Winchester Vacation Rentals

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Check prices for these dates

Tonight
Jun 23 - Jun 24
Tomorrow
Jun 24 - Jun 25
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Winchester

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, (185)
"Plenty of room for our 25 that stayed. The pool is wonderful. Very clean and communication is excellent. This was our second stay and will do it again. Thank you Ted"
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
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.

9.8 out of 10, Exceptional, (8)
"The atmosphere and views are stunning. The home is spacious for families. We enjoyed our stay. "
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
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, (190)
"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
Cardinal Cottage - 2 bedroom cozy home
Exterior

Cardinal Cottage - 2 bedroom cozy home

9.6 out of 10, Exceptional, (15)
"Cutest cottage and fabulous hosts went above and beyond for us! Thank you Cole and Margee!"
The price is ￥13,148
￥24,543 total
includes taxes & fees
Jun 29 - Jun 30
Cardinal Cottage - 2 bedroom cozy home
Quaint Economy Retreat w/ Patio & Spacious Yard!
Fridge, microwave, oven, stovetop

Quaint Economy Retreat w/ Patio & Spacious Yard!

9.4 out of 10, Exceptional, (6)
"It was a great place out away from town but close enough you can make it into Richmond with a 15-20 min easy drive "
Quaint Economy Retreat w/ Patio & Spacious Yard!
5 min walk to BSU Campus - Quiet Neighborhood
Property grounds

5 min walk to BSU Campus - Quiet Neighborhood

10.0 out of 10, Exceptional, (64)
"Very close to Ball State, very nice location. Spacious bedrooms, comfortable living spaces. It has a nice 'home' feel to it, warm and welcoming. I hope it is available the next time we are going to be in the area. Thank you!"
5 min walk to BSU Campus - Quiet Neighborhood
THE STARR LOFT- Earlham, IUEast, Historic District
Fridge, microwave, oven, stovetop

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (25)
"I wasn't expecting that a visit to my small hometown would end up being the nicest vacation stay I've had but it was. Walking distance to some fun restaurants and a great record store. Property itself was beautiful and well maintained in a renovated loft space. Lots of charm and attention to detail. This place makes me want to find reasons to visit Richmond more often!"
THE STARR LOFT- Earlham, IUEast, Historic District
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
TV

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

10.0 out of 10, Exceptional, (14)
"Location and condo was perfect. "
The price is ￥16,362
￥47,266 total
includes taxes & fees
Jun 24 - Jun 25
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, (19)
"The house is very clean and comfortably furnished. Hosts were attentive and responsive. I hope to stay there again."
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, (1)
"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!!"
The price is ￥51,132
￥58,437 total
includes taxes & fees
Jun 25 - Jun 26
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Westcott Mansion with Pickleball Court & Huge Gazebo
8 bedrooms, WiFi, bed sheets

Westcott Mansion with Pickleball Court & Huge Gazebo

10.0 out of 10, Exceptional, (31)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
The price is ￥24,105
￥48,596 total
includes taxes & fees
Jul 3 - Jul 4
Westcott Mansion with Pickleball Court & Huge Gazebo
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
6.0 out of 10, (2)
"Didn’t get in the house"
The price is ￥22,615
￥35,763 total
includes taxes & fees
Jun 24 - Jun 25
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
lake front 2 br condo close to bsu
Exterior

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (43)
"If mattresses are replaced, rating would be Excellent!"
lake front 2 br condo close to bsu
The Red House
Property grounds

The Red House

9.6 out of 10, Exceptional, (18)
"This was our 2nd stay at the red house while in town to visit family. Perfect location and space for our family of four. Friendly communication with the owner. Would happily stay again. Recommend!"
The price is ￥14,463
￥33,160 total
includes taxes & fees
Jul 6 - Jul 7
The Red House
3-bedroom vacation home 9 minutes from Ball State University in the country.
Fridge, microwave, oven, stovetop

3-bedroom vacation home 9 minutes from Ball State University in the country.

9.0 out of 10, Wonderful, (34)
"Had Thanksgiving with the family, lots of room. Love the quiet surroundings "
3-bedroom vacation home 9 minutes from Ball State University in the country.
Boho Bungalow off Main-one block from Lovely Park
Interior

Boho Bungalow off Main-one block from Lovely Park

9.2 out of 10, Wonderful, (7)
"We liked the cleanliness of the property. There is also plenty of things to do and great places to eat with in a short distance of the property"
The price is ￥13,879
￥26,180 total
includes taxes & fees
Jun 30 - Jul 1
Boho Bungalow off Main-one block from Lovely Park
3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table
Outdoor dining

3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table

10.0 out of 10, Exceptional, (3)
"This delightful home made a great homebase for our busy weekend prepping and attending our neice’s wedding. It was close to the venue and was a comfy place to watch a movie and chat after our busy days. Hubby was a bit disappointed about not having access to ping pong, but we didn’t have a ton of free time to play anyway. We would stay here again if in the area."
3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table
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, (8)
"Very clean and great amenities. Will be booking there again in the future."
The price is ￥10,387
￥23,906 total
includes taxes & fees
Jun 24 - Jun 25
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Newly renovated studio in Hagerstown--Self Check-in
Fridge, microwave, oven, stovetop

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"Cute place. Property manager very responsive to needs. Great stay."
The price is ￥8,020
￥19,618 total
includes taxes & fees
Jun 30 - Jul 1
Newly renovated studio in Hagerstown--Self Check-in
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...
The price is ￥15,120
￥23,481 total
includes taxes & fees
Jun 24 - Jun 25
Cozy RV close to the Reservoir
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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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.

How many vacation rentals are there in Winchester?

Expedia has 3 vacation rentals for your stay in Winchester.

What’s there to see and do in Winchester?

While you're exploring the area, Prairie Creek Reservoir and Campground and YOLO 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.