Winchester Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winchester vacation rentals

House (1 Bedroom) | Front of property

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is ￥13,554
￥51,906 total
includes taxes & fees
May 14 - May 15
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Exterior

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (13 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
The price is ￥24,757
￥51,849 total
includes taxes & fees
May 17 - May 18
Charming Home! Prime Location! Dog-Friendly!
Smart TV, books

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, (30 reviews)
"Very easy to find and such a charming home! Very quiet and beautiful area. "
United States
Angie P.
The price is ￥18,077
￥34,683 total
includes taxes & fees
May 21 - May 22
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Exterior

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, (10 reviews)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is ￥24,679
￥38,983 total
includes taxes & fees
May 25 - May 26
Charming 3-bedroom house with AC, WiFi in Greenville
Living area

Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.2 out of 10, Wonderful, (15 reviews)
"We had a great time "
United States
cortney C.
The price is ￥16,033
￥29,400 total
includes taxes & fees
May 19 - May 20
Boho Bungalow off Main-one block from Lovely Park
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, (11 reviews)
"Our family had a great stay! "
United States
todd b.
The price is ￥59,418
￥67,906 total
includes taxes & fees
May 14 - May 15
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
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.
Greenville
9.2 out of 10, Wonderful, (12 reviews)
"Perfect place to relax, close to any store you will need, will def be back"
United States
Jesse G.
The price is ￥22,411
￥36,280 total
includes taxes & fees
May 26 - May 27
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Interior

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (38 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is ￥14,147
￥26,408 total
includes taxes & fees
May 14 - May 15
Cardinal Cottage - 2 bedroom cozy home
TV

'Downtown Delight' w/ Patio! 1 Mi to Ball State

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
10.0 out of 10, Exceptional, (22 reviews)
"Great host and all the amenities were in great condition."
United States
Dan H.
The price is ￥17,291
￥54,105 total
includes taxes & fees
May 17 - May 18
'Downtown Delight' w/ Patio! 1 Mi to Ball State
Dining

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (12 reviews)
"Clean house, good location, fair price for the size. Would definitely stay again!"
United States
Anthony C.
The price is ￥21,221
￥44,894 total
includes taxes & fees
May 14 - May 15
Retro Home Close to Campus
Apartment (2 Bedrooms) | Interior

'downtown Delight' w/ Patio! 1 Mi to Ball State

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
The price is ￥19,227
￥52,862 total
includes taxes & fees
May 17 - May 18
'downtown Delight' w/ Patio! 1 Mi to Ball State
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, (13 reviews)
"House was great for our stay. Communication was fast and excellent. Would recommend for your stay! "
United States
Juliane H.
The price is ￥12,418
￥27,112 total
includes taxes & fees
Jun 9 - Jun 10
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
TV

Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
The price is ￥12,135
￥53,010 total
includes taxes & fees
May 14 - May 15
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Interior

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.
The price is ￥25,936
￥52,287 total
includes taxes & fees
May 25 - May 26
Westcott Mansion with Pickleball Court & Huge Gazebo
Fridge, microwave, oven, stovetop

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.2 out of 10, Wonderful, (22 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
The price is ￥10,217
￥22,887 total
includes taxes & fees
Jun 2 - Jun 3
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Dining

Governor's Cabin in Arcanum, Ohio

Governor's Cabin in Arcanum, Ohio
Arcanum
The price is ￥62,876
￥90,856 total
includes taxes & fees
May 20 - May 21
Governor's Cabin in Arcanum, Ohio
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, (5 reviews)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
The price is ￥17,291
￥37,675 total
includes taxes & fees
May 18 - May 19
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
1 bedroom, WiFi, bed sheets

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
Muncie
The price is ￥17,730
￥32,745 total
includes taxes & fees
May 17 - May 18
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
2 bedrooms, WiFi, bed sheets

Benny B Charming 2 Bedroom house bunk/game room close to Ball State University

Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
Muncie
The price is ￥14,510
￥21,545 total
includes taxes & fees
May 18 - May 19
Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
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

8/10 Good
"Decent hotel, little dated rooms but convenient location. Pool area looked nice, but didn't use. Shower was good, bed was hard."
shannon 1-night trip
Posted 12 hours ago
Baymont by Wyndham Richmond I-70

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

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 Burlington Lake 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.