Winchester Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Winchester holiday rentals

Fridge, microwave, oven, stovetop

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 reviews)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
The price is HK$891
HK$1,768 total
includes taxes & fees
17 Feb - 18 Feb
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
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+
Hagerstown
10.0 out of 10, Exceptional, (12 reviews)
"Very conveniently located with clear instructions about amenities. We will stay here again sometime."
United States
MaryandMichael P.
The price is HK$556
HK$1,279 total
includes taxes & fees
9 Feb - 10 Feb
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
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
Muncie
10.0 out of 10, Exceptional, (7 reviews)
"The place was super clean, the bed was really comfortable, and the bathroom was big and well-maintained. The host gave me the necessary info before I needed to ask for it which is not always the case. It is located really close to Ball State. If my daughter chooses to go to school there we will be staying here for sure!"
United States
Julie H.
The price is HK$626
HK$1,270 total
includes taxes & fees
21 Feb - 22 Feb
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Fridge, microwave, oven, stovetop

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.2 out of 10, Wonderful, (21 reviews)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is HK$457
HK$1,081 total
includes taxes & fees
9 Feb - 10 Feb
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Interior

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (35 reviews)
"Very clean and easy weekend stay"
United States
Ally B.
The price is HK$703
HK$1,313 total
includes taxes & fees
21 Feb - 22 Feb
Cardinal Cottage - 2 bedroom cozy home
Living area

Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.2 out of 10, Wonderful, (15 reviews)
"Lovely house, easy check-in, great location."
United States
Heather S.
The price is HK$742
HK$1,400 total
includes taxes & fees
2 Mar - 3 Mar
Boho Bungalow off Main-one block from Lovely Park
Fridge, microwave, oven, stovetop

3 Bedroom House in Fort Recovery

3 Bedroom House in Fort Recovery
Fort Recovery
10.0 out of 10, Exceptional, (23 reviews)
"Great!"
United States
Neil D.
The price is HK$1,055
HK$2,133 total
includes taxes & fees
9 Feb - 10 Feb
3 Bedroom House in Fort Recovery
Interior

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$953
HK$2,621 total
includes taxes & fees
9 Feb - 10 Feb
2BR Updated Dtwn Condo: Streaming, Patio, W & D
TV

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

2BR Updated Dtwn Condo: Streaming, Patio, W & D
Muncie
10.0 out of 10, Exceptional, (18 reviews)
"Great apartment with everything needed for a restful stay!"
United States
David G.
The price is HK$859
HK$2,698 total
includes taxes & fees
9 Feb - 10 Feb
2BR Updated Dtwn Condo: Streaming, Patio, W & D
Dining

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (10 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is HK$1,055
HK$2,319 total
includes taxes & fees
9 Feb - 10 Feb
Retro Home Close to 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.
Greenville
9.2 out of 10, Wonderful, (11 reviews)
"House was perfect for our family to stay for our daughter's wedding "
United States
Molly L.
The price is HK$1,210
HK$1,913 total
includes taxes & fees
9 Feb - 10 Feb
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!
Richmond
9.8 out of 10, Exceptional, (13 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is HK$1,231
HK$2,577 total
includes taxes & fees
9 Feb - 10 Feb
Charming Home! Prime Location! Dog-Friendly!
Interior

Cozy RV close to the Reservoir

Cozy RV close to the Reservoir
Selma
6.0 out of 10, (1 review)
"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$809
HK$1,256 total
includes taxes & fees
9 Feb - 10 Feb
Cozy RV close to the Reservoir
Exterior

Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville
Greenville
9.2 out of 10, Wonderful, (9 reviews)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is HK$1,227
HK$1,930 total
includes taxes & fees
9 Feb - 10 Feb
Charming 3-bedroom house with AC, WiFi in Greenville
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
Muncie
The price is HK$752
HK$1,674 total
includes taxes & fees
9 Feb - 10 Feb
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
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
Muncie
10.0 out of 10, Exceptional, (1 review)
"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$1,125
HK$1,654 total
includes taxes & fees
10 Feb - 11 Feb
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Interior

Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (35 reviews)
"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$1,289
HK$2,512 total
includes taxes & fees
12 Feb - 13 Feb
Westcott Mansion with Pickleball Court & Huge Gazebo
Interior

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, (9 reviews)
"Not only was the property amazing an as advertised but the Host was incredibly nice and accommodating would highly recommend."
United States
Mike S.
The price is HK$2,461
HK$2,813 total
includes taxes & fees
9 Feb - 10 Feb
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Exterior

Country living 4 Bedroom House

Country living 4 Bedroom House
Delaware Township
The price is HK$7,032
HK$8,856 total
includes taxes & fees
9 Feb - 10 Feb
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

Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond

10/10 Excellent
"Loved the room, spacious, clean, close to shopping and restaurants. "
Karen 3-night trip
Posted 5 days ago
Home2 Suites by Hilton Richmond

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:

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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?

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.