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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester vacation rentals

House (1 Bedroom) | Interior

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
$292 nightly
The price is $326
Aug 13 - Aug 14
Total with taxes and fees
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Coffee/tea maker, fridge, microwave, oven

2. 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
$132 nightly
The price is $147
Aug 24 - Aug 25
Total with taxes and fees
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Interior

3. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (41 reviews)
"Really enjoyed my stay "
United States
Deb H.
$150 nightly
The price is $168
Aug 14 - Aug 15
Total with taxes and fees
Cardinal Cottage - 2 bedroom cozy home
TV

4. 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.
$300 nightly
The price is $336
Aug 13 - Aug 14
Total with taxes and fees
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Coffee/tea maker, fridge, microwave, oven

5. 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, (16 reviews)
"We had a great time and this place has everything that you need!"
United States
kirk h.
$146 nightly
The price is $164
Aug 25 - Aug 26
Total with taxes and fees
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Fridge, microwave, oven, stovetop

6. 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)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
$215 nightly
The price is $241
Aug 31 - Sep 1
Total with taxes and fees
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
TV

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, (26 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
$311 nightly
The price is $348
Aug 13 - Aug 14
Total with taxes and fees
'Downtown Delight' w/ Patio! 1 Mi to Ball State
Exterior

8. Cozy 2-bedroom next to Cardinal Greenway.

Cozy 2-bedroom next to Cardinal Greenway.
Muncie
$196 nightly
The price is $220
Sep 2 - Sep 3
Total with taxes and fees
Cozy 2-bedroom next to Cardinal Greenway.
Dining

9. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (13 reviews)
"Nice property no hassel stay!"
United States
Donald D.
$269 nightly
The price is $301
Aug 12 - Aug 13
Total with taxes and fees
Retro Home Close to Campus
Smart TV, books

10. 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.
$204 nightly
The price is $228
Sep 8 - Sep 9
Total with taxes and fees
Quaker Hill Cottage on gated estate with fire pit & hiking trails
2 bedrooms, WiFi, bed sheets

11. 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.
$160 nightly
The price is $179
Aug 31 - Sep 1
Total with taxes and fees
Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
Apartment (2 Bedrooms) | Interior

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

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
$303 nightly
The price is $321
Aug 13 - Aug 14
Total with taxes and fees
'downtown Delight' w/ Patio! 1 Mi to Ball State
Exterior

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

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (17 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
$295 nightly
The price is $330
Aug 14 - Aug 15
Total with taxes and fees
Charming Home! Prime Location! Dog-Friendly!
1 bedroom, WiFi, bed sheets

14. 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
$182 nightly
The price is $204
Aug 13 - Aug 14
Total with taxes and fees
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
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
$297 nightly
The price is $333
Aug 24 - Aug 25
Total with taxes and fees
Westcott Mansion with Pickleball Court & Huge Gazebo
Interior

16. 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.
$432 nightly
The price is $432
Aug 13 - Aug 14
Total with taxes and fees
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Dining

17. Governor's Cabin in Arcanum, Ohio

Governor's Cabin in Arcanum, Ohio
Arcanum
$585 nightly
The price is $585
Aug 12 - Aug 13
Total with taxes and fees
Governor's Cabin in Arcanum, Ohio
Dining

18. 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
$67 nightly
The price is $74
Aug 16 - Aug 17
Total with taxes and fees
King Bed Non-Smoking
1 bedroom

19. 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
$73 nightly
The price is $80
Aug 15 - Aug 16
Total with taxes and fees
2 Queen Beds Non-Smoking
3 bedrooms, iron/ironing board, WiFi, bed sheets

20. 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
$228 nightly
The price is $255
Aug 12 - Aug 13
Total with taxes and fees
Serene 3-bedroom house Cartier with AC in the Village at Ball State University
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
"Nice hotel and well designed room. The area with construction was a bit hard to navigate. Front desk was courteous. Overall, a pleasant stay."
Elizabeth 1-night trip
Posted 1 hour ago
Home2 Suites by Hilton Richmond

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $228 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.