Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Cottage in Muncie

10.0 out of 10, Exceptional, (5)
The price is €154
includes taxes & fees
24 Nov - 25 Nov
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

Apartment in Hagerstown

10.0 out of 10, Exceptional, (11)
"Very clean and great amenities. Will be booking there again in the future."
United States
Lisa B.
The price is €172
includes taxes & fees
19 Dec - 20 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Apartment in Hagerstown

9.2 out of 10, Wonderful, (20)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is €157
includes taxes & fees
19 Dec - 20 Dec
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Holiday Home in Muncie

9.8 out of 10, Exceptional, (28)
"Great stay "
United States
Timothy M.
The price is €150
includes taxes & fees
4 Dec - 5 Dec
Cardinal Cottage - 2 bedroom cozy home

Cottage in Richmond

9.6 out of 10, Exceptional, (28)
"Quaint cottage in Richmond, Indiana. Very peaceful location even though close to downtown. My sisters, our daughters, and I enjoyed spending time in such a beautiful setting."
United States
Judi C.
The price is €237
includes taxes & fees
25 Nov - 26 Nov
Quaker Hill Cottage on gated estate with fire pit & hiking trails

Holiday Home in Richmond

9.0 out of 10, Wonderful, (12)
"Lovely house, easy check-in, great location."
United States
Heather S.
The price is €159
includes taxes & fees
23 Nov - 24 Nov
Boho Bungalow off Main-one block from Lovely Park

Apartment in Muncie

10.0 out of 10, Exceptional, (1)
"This rental is a great location, blocks away from the Convention Center and many restaurants. The unit is very fresh and clean. Fully stocked with everything you need for a day or weeks. The host is amazing. Super friendly, helpful, and responsive. I highly recommend this rental to anyone staying in Muncie. "
United States
nathan m.
The price is €165
includes taxes & fees
4 Dec - 5 Dec
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Holiday Home in Richmond

10.0 out of 10, Exceptional, (12)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is €293
includes taxes & fees
22 Nov - 23 Nov
Charming Home! Prime Location! Dog-Friendly!

Mobile Home in Selma

2.0 star property
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 €143
includes taxes & fees
4 Dec - 5 Dec
Cozy RV close to the Reservoir

Holiday Home in Greenville

2.0 star property
9.0 out of 10, Wonderful, (8)
"This is a beautiful home with exceptional amenities. Is just about the closest home to the fairgrounds. Does need a gas grill.Thank you for letting us stay!!"
United States
Tonia E.
The price is €219
includes taxes & fees
2 Dec - 3 Dec
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Condo in Muncie

10.0 out of 10, Exceptional, (24)
"Stayed multiple times, always great, the owners are amazing and helpful."
United States
Randy G.
Updated condo in the heart of Historic District with patio, streaming, fast WiFi

Holiday Home in 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 €207
includes taxes & fees
4 Dec - 5 Dec
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus

Holiday Home in Richmond

9.8 out of 10, Exceptional, (34)
"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 €296
includes taxes & fees
25 Nov - 26 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo

Holiday Home in Muncie

9.8 out of 10, Exceptional, (9)
"Nice property no hassel stay!"
United States
Donald D.
The price is €267
includes taxes & fees
22 Nov - 23 Nov
Retro Home Close to Campus

Holiday Home in Muncie

The price is €179
includes taxes & fees
4 Dec - 5 Dec
Charming 2-bedroom house in Muncie with bunk-game room close to Ball State

Holiday Home in Greenville

9.0 out of 10, Wonderful, (8)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is €221
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house with AC, WiFi in Greenville

Holiday Home in Fort Recovery

10.0 out of 10, Exceptional, (4)
"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 €385
includes taxes & fees
23 Nov - 24 Nov
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

Holiday Home in Delaware Township

The price is €1,024
includes taxes & fees
4 Dec - 5 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

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, apart-hotels, 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 €143 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, Prairie Creek Reservoir and Campground and Mansfield 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.