Winchester Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Winchester holiday rentals

Interior

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is HK$672
HK$2,575 total
includes taxes & fees
28 Mar - 29 Mar
Pets Welcome! Quiet Economy Home w/ Spacious Yard
TV

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
The price is HK$602
HK$2,577 total
includes taxes & fees
28 Mar - 29 Mar
Pets Welcome! Quiet Economy Home w/ Spacious Yard
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, (22 reviews)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is HK$458
HK$1,083 total
includes taxes & fees
30 Mar - 31 Mar
New Hagerstown Apartment - Self Check-in. Sleeps 4+
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, (13 reviews)
"Very conveniently located with clear instructions about amenities. We will stay here again sometime."
United States
MaryandMichael P.
The price is HK$557
HK$1,281 total
includes taxes & fees
29 Mar - 30 Mar
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
TV

'Downtown Delight' w/ Patio! 1 Mi to Ball State

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
10.0 out of 10, Exceptional, (20 reviews)
"Great host and all the amenities were in great condition."
United States
Dan H.
The price is HK$860
HK$2,691 total
includes taxes & fees
29 Mar - 30 Mar
'Downtown Delight' w/ Patio! 1 Mi to Ball State
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$1,009
HK$1,874 total
includes taxes & fees
14 Apr - 15 Apr
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
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)
"This was a great place to stay for our visit back to our hometown for a special celebration. Very convenient right there in this Beautiful little town. Renee went out of her way to accommodate us three friends who hadn’t seen each other for many years! Altho we weren’t there long this place is definitely a keeper for future trips!Once again….Thx for your hospitality Renee!"
United States
Linda W.
3 Bedroom House in Fort Recovery
Interior

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (36 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is HK$704
HK$1,313 total
includes taxes & fees
29 Mar - 30 Mar
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$743
HK$1,401 total
includes taxes & fees
28 Mar - 29 Mar
Boho Bungalow off Main-one block from Lovely Park
Smart TV, books

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

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.6 out of 10, Exceptional, (30 reviews)
"Very easy to find and such a charming home! Very quiet and beautiful area. "
United States
Angie P.
The price is HK$899
HK$1,707 total
includes taxes & fees
14 Apr - 15 Apr
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Interior

3 King Beds and one Twin size bed Entire Home Near Ball State & Hospital

3 King Beds and one Twin size bed Entire Home Near Ball State & Hospital
Muncie
The price is HK$865
HK$1,363 total
includes taxes & fees
1 Apr - 2 Apr
3 King Beds and one Twin size bed Entire Home Near Ball State & Hospital
Dining

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (11 reviews)
"Clean house, good location, fair price for the size. Would definitely stay again!"
United States
Anthony C.
The price is HK$1,055
HK$2,312 total
includes taxes & fees
27 Mar - 28 Mar
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, (12 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$1,922 total
includes taxes & fees
31 Mar - 1 Apr
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
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$1,939 total
includes taxes & fees
27 Mar - 28 Mar
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$697
HK$1,612 total
includes taxes & fees
29 Mar - 30 Mar
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
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, (10 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$2,955
HK$3,377 total
includes taxes & fees
30 Mar - 31 Mar
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
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$1,290
HK$2,601 total
includes taxes & fees
8 Apr - 9 Apr
Westcott Mansion with Pickleball Court & Huge Gazebo
Exterior

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (13 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
The price is HK$1,231
HK$2,579 total
includes taxes & fees
29 Mar - 30 Mar
Charming Home! Prime Location! Dog-Friendly!
Interior

'downtown Delight' w/ Patio! 1 Mi to Ball State

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
The price is HK$954
HK$2,622 total
includes taxes & fees
1 Apr - 2 Apr
'downtown Delight' w/ Patio! 1 Mi to Ball State
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
"Convenient off of highway, close to restaurants, staff friendly and polite"
Josie 1-night trip
Posted 16 hours 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:

  • View our selection of featured holiday rentals in Winchester
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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 Speedway and Winchester Golf Club 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.