Winchester Vacation Rentals

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Sep 19 - Sep 21
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Oct 3 - Oct 5
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Oct 31 - Nov 2
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Nov 28 - Nov 30

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Outdoor dining

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

9.8 out of 10, Exceptional, (193)
"We had a great stay! Ted was very communicative and thoughtful of our needs. The house fit our group perfectly and was so much fun. We enjoyed the games onsite and the indoor pool. We were able to visit and relax. A perfect weekend getaway! "
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Sport court

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

10.0 out of 10, Exceptional, (196)
"An awesome place to stay with a large group. The indoor pickleball was a huge hit!!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Living area

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.0 out of 10, Wonderful, (11)
"Nice, quiet, peaceful."
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
3 br country home close to town with hot tub
Fridge, microwave, oven, stovetop

3 br country home close to town with hot tub

9.4 out of 10, Exceptional, (30)
"Very nice home and I appreciated the small fence yard for my dog."
3 br country home close to town with hot tub
Cardinal Cottage - 2 bedroom cozy home
Exterior

Cardinal Cottage - 2 bedroom cozy home

9.8 out of 10, Exceptional, (21)
"Great stay "
$150 nightly
The price is $168
Sep 7 - Sep 8
Total with taxes and fees
Cardinal Cottage - 2 bedroom cozy home
Boho Bungalow off Main-one block from Lovely Park
Interior

Boho Bungalow off Main-one block from Lovely Park

9.0 out of 10, Wonderful, (11)
"Neighborhood a little blighted. Little house is a great piece of history. Very well maintained, appointed and loved. We were comfortable."
$160 nightly
The price is $179
Sep 7 - Sep 8
Total with taxes and fees
Boho Bungalow off Main-one block from Lovely Park
Pet-Friendly Greenville Home w/ Private Yard
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (21)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard
5 min walk to BSU Campus - Quiet Neighborhood
Dining

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (70)
"A quiet neighborhood with a private back yard and we had everything we needed for a wonderful weekend celebrating a birthday and retirement. Would stay here again!"
5 min walk to BSU Campus - Quiet Neighborhood
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Dining

Updated condo in the heart of Historic District with patio, streaming, fast WiFi

10.0 out of 10, Exceptional, (21)
"Great location. Safe . Easy check in and out process"
$304 nightly
The price is $341
Sep 15 - Sep 16
Total with taxes and fees
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Summer Specials-Guest favorite! Near IU Hospital & Ball State University
Dining

Summer Specials-Guest favorite! Near IU Hospital & Ball State University

10.0 out of 10, Exceptional, (22)
"Stayed for 6 nights. Every thing was super clean. Communication with host was wonderful. I will totally be disappointed at my next stay in Muncie if I’m unable to book this listing. A great place to stay*****"
Summer Specials-Guest favorite! Near IU Hospital & Ball State University
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Interior

Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10

10.0 out of 10, Exceptional, (2)
"We had an AMAZING time at Elm & Ivy!! What a beautiful venue for a chill bachelorette party!! There were so many perfect little touches that added to our stay. Highly recommend- we already talked about coming back again!!"
$400 nightly
The price is $400
Sep 7 - Sep 8
Total with taxes and fees
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
lake front 2 br condo close to bsu
Exterior

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (49)
"This property suited us perfectly as we helped our daughter purchase and move into her new home in Muncie!The location just off McGalliard had everything we could need or want. The accommodations were clean and comfortable!"
lake front 2 br condo close to bsu
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (10)
"We are from Richmond originally and come back to visit family often. Definitely will be back. Great stay, great host, very accommodating, and clean. Highly recommend if you are in the area. "
$294 nightly
The price is $329
Sep 14 - Sep 15
Total with taxes and fees
Charming Home! Prime Location! Dog-Friendly!
Cozy RV close to the Reservoir
Interior

Cozy RV close to the Reservoir

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...
$144 nightly
The price is $161
Sep 5 - Sep 6
Total with taxes and fees
Cozy RV close to the Reservoir
Retro Home Close to Campus
Dining

Retro Home Close to Campus

9.8 out of 10, Exceptional, (6)
"Cute home, a lot of unique features. Great location. Owner was very easy to work with and accommodating to our group. Would totally rent this again ."
$265 nightly
The price is $297
Sep 5 - Sep 6
Total with taxes and fees
Retro Home Close to Campus
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Smart TV, fireplace

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

9.2 out of 10, Wonderful, (20)
"Always a pleasure and the location is perfect for seeing family!"
$124 nightly
The price is $138
Sep 8 - Sep 9
Total with taxes and fees
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Fridge, microwave, oven, stovetop

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

9.8 out of 10, Exceptional, (10)
"Very clean and great amenities. Will be booking there again in the future."
$146 nightly
The price is $164
Sep 8 - Sep 9
Total with taxes and fees
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (2)
"Excellent hospitality and accommodations!It was so nice to have snacks available waiting for us upon arrival. The ice and water options were so nice. We felt so at home in this safe, quiet neighborhood with discreet parking right at the door. Hope to book again when we come to visit our family. Easy access with personalized code provided from owner. Clean, great communication, had everything we needed.Thank you so much."
$148 nightly
The price is $166
Oct 1 - Oct 2
Total with taxes and fees
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Exterior

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

2.0 star property
7.4 out of 10, Good, (3)
"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!!"
$246 nightly
The price is $246
Sep 8 - Sep 9
Total with taxes and fees
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
THE STARR LOFT- Earlham, IUEast, Historic District
Interior

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (32)
"Spacious, Unique property. Incredible location within the Starr Historic Distric of Richmond.Enjoyed the weekend exploring and 5 minutes from the Earlham College Campus."
THE STARR LOFT- Earlham, IUEast, Historic District
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

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 $138 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

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?

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!: 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 Golf Club and Winchester Speedway 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.