Search Holiday Homes in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Condo image
Condos
Condos
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winchester holiday homes

Living area

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
6.0 out of 10, (2 reviews)
"Our second stay for a family cemetery project.Nice safety improvements since we visited - a railing on the steps to the second floor, a grab bar and mat for the tub.The atmosphere feels homey despite some quirks as a result of the home’s age.Easy stay."
United States
Robert Toy
The price is £234
includes taxes & fees
11 Nov - 12 Nov
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, (47 reviews)
"Everything was perfect!Thank you"
United States
Jeannine F.
The price is £120
includes taxes & fees
12 Nov - 13 Nov
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
10.0 out of 10, Exceptional, (21 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is £210
includes taxes & fees
11 Nov - 12 Nov
Retro Home Close to Campus
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

4. 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, (15 reviews)
"Our family had a great stay! "
United States
todd b.
The price is £304
includes taxes & fees
12 Nov - 13 Nov
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with a view.

5. 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 £176
includes taxes & fees
24 Nov - 25 Nov
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.

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

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (22 reviews)
"Great house in beautiful neighborhood."
United States
Chad H.
The price is £239
includes taxes & fees
11 Nov - 12 Nov
Charming Home! Prime Location! Dog-Friendly!
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

7. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 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 £232
includes taxes & fees
17 Nov - 18 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo
A hot tub on a wooden deck surrounded by a wooden fence with string lights.

8. Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin

Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin
Muncie
10.0 out of 10, Exceptional, (1 review)
"Clean house good location."
United States
Tomasz K.
The price is £294
includes taxes & fees
24 Nov - 25 Nov
Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin
A bedroom with a bed, a TV, a window with curtains, and a view of the outside.

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 £466
includes taxes & fees
24 Nov - 25 Nov
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

Learn more about Winchester

In the heart of small-town America, Winchester's Historic Shopping & Dining District invites visitors to explore local heritage while savouring hometown flavours. Racing enthusiasts can catch high-octane action at Winchester Speedway, while golfers enjoy peaceful rounds at the well-maintained Winchester Golf Club.

See all hotels in Winchester
A historic building with a clock tower, a statue, and well-maintained gardens.

Top reviews in Winchester

A golf course with a pond, trees, and a clear sky.
Randolph Inn and Suites

Randolph Inn and Suites

Randolph Inn and Suites
Winchester

10/10 Excellent

Ideally located for racing at Eldora and Winchester Speedways. Hope to visit again.
United Kingdom
David
Reviewed July 22, 2024
Randolph Inn and Suites