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Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (27 reviews)
"The apartment was even better than expected!!! It was very clean and even had supplies provided such as toiletries and laundry detergent. It met my expectations and beyond!"
United States
Mindy
The price is NZ$257
includes taxes & fees
30 June - 1 July
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (40 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is NZ$312
includes taxes & fees
12 July - 13 July
Cardinal Cottage - 2 bedroom cozy home

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is NZ$575
includes taxes & fees
29 June - 30 June
Pets Welcome! Quiet Economy Home w/ Spacious Yard

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, (14 reviews)
"We had a great time and this place has everything that you need!"
United States
kirk h.
The price is NZ$285
includes taxes & fees
29 June - 30 June
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

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, (6 reviews)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (12 reviews)
"House was clean and close to all the things we needed to do. Beds very comfortable. Good location for us."
United States
Evelyn B.
The price is NZ$517
includes taxes & fees
23 June - 24 June
Retro Home Close to Campus

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
Muncie
The price is NZ$358
includes taxes & fees
23 June - 24 June
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

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, (31 reviews)
The price is NZ$381
includes taxes & fees
1 July - 2 July
Quaker Hill Cottage on gated estate with fire pit & hiking trails

'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, (25 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is NZ$590
includes taxes & fees
25 June - 26 June
'Downtown Delight' w/ Patio! 1 Mi to Ball State

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
The price is NZ$574
includes taxes & fees
29 June - 30 June
Pets Welcome! Quiet Economy Home w/ Spacious Yard

Benny B Charming 2 Bedroom house bunk/game room close to Ball State University

Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
Muncie
9.0 out of 10, Wonderful, (2 reviews)
"Such a cute little stay! Super easy and clear access to parking and the access to the house and unit. Very clean and a lot of space beds if you have kiddos. 10/10!"
United States
Maddie E.
The price is NZ$282
includes taxes & fees
28 June - 29 June
Benny B Charming 2 Bedroom house bunk/game room close to Ball State University

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (15 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
The price is NZ$559
includes taxes & fees
29 June - 30 June
Charming Home! Prime Location! Dog-Friendly!

'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 NZ$585
includes taxes & fees
25 June - 26 June
'downtown Delight' w/ Patio! 1 Mi to Ball State

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, (17 reviews)
"We had a great time "
United States
cortney C.
The price is NZ$342
includes taxes & fees
30 June - 1 July
Boho Bungalow off Main-one block from Lovely Park

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, (12 reviews)
"Our family had a great stay! "
United States
todd b.
The price is NZ$737
includes taxes & fees
24 June - 25 June
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (37 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 NZ$638
includes taxes & fees
6 July - 7 July
Westcott Mansion with Pickleball Court & Huge Gazebo

Governor's Cabin in Arcanum, Ohio

Governor's Cabin in Arcanum, Ohio
Arcanum
The price is NZ$999
includes taxes & fees
23 June - 24 June
Governor's Cabin in Arcanum, Ohio
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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Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as NZ$282 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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, Burlington Lake and Prairie Creek Reservoir and Campground 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.