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Holiday Homes in Winchester

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday homes

A living room with hardwood flooring, a leather sofa, a mounted TV, and a door leading to a kitchen.

1. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (46 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is €152
includes taxes & fees
27 Sept - 28 Sept
Cardinal Cottage - 2 bedroom cozy home

2. 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 €289
includes taxes & fees
27 Sept - 28 Sept
Pets Welcome! Quiet Economy Home w/ Spacious Yard
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, (18 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is €255
includes taxes & fees
26 Sept - 27 Sept
Retro Home Close to Campus
An outdoor patio with a round table and chairs, surrounded by a wooden deck and a green patterned rug.

4. first floor, 5 Min to Ball State & Hospital, great fire pit, deck ,full kitchen

first floor, 5 Min to Ball State & Hospital, great fire pit, deck ,full kitchen
Muncie
first floor, 5 Min to Ball State & Hospital, great fire pit, deck ,full kitchen
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 €223
includes taxes & fees
27 Sept - 28 Sept
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
A cozy living room with a sofa, a bench, a coffee table, and a patterned rug.

6. Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.0 out of 10, Wonderful, (19 reviews)
"The house is very clean and nicely appointed. Owner is quick to respond to messages. We would definitely stay here again."
United States
Joanne K.
The price is €174
includes taxes & fees
8 Oct - 9 Oct
Boho Bungalow off Main-one block from Lovely Park
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, (20 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is €291
includes taxes & fees
27 Sept - 28 Sept
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 €373
includes taxes & fees
27 Sept - 28 Sept
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

9. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 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 €283
includes taxes & fees
1 Oct - 2 Oct
Westcott Mansion with Pickleball Court & Huge Gazebo
A hotel room with a large bed, two bedside tables, a nightstand, a wall-mounted picture, and a window with curtains.

10. 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
Serene 3-bedroom house Cartier with AC in the Village at Ball State University
A hallway with a bench, a dresser, and a door leading to another room.

11. 5 min to Hospital Ball State, King, 2 Queen,2 twins, private fire pit, hot tub

5 min to Hospital Ball State, King, 2 Queen,2 twins, private fire pit, hot tub
Muncie
The price is €344
includes taxes & fees
27 Sept - 28 Sept
5 min to Hospital Ball State, King, 2 Queen,2 twins, private fire pit, hot tub
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

Comfort Suites Richmond East

Comfort Suites Richmond East

10/10 Excellent
"everything about this hotel was perfect. everything was clean breakfast was exceptional. would definitely stay here again."
Audrey 1-night trip
Posted 20 hours ago
Comfort Suites Richmond East

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
85
Accommodation
38 Holiday Homes
Lowest Price
€152
Highest Price
€373