Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester vacation rentals

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, (12 reviews)
"Very conveniently located with clear instructions about amenities. We will stay here again sometime."
United States
MaryandMichael P.
The price is ￥11,820
￥26,219 total
includes taxes & fees
Feb 16 - Feb 17
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Interior

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, (7 reviews)
"The place was super clean, the bed was really comfortable, and the bathroom was big and well-maintained. The host gave me the necessary info before I needed to ask for it which is not always the case. It is located really close to Ball State. If my daughter chooses to go to school there we will be staying here for sure!"
United States
Julie H.
The price is ￥12,376
￥25,111 total
includes taxes & fees
Feb 25 - Feb 26
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
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, (21 reviews)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is ￥9,039
￥21,374 total
includes taxes & fees
Feb 24 - Feb 25
New Hagerstown Apartment - Self Check-in. Sleeps 4+
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, (4 reviews)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
The price is ￥17,489
￥34,453 total
includes taxes & fees
Feb 17 - Feb 18
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Fridge, microwave, oven, stovetop

3 Bedroom House in Fort Recovery

3 Bedroom House in Fort Recovery
Fort Recovery
10.0 out of 10, Exceptional, (23 reviews)
"Great!"
United States
Neil D.
The price is ￥20,859
￥42,189 total
includes taxes & fees
Feb 12 - Feb 13
3 Bedroom House in Fort Recovery
Apartment (2 Bedrooms) | Interior

2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D
2.5 star property
Muncie
The price is ￥18,850
￥51,826 total
includes taxes & fees
Feb 18 - Feb 19
2BR Updated Dtwn Condo: Streaming, Patio, W & D
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)
"Lovely house, easy check-in, great location."
United States
Heather S.
The price is ￥14,678
￥27,688 total
includes taxes & fees
Mar 7 - Mar 8
Boho Bungalow off Main-one block from Lovely Park
Interior

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (35 reviews)
"Very clean and easy weekend stay"
United States
Ally B.
The price is ￥13,906
￥25,958 total
includes taxes & fees
Feb 22 - Feb 23
Cardinal Cottage - 2 bedroom cozy home
TV

2BR Updated Dtwn Condo: Streaming, Patio, W & D

2BR Updated Dtwn Condo: Streaming, Patio, W & D
Muncie
10.0 out of 10, Exceptional, (18 reviews)
"Great host and all the amenities were in great condition."
United States
Dan H.
The price is ￥16,996
￥53,355 total
includes taxes & fees
Feb 25 - Feb 26
2BR Updated Dtwn Condo: Streaming, Patio, W & D
Exterior

Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville
Greenville
9.2 out of 10, Wonderful, (9 reviews)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is ￥24,258
￥38,318 total
includes taxes & fees
Feb 14 - Feb 15
Charming 3-bedroom house with AC, WiFi in Greenville
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 ￥25,494
￥49,492 total
includes taxes & fees
Feb 19 - Feb 20
Westcott Mansion with Pickleball Court & Huge Gazebo
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, (11 reviews)
"House was perfect for our family to stay for our daughter's wedding "
United States
Molly L.
The price is ￥23,918
￥37,978 total
includes taxes & fees
Feb 18 - Feb 19
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Dining

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (10 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is ￥20,859
￥45,859 total
includes taxes & fees
Feb 25 - Feb 26
Retro Home Close to Campus
Exterior

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (13 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is ￥24,335
￥50,965 total
includes taxes & fees
Feb 18 - Feb 19
Charming Home! Prime Location! Dog-Friendly!
Interior

Cozy RV close to the Reservoir

Cozy RV close to the Reservoir
Selma
6.0 out of 10, (1 review)
"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.
The price is ￥15,992
￥24,835 total
includes taxes & fees
Feb 13 - Feb 14
Cozy RV close to the Reservoir
Dining

Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus

Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Muncie
10.0 out of 10, Exceptional, (1 review)
"House is cute - loved all the wood floors although they're noisy. beds were comfortable. only stayed one night but it was walkable back and forth to campus so that was great"
United States
Abi Z.
The price is ￥22,249
￥33,398 total
includes taxes & fees
Feb 16 - Feb 17
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
2 bedrooms, WiFi, bed sheets

Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State

Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
Muncie
The price is ￥15,740
￥34,943 total
includes taxes & fees
Feb 16 - Feb 17
Benny B Charming 2-bedroom house in Muncie w/ bunk-game room close to Ball State
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, (9 reviews)
"Not only was the property amazing an as advertised but the Host was incredibly nice and accommodating would highly recommend."
United States
Mike S.
The price is ￥48,671
￥55,624 total
includes taxes & fees
Feb 15 - Feb 16
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Exterior

Country living 4 Bedroom House

Country living 4 Bedroom House
Delaware Township
The price is ￥139,059
￥175,128 total
includes taxes & fees
Feb 18 - Feb 19
Country living 4 Bedroom House
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

Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70

10/10 Excellent
"Both true"
Jeffrey 1-night trip
Posted 4 days ago
Best Western Plus Richmond Indiana I-70

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?

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 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.