A historic building with a clock tower, a statue, and well-maintained gardens.

Holiday Homes in Winchester

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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 AU$460
includes taxes & fees
8 Nov - 9 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)
"Really enjoyed my stay "
United States
Deb H.
The price is AU$242
includes taxes & fees
28 Oct - 29 Oct
Cardinal Cottage - 2 bedroom cozy home
A wooden structure with a covered entrance, a sign indicating a 'Backyard Garden', and potted plants with flowers.

3. Private Cottage - 10-minute walk to Minnetrista

Private Cottage - 10-minute walk to Minnetrista
Muncie
10.0 out of 10, Exceptional, (1 review)
"Hostess was wonderful to communicate with! Cute place & loved it was pet friendly."
United States
julie
The price is AU$246
includes taxes & fees
27 Oct - 28 Oct
Private Cottage - 10-minute walk to Minnetrista
A dining area with a table set for four, chairs, and a patterned wallpaper.

4. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (18 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is AU$423
includes taxes & fees
27 Oct - 28 Oct
Retro Home Close to Campus
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

5. 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 AU$594
includes taxes & fees
27 Oct - 28 Oct
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
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)
"This property was very cozy & clean. We cant wait to come back here again.Lovely space well appointedThe native garden is gorgeousEverything in the house is well cared forBeds Very comfortable.It was fabulous!"
United States
Dyan P.
The price is AU$464
includes taxes & fees
29 Oct - 30 Oct
Charming Home! Prime Location! Dog-Friendly!
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with a view.

7. 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 AU$356
includes taxes & fees
4 Nov - 5 Nov
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

8. 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 AU$457
includes taxes & fees
2 Nov - 3 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo
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 AU$634
includes taxes & fees
9 Nov - 10 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.
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Top Winchester Hotel Reviews

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

10/10 Excellent
"Our host kindly checked in with us several times."
Austin B. 2-night trip
Posted 3 hours ago
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
90
Accommodation
38 Holiday Homes
Lowest Price
AU$242
Highest Price
AU$634