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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winchester vacation rentals

Dining

1. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (151 reviews)
"Had everything we needed for our visit,non smoking rooms kept things fresh too!"
United States
Anonymous traveler
The price is ￥9,210
￥11,824 total
includes taxes & fees
Aug 23 - Aug 24
King Bed Non-Smoking
1 bedroom

2. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (115 reviews)
"Came for a short break and appreciated having the comforts of home close by!"
United States
Anonymous traveler
The price is ￥9,965
￥12,809 total
includes taxes & fees
Aug 24 - Aug 25
2 Queen Beds Non-Smoking
Interior

3. 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 ￥30,130
￥40,709 total
includes taxes & fees
Aug 24 - Aug 25
Serene 3-bedroom house Cartier with AC in the Village at Ball State University
House (1 Bedroom) | Interior

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is ￥17,217
￥52,045 total
includes taxes & fees
Aug 20 - Aug 21
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Coffee/tea maker, fridge, microwave, oven

5. 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 ￥10,474
￥23,338 total
includes taxes & fees
Sep 1 - Sep 2
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Coffee/tea maker, fridge, microwave, oven

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, (17 reviews)
"We had a great time and this place has everything that you need!"
United States
kirk h.
The price is ￥11,335
￥26,088 total
includes taxes & fees
Aug 25 - Aug 26
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Interior

7. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (43 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is ￥14,348
￥26,783 total
includes taxes & fees
Aug 20 - Aug 21
Cardinal Cottage - 2 bedroom cozy home
TV

8. '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, (26 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is ￥17,536
￥55,529 total
includes taxes & fees
Aug 30 - Aug 31
'Downtown Delight' w/ Patio! 1 Mi to Ball State
TV

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
2.0 out of 10, (1 review)
"Bed bugs in upstairs bedroom!!!Unfortunately we had a terrible experience both during and following our stay. During the stay the air conditioning was not functioning properly and we were forced to use portable AC units that didn’t get the temperature below 78 in the house.Three people sleeping upstairs had bed bug bites and upon searching the two beds we found numerous bugs. We promptly made the property owner aware of the situation and requested our stay be refunded due to the inconvenience...
United States
Payton L.
The price is ￥12,275
￥53,565 total
includes taxes & fees
Aug 21 - Aug 22
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Fridge, microwave, oven, stovetop

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, (8 reviews)
"The property was absolutely beautiful, just as pictured!!! it’s a must stay."
United States
Simonne S.
The price is ￥18,971
￥38,567 total
includes taxes & fees
Aug 31 - Sep 1
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Smart TV, books

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

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.4 out of 10, Exceptional, (34 reviews)
"Very easy to find and such a charming home! Very quiet and beautiful area. "
United States
Angie P.
The price is ￥18,511
￥35,924 total
includes taxes & fees
Sep 9 - Sep 10
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Dining

12. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (14 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is ￥21,522
￥48,030 total
includes taxes & fees
Aug 20 - Aug 21
Retro Home Close to Campus
Exterior

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

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (19 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
The price is ￥25,109
￥52,585 total
includes taxes & fees
Aug 20 - Aug 21
Charming Home! Prime Location! Dog-Friendly!
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

14. Cozy 2-bedroom next to Cardinal Greenway.

Cozy 2-bedroom next to Cardinal Greenway.
Muncie
The price is ￥19,150
￥34,853 total
includes taxes & fees
Sep 2 - Sep 3
Cozy 2-bedroom next to Cardinal Greenway.
Interior

15. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (40 reviews)
"This is a wonderful historic property if you're into a vintage stay. We were. The home is lovely. The only disadvantages are not having a host on-site and having to get luggage up the stairs without an elevator or bellhop assitance; there are no bedrooms on the ground floor. And being vintage, it takes quite a while to adjust the temperature to where you want it. Also, it would be helpful to have television instructions; we were never able to figure out how to get anything on the TV."
United States
Debbie
The price is ￥26,304
￥53,029 total
includes taxes & fees
Aug 24 - Aug 25
Westcott Mansion with Pickleball Court & Huge Gazebo
2 bedrooms, WiFi, bed sheets

16. 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
9.4 out of 10, Exceptional, (3 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 ￥20,725
￥28,568 total
includes taxes & fees
Aug 31 - Sep 1
Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
1 bedroom, WiFi, bed sheets

17. 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 ￥19,928
￥32,497 total
includes taxes & fees
Aug 20 - Aug 21
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
Apartment (2 Bedrooms) | Interior

18. '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 ￥23,913
￥51,159 total
includes taxes & fees
Aug 20 - Aug 21
'downtown Delight' w/ Patio! 1 Mi to Ball State
Interior

19. 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, (14 reviews)
"Our family had a great stay! "
United States
todd b.
The price is ￥60,261
￥68,551 total
includes taxes & fees
Aug 20 - Aug 21
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Dining

20. Governor's Cabin in Arcanum, Ohio

Governor's Cabin in Arcanum, Ohio
Arcanum
The price is ￥44,638
￥70,847 total
includes taxes & fees
Aug 20 - Aug 21
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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Top Winchester Hotel Reviews

Hampton Inn & Suites Muncie

Hampton Inn & Suites Muncie

10/10 Excellent
"We enjoyed a pleasant, mid-week, quiet stay. Continental Breakfast was good & our room was clean. It was recommended by my husband’s manager to stay here."
Stacy 1-night trip
Posted 7 hours ago
Hampton Inn & Suites Muncie

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 vacation rentals in Winchester?

Yes, we give you a choice of vacation rentals close to popular points of interest in Winchester, or you can choose a more secluded option if you're looking for relaxation. Winchester is known for its golf courses.

What's the top vacation rental that Winchester has to offer?

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA: Visitors like this Winchester vacation home rental. It is located in a rural location and has an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 vacation rental in Winchester like?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Winchester. Vacation rentals provide amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.