dec - 22 Dec
Cardinal Cottage - 2 bedroom cozy home
Interior
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

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

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Muncie
10.0 out of 10, Exceptional, (6)
"Excellent hospitality and accommodations!It was so nice to have snacks available waiting for us upon arrival. The ice and water options were so nice. We felt so at home in this safe, quiet neighborhood with discreet parking right at the door. Hope to book again when we come to visit our family. Easy access with personalized code provided from owner. Clean, great communication, had everything we needed.Thank you so much."
United States
Tamara B.
The price is HK$693
HK$1,342 total
includes taxes & fees
21 Dec - 22 Dec
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Fridge, microwave, oven, stovetop
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Muncie
10.0 out of 10, Exceptional, (4)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
The price is HK$719
HK$1,415 total
includes taxes & fees
8 Jan - 9 Jan 2026
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Fridge, microwave, oven, stovetop
New Hagerstown Apartment - Self Check-in. Sleeps 4+

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.2 out of 10, Wonderful, (20)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is HK$521
HK$1,150 total
includes taxes & fees
5 Jan - 6 Jan 2026
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Interior
2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D
2.5 star property
Muncie
The price is HK$949
HK$2,610 total
includes taxes & fees
21 Dec - 22 Dec
2BR Updated Dtwn Condo: Streaming, Patio, W & D
Dining
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus

Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus

Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Muncie
10.0 out of 10, Exceptional, (1)
"House is cute - loved all the wood floors although they're noisy. beds were comfortable. only stayed one night but it was walkable back and forth to campus so that was great"
United States
Abi Z.
The price is HK$1,120
HK$1,647 total
includes taxes & fees
4 Jan - 5 Jan 2026
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Smart TV, table football
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

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

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
2.0 star property
Greenville
9.2 out of 10, Wonderful, (9)
"Comfy and clean!"
United States
rey v.
The price is HK$1,204
HK$1,913 total
includes taxes & fees
24 Dec - 25 Dec
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Exterior
Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (13)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is HK$1,225
HK$2,567 total
includes taxes & fees
22 Dec - 23 Dec
Charming Home! Prime Location! Dog-Friendly!
Interior
Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (35)
"We had the best time. House was gorgeous and unique. Perfect place for our group as everyone had their own room and their own bed! Would absolutely stay here again. "
United States
Megan H.
The price is HK$1,284
HK$2,588 total
includes taxes & fees
25 Dec - 26 Dec
Westcott Mansion with Pickleball Court & Huge Gazebo
Interior
Cozy RV close to the Reservoir

Cozy RV close to the Reservoir

Cozy RV close to the Reservoir
2.0 star property
Selma
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...
United States
Eleisha G.
The price is HK$805
HK$1,251 total
includes taxes & fees
21 Dec - 22 Dec
Cozy RV close to the Reservoir
Dining
Modern meets Victorian house in the fantastic Historic District of Richmond.

Modern meets Victorian house in the fantastic Historic District of Richmond.

Modern meets Victorian house in the fantastic Historic District of Richmond.
2.0 star property
Richmond
The price is HK$1,401
HK$2,963 total
includes taxes & fees
21 Dec - 22 Dec
Modern meets Victorian house in the fantastic Historic District of Richmond.
Living area
Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.0 out of 10, Wonderful, (14)
"Lovely house, easy check-in, great location."
United States
Heather S.
The price is HK$739
HK$1,394 total
includes taxes & fees
23 Dec - 24 Dec
Boho Bungalow off Main-one block from Lovely Park
TV
2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D
2.0 star property
Muncie
The price is HK$778
HK$2,389 total
includes taxes & fees
21 Dec - 22 Dec
2BR Updated Dtwn Condo: Streaming, Patio, W & D
Exterior
Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville
Greenville
9.0 out of 10, Wonderful, (8)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is HK$1,222
HK$1,930 total
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-bedroom house with AC, WiFi in Greenville
Dining
Retro Home Close to Campus

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (10)
"Nice property no hassel stay!"
United States
Donald D.
The price is HK$1,050
HK$2,309 total
includes taxes & fees
22 Dec - 23 Dec
Retro Home Close to Campus
2 bedrooms, WiFi, bed sheets
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State

Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State

Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
Muncie
The price is HK$616
HK$1,518 total
includes taxes & fees
23 Dec - 24 Dec
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
Exterior
Country living 4 Bedroom House

Country living 4 Bedroom House

Country living 4 Bedroom House
Delaware Township
The price is HK$7,003
HK$8,854 total
includes taxes & fees
21 Dec - 22 Dec
Country living 4 Bedroom House
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

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

10/10 Excellent
"This was a beautiful home was enjoyed by all. The amenities are great, Walmart is right around the corner, the pool was warm and Ted was very welcoming. We were disappointed to learn that the hot tub had been closed early due to cold weather, but that don’t stop us from having a great time! We would definitely recommend this place to anyone interested in renting their own “hotel” for a family/friend getaway!"
Kaylee M. 2-night trip
Posted 4 days ago
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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?

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA: 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.

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.