Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Winchester

Outdoor dining
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Winchester
9.8 out of 10, Exceptional, (196)
"Had a great time. Location is excellent and really enjoyed everything the house had to offer. "
United States
Cade P.
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
A heated pool
Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25

Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25

Fort recovery
10.0 out of 10, Exceptional, (201)
"We had a wonderful time staying here. The pool and gym were amazing!"
United States
James B.
Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25
Interior
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, (4)
"Not only was the property amazing an as advertised but the Host was incredibly nice and accommodating would highly recommend."
United States
Mike S.
$432 nightly
The price is $432
Nov 23 - Nov 24
Total with taxes and fees
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Exterior
Quaker Hill Cottage on gated estate with fire pit & hiking trails

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

Richmond
9.6 out of 10, Exceptional, (27)
"Quaint cottage in Richmond, Indiana. Very peaceful location even though close to downtown. My sisters, our daughters, and I enjoyed spending time in such a beautiful setting."
United States
Judi C.
$239 nightly
The price is $268
Nov 20 - Nov 21
Total with taxes and fees
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Exterior
Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home

Muncie
9.8 out of 10, Exceptional, (27)
"Great stay "
United States
Timothy M.
$150 nightly
The price is $168
Nov 20 - Nov 21
Total with taxes and fees
Cardinal Cottage - 2 bedroom cozy home
Fridge, microwave, oven, stovetop
3 br country home close to town with hot tub

3 br country home close to town with hot tub

Muncie
9.6 out of 10, Exceptional, (32)
"It was great"
Canada
Chris
3 br country home close to town with hot tub
Microwave, oven, stovetop, dishwasher
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, (5)
$145 nightly
The price is $163
Nov 22 - Nov 23
Total with taxes and fees
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Interior
THE STARR LOFT- Earlham, IUEast, Historic District

THE STARR LOFT- Earlham, IUEast, Historic District

Richmond
9.4 out of 10, Exceptional, (36)
"Property is so unique and cozy. We really enjoyed the stay. So much better than a hotel. Location is great. Walkable to many restaurants. Would definitely recommend. "
United States
Renee M.
THE STARR LOFT- Earlham, IUEast, Historic District
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Greenville Home w/ Private Yard

Pet-Friendly Greenville Home w/ Private Yard

Greenville
10.0 out of 10, Exceptional, (24)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
United States
Vernon
Pet-Friendly Greenville Home w/ Private Yard
Dining
Retro Home Close to Campus

Retro Home Close to Campus

Muncie
9.8 out of 10, Exceptional, (8)
"Nice property no hassel stay!"
United States
Donald D.
$265 nightly
The price is $297
Nov 20 - Nov 21
Total with taxes and fees
Retro Home Close to Campus
Exterior
Recently remodeled Colonial-style home with room for the whole family!

Recently remodeled Colonial-style home with room for the whole family!

Richmond
10.0 out of 10, Exceptional, (40)
"Great place. Highly recommend!"
United States
Jon M.
Recently remodeled Colonial-style home with room for the whole family!
Dining
Top-Rated Guest Favorite- Near Ball State & IU Hospital & November Specials

Top-Rated Guest Favorite- Near Ball State & IU Hospital & November Specials

Muncie
10.0 out of 10, Exceptional, (28)
"Great location, very clean, everything you need is there. "
United States
Anonymous traveler
Top-Rated Guest Favorite- Near Ball State & IU Hospital & November Specials
Dining
The University House King Beds+Fast WIFI+W/D

The University House King Beds+Fast WIFI+W/D

Muncie
10.0 out of 10, Exceptional, (13)
"Great host. "
United States
Michelle G.
The University House King Beds+Fast WIFI+W/D
Fridge, microwave, oven, stovetop
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, (1)
"This rental is a great location, blocks away from the Convention Center and many restaurants. The unit is very fresh and clean. Fully stocked with everything you need for a day or weeks. The host is amazing. Super friendly, helpful, and responsive. I highly recommend this rental to anyone staying in Muncie. "
United States
nathan m.
$166 nightly
The price is $183
Dec 1 - Dec 2
Total with taxes and fees
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Exterior
lake front 2 br condo close to bsu

lake front 2 br condo close to bsu

Muncie
9.4 out of 10, Exceptional, (52)
"Very nice condo… "
United States
Diana M.
lake front 2 br condo close to bsu
Terrace/patio
Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!

Richmond
10.0 out of 10, Exceptional, (12)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
$295 nightly
The price is $330
Nov 20 - Nov 21
Total with taxes and fees
Charming Home! Prime Location! Dog-Friendly!
Interior
Cozy RV close to the Reservoir

Cozy RV close to the Reservoir

2.0 star property
Selma
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...
United States
Eleisha G.
$144 nightly
The price is $161
Nov 20 - Nov 21
Total with taxes and fees
Cozy RV close to the Reservoir
Interior
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, (12)
"Lovely house, easy check-in, great location."
United States
Heather S.
$160 nightly
The price is $179
Nov 20 - Nov 21
Total with taxes and fees
Boho Bungalow off Main-one block from Lovely Park
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+

Hagerstown
10.0 out of 10, Exceptional, (11)
"Very clean and great amenities. Will be booking there again in the future."
United States
Lisa B.
$146 nightly
The price is $164
Dec 1 - Dec 2
Total with taxes and fees
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Living area
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

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

Greens Fork
9.0 out of 10, Wonderful, (14)
"The property is stunning and plenty of space for multiple people if needed! Hosts are extremely friendly and great at communicating as well!! Definitely a place you could come back to over and over again!!"
United States
Madison M.
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
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

Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

10/10 Excellent
"Very clean the staff is great, breakfast is good . I get a good night sleep in the bed. And the shower is the best of all.. everything is great"
Angela 1-night trip
Posted 5 days ago
Baymont by Wyndham Richmond I-70

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 $161 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 Mansfield Park 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.