Holiday Rentals in Winchester

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Check prices for these dates

Our top choices for Winchester holiday rentals

1. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is €291
includes taxes & fees
11 Nov - 12 Nov
Pets Welcome! Quiet Economy Home w/ Spacious Yard

2. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
6.0 out of 10, (2 reviews)
"Our second stay for a family cemetery project.Nice safety improvements since we visited - a railing on the steps to the second floor, a grab bar and mat for the tub.The atmosphere feels homey despite some quirks as a result of the home’s age.Easy stay."
United States
Robert Toy
The price is €281
includes taxes & fees
11 Nov - 12 Nov
Pets Welcome! Quiet Economy Home w/ Spacious Yard

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (28 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
The price is €127
includes taxes & fees
1 Dec - 2 Dec
New Hagerstown Apartment - Self Check-in. Sleeps 4+

4. 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, (15 reviews)
"Our family had a great stay! "
United States
todd b.
The price is €362
includes taxes & fees
12 Nov - 13 Nov
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

5. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (47 reviews)
"Everything was perfect!Thank you"
United States
Jeannine F.
The price is €144
includes taxes & fees
12 Nov - 13 Nov
Cardinal Cottage - 2 bedroom cozy home

6. 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, (18 reviews)
"This is a darling place in a wonderful town. It met all of our needs and we'll definitely stay here again."
United States
Tamera
The price is €149
includes taxes & fees
1 Dec - 2 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

7. '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, (28 reviews)
"This place is Awesome! Clean, comfortable, a home away from home. Robert, our host was fantastic and helpful! Would stay here again and again!"
United States
D D.
The price is €269
includes taxes & fees
12 Nov - 13 Nov
'Downtown Delight' w/ Patio! 1 Mi to Ball State

8. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (21 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is €251
includes taxes & fees
11 Nov - 12 Nov
Retro Home Close to Campus

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

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.2 out of 10, Wonderful, (39 reviews)
"Very nice place to spend the night while passing through on Route 70. The Thistlethwaite Falls are only minutes away and were a perfect evening activity after driving all day."
United States
Jon and Keri C.
The price is €190
includes taxes & fees
22 Nov - 23 Nov
Quaker Hill Cottage on gated estate with fire pit & hiking trails

10. 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, (9 reviews)
"The property was absolutely beautiful, just as pictured!!! it’s a must stay."
United States
Simonne S.
The price is €215
includes taxes & fees
1 Dec - 2 Dec
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

11. '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 €262
includes taxes & fees
12 Nov - 13 Nov
'downtown Delight' w/ Patio! 1 Mi to Ball State

12. Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (22 reviews)
"Great house in beautiful neighborhood."
United States
Chad H.
The price is €287
includes taxes & fees
15 Nov - 16 Nov
Charming Home! Prime Location! Dog-Friendly!

13. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 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 €279
includes taxes & fees
16 Nov - 17 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo

14. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
9.8 out of 10, Exceptional, (119 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveller
The price is €67
includes taxes & fees
11 Nov - 12 Nov
2 Queen Beds Non-Smoking

15. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (154 reviews)
"The staff were friendly and helpful throughout our stay. It felt welcoming right away."
United States
Anonymous traveller
The price is €61
includes taxes & fees
11 Nov - 12 Nov
King Bed Non-Smoking

16. Governor's Cabin in Arcanum, Ohio

Governor's Cabin in Arcanum, Ohio
Arcanum
The price is €641
includes taxes & fees
22 Nov - 23 Nov
Governor's Cabin in Arcanum, Ohio

17. Serene 3-bedroom house Cartier with AC in the Village at Ball State University

Serene 3-bedroom house Cartier with AC in the Village at Ball State University
Muncie
The price is €563
includes taxes & fees
23 Nov - 24 Nov
Serene 3-bedroom house Cartier with AC in the Village at Ball State University

18. 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 €213
includes taxes & fees
23 Nov - 24 Nov
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

19. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (5 reviews)
The price is €60
includes taxes & fees
11 Nov - 12 Nov
2 Queen Beds | Non-Smoking

20. Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin

Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin
Muncie
10.0 out of 10, Exceptional, (1 review)
"Clean house good location."
United States
Tomasz K.
Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin
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.

Find holiday rentals that suit your style

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 €59 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 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.