Default HTG hotel image

Winchester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation homes

1. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
2.0 out of 10, (1 review)
"Bed bugs in upstairs bedroom!!!Unfortunately we had a terrible experience both during and following our stay. During the stay the air conditioning was not functioning properly and we were forced to use portable AC units that didn’t get the temperature below 78 in the house.Three people sleeping upstairs had bed bug bites and upon searching the two beds we found numerous bugs. We promptly made the property owner aware of the situation and requested our stay be refunded due to the inconvenience...
United States
Payton L.
The price is CA $107
CA $462 total
includes taxes & fees
Aug 30 - Aug 31
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A living room with hardwood flooring, a leather sofa, a mounted TV, and a door leading to a kitchen.

2. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (43 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is CA $125
CA $233 total
includes taxes & fees
Aug 31 - Sep 1
Cardinal Cottage - 2 bedroom cozy home
A dining area with a table set for four, chairs, and a patterned wallpaper.

3. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (16 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is CA $187
CA $413 total
includes taxes & fees
Aug 30 - Aug 31
Retro Home Close to Campus
A hotel room with a bed, bedside tables, an air conditioning unit, a painting on the wall, and a television.

4. 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
9.4 out of 10, Exceptional, (3 reviews)
"Such a cute little stay! Super easy and clear access to parking and the access to the house and unit. Very clean and a lot of space beds if you have kiddos. 10/10!"
United States
Maddie E.
The price is CA $167
CA $234 total
includes taxes & fees
Aug 31 - Sep 1
Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

5. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (40 reviews)
"This is a wonderful historic property if you're into a vintage stay. We were. The home is lovely. The only disadvantages are not having a host on-site and having to get luggage up the stairs without an elevator or bellhop assitance; there are no bedrooms on the ground floor. And being vintage, it takes quite a while to adjust the temperature to where you want it. Also, it would be helpful to have television instructions; we were never able to figure out how to get anything on the TV."
United States
Debbie
The price is CA $229
CA $459 total
includes taxes & fees
Aug 31 - Sep 1
Westcott Mansion with Pickleball Court & Huge Gazebo
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with a view.

6. 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 CA $173
CA $279 total
includes taxes & fees
Aug 29 - Aug 30
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

7. Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (19 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
The price is CA $218
CA $449 total
includes taxes & fees
Sep 5 - Sep 6
Charming Home! Prime Location! Dog-Friendly!
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

8. 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, (14 reviews)
"Our family had a great stay! "
United States
todd b.
The price is CA $524
CA $596 total
includes taxes & fees
Sep 1 - Sep 2
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

9. Serene 3-bedroom house Cartier with AC in the Village at Ball State University

Serene 3-bedroom house Cartier with AC in the Village at Ball State University
Muncie
The price is CA $262
CA $349 total
includes taxes & fees
Aug 30 - Aug 31
Serene 3-bedroom house Cartier with AC in the Village at 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Quality Inn and Conference Center

Quality Inn and Conference Center

8/10 Good
"Enjoyed our four day, three night stay at the Quality Inn Richmond, IN. Great location on the National Road/U.S. 40 convenient to shopping/restaurants and other amenities. Nice comfortable beds and room, quiet and the price was hard to beat for the comfort of the room and beds. Nice complimentary breakfasts."
Dale 3-night trip
Posted 2 hours ago
Quality Inn and Conference Center

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
122
Accommodation
45 Vacation Homes
Lowest Price
CA $233
Highest Price
CA $596

Explore a world of travel with Expedia