Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

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, (194)
"We wanted a location to gather our whole family of 40 to celebrate our 50th anniversary and this fit the bill exactly. Far enough away from home to feel removed but close enough for reasonable travel. The owner was VERY responsive to an issue that popped up and took care of it immediately. "
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
A heated pool

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

10.0 out of 10, Exceptional, (198)
"We were impressed with the size of the pool and with the gym! Our teenagers loved both a lot!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
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)
"Great place, great location, awesome hosts."
3 br country home close to town with hot tub
Near Ball State & IU Hospital • Fall Specials • Top-Rated Guest Favorite
Dining

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

10.0 out of 10, Exceptional, (23)
"The house was clean, nicely remodeled and had everything we needed. It was also a great location and near everything we wanted to be. They had fun games, an awesome back yard and covered parking. Highly recommend!"
Near Ball State & IU Hospital • Fall Specials • Top-Rated Guest Favorite
lake front 2 br condo close to bsu
Exterior

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (49)
"10/10"
lake front 2 br condo close to bsu
Cardinal Cottage - 2 bedroom cozy home
Exterior

Cardinal Cottage - 2 bedroom cozy home

9.8 out of 10, Exceptional, (26)
"Great stay "
The price is ￥13,285
￥24,799 total
includes taxes & fees
Sep 28 - Sep 29
Cardinal Cottage - 2 bedroom cozy home
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."
The price is ￥12,238
￥24,453 total
includes taxes & fees
Oct 8 - Oct 9
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
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.

8.6 out of 10, Excellent, (39)
"I held a memorial service for my recently deceased wife. This was the perfect spot for my family to gather. Room for visiting kids to run and adults to talk. Thanks again!"
3-bedroom vacation home 9 minutes from Ball State University in the country.
Pet-Friendly Greenville Home w/ Private Yard
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (22)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard
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)
"We very much enjoyed our 1 night visit at the Boho Bungalow! The house was cozy and charming. Everything was clean and the property host gave clear information for our stay. We highly recommend this location."
The price is ￥14,023
￥26,452 total
includes taxes & fees
Sep 25 - Sep 26
Boho Bungalow off Main-one block from Lovely Park
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, (12)
"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!!"
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Exterior

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

9.8 out of 10, Exceptional, (25)
"Very unique quaint cottage hidden from the city. Loved the forested area around it with the patio to the side. We saw"
The price is ￥16,975
￥32,238 total
includes taxes & fees
Sep 25 - Sep 26
Quaker Hill Cottage on gated estate with fire pit & hiking trails
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
8.8 out of 10, Excellent, (6)
"Didn’t get in the house"
The price is ￥22,850
￥36,135 total
includes taxes & fees
Sep 29 - Sep 30
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
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, (22)
"Great location. Safe . Easy check in and out process"
The price is ￥18,451
￥50,431 total
includes taxes & fees
Oct 1 - Oct 2
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie
Fridge, microwave, oven, coffee/tea maker

Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie

7.0 out of 10, Good, (8)
"Wonderful property close to everything and super clean. Owners are great communicators and helpful with information. We will stay again soon."
Cozy 2-bedroom bungalow with WiFi and AC in delightful Muncie
The University House King Beds+Fast WIFI+W/D
Dining

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

10.0 out of 10, Exceptional, (10)
"Great host. "
The University House King Beds+Fast WIFI+W/D
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!!"
The price is ￥51,664
￥59,045 total
includes taxes & fees
Oct 5 - Oct 6
Ft Recovery’s Historic Chapel with Speakeasy Hideaway - Host 40 guests/Sleeps 10
Pet-friendly Greenville Home w/ Private Yard
House (3 Bedrooms) | Interior

Pet-friendly Greenville Home w/ Private Yard

3.0 star property
Pet-friendly Greenville Home w/ Private Yard
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (10)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
The price is ￥23,249
￥48,524 total
includes taxes & fees
Sep 29 - Sep 30
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...
The price is ￥15,278
￥23,726 total
includes taxes & fees
Sep 25 - Sep 26
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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Top Winchester Hotel Reviews

Comfort Suites

Comfort Suites

10/10 Excellent
"The staff was friendly and courteous it was clean and comfortable "
Robert 2-night trip
Posted 3 days ago
Comfort Suites

Find out more about Winchester

Find out more about Winchester

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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.

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.