Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Winchester vacation rentals

Interior
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Muncie
10.0 out of 10, Exceptional, (7 reviews)
"The place was super clean, the bed was really comfortable, and the bathroom was big and well-maintained. The host gave me the necessary info before I needed to ask for it which is not always the case. It is located really close to Ball State. If my daughter chooses to go to school there we will be staying here for sure!"
United States
Julie H.
$145 nightly
The price is $163
Jan 25 - Jan 26
Total with taxes and fees
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Fridge, microwave, oven, stovetop
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 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, (11 reviews)
"Very conveniently located with clear instructions about amenities. We will stay here again sometime."
United States
MaryandMichael P.
$146 nightly
The price is $164
Jan 12 - Jan 13
Total with taxes and fees
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Interior
Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (34 reviews)
"Very clean and easy weekend stay"
United States
Ally B.
$150 nightly
The price is $168
Jan 12 - Jan 13
Total with taxes and fees
Cardinal Cottage - 2 bedroom cozy home
Fridge, microwave, oven, stovetop
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

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, (4 reviews)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
$186 nightly
The price is $208
Jan 13 - Jan 14
Total with taxes and fees
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Fridge, microwave, oven, stovetop
New Hagerstown Apartment - Self Check-in. Sleeps 4+

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.2 out of 10, Wonderful, (20 reviews)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
$130 nightly
The price is $145
Jan 21 - Jan 22
Total with taxes and fees
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Living area
Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.0 out of 10, Wonderful, (14 reviews)
"Lovely house, easy check-in, great location."
United States
Heather S.
Boho Bungalow off Main-one block from Lovely Park
Apartment (2 Bedrooms) | Interior
2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D
2.5 star property
Muncie
$302 nightly
The price is $335
Jan 18 - Jan 19
Total with taxes and fees
2BR Updated Dtwn Condo: Streaming, Patio, W & D
Smart TV, foosball
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
2.0 star property
Greenville
9.0 out of 10, Wonderful, (10 reviews)
"Comfy and clean!"
United States
rey v.
$246 nightly
The price is $246
Jan 19 - Jan 20
Total with taxes and fees
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Dining
Retro Home Close to Campus

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (10 reviews)
"Nice property no hassel stay!"
United States
Donald D.
$265 nightly
The price is $297
Jan 12 - Jan 13
Total with taxes and fees
Retro Home Close to Campus
Interior
Cozy RV close to the Reservoir

Cozy RV close to the Reservoir

Cozy RV close to the Reservoir
2.0 star property
Selma
6.0 out of 10, (1 review)
"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.
$144 nightly
The price is $161
Jan 12 - Jan 13
Total with taxes and fees
Cozy RV close to the Reservoir
Fridge, microwave, oven, stovetop
Settle in at the Petite Retreat.

Settle in at the Petite Retreat.

Settle in at the Petite Retreat.
Muncie
10.0 out of 10, Exceptional, (28 reviews)
"Property was accurately described and perfect for our stay in muncie. Bed was comfortable l, kitchen was well appointed, and bath towels were plentiful. Looking forward to staying here again. Mari is an excellent communicator."
United States
Kevin Holly K.
$286 nightly
The price is $320
Feb 2 - Feb 3
Total with taxes and fees
Settle in at the Petite Retreat.
Exterior
Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville
Greenville
9.0 out of 10, Wonderful, (8 reviews)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
$248 nightly
The price is $248
Jan 12 - Jan 13
Total with taxes and fees
Charming 3-bedroom house with AC, WiFi in Greenville
TV
2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D
2.0 star property
Muncie
10.0 out of 10, Exceptional, (17 reviews)
"Great apartment with everything needed for a restful stay!"
United States
David G.
$284 nightly
The price is $315
Jan 18 - Jan 19
Total with taxes and fees
2BR Updated Dtwn Condo: Streaming, Patio, W & D
Exterior
Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (13 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
$295 nightly
The price is $330
Jan 16 - Jan 17
Total with taxes and fees
Charming Home! Prime Location! Dog-Friendly!
Interior
Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (35 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.
$297 nightly
The price is $333
Jan 16 - Jan 17
Total with taxes and fees
Westcott Mansion with Pickleball Court & Huge Gazebo
Dining
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus

Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus

Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Muncie
10.0 out of 10, Exceptional, (1 review)
"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.
$188 nightly
The price is $211
Jan 20 - Jan 21
Total with taxes and fees
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Interior
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

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, (9 reviews)
"This place is a hidden gem! Would definitely host a gathering here again :)"
United States
Rachel S.
$360 nightly
The price is $360
Jan 13 - Jan 14
Total with taxes and fees
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
2 bedrooms, WiFi, bed sheets
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State

Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State

Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
Muncie
$174 nightly
The price is $195
Jan 12 - Jan 13
Total with taxes and fees
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
Exterior
Country living 4 Bedroom House

Country living 4 Bedroom House

Country living 4 Bedroom House
Delaware Township
$1,028 nightly
The price is $1,151
Jan 12 - Jan 13
Total with taxes and fees
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

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN

10/10 Excellent
"Consistently good breakfast options. Convenient location. Nice suites for family of 4. Pet friendly. "
Sandra 1-night trip
Posted 7 days ago
Hampton Inn & Suites Richmond, IN

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 $145 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 Turkeyfoot Preserve 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.