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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchester holiday rentals

Interior

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is HK$847
HK$2,561 total
includes taxes & fees
30 Sept - 1 Oct
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Living area

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 HK$604
HK$2,486 total
includes taxes & fees
30 Sept - 1 Oct
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A kitchen with wooden cabinets, a stainless steel stove, and a refrigerator.

3. New Hagerstown Apartment - Self Check-in. Sleeps 4+

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (27 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
The price is HK$501
HK$1,132 total
includes taxes & fees
5 Oct - 6 Oct
New Hagerstown Apartment - Self Check-in. Sleeps 4+
A modern kitchen with stainless steel appliances, wooden cabinets, and a white tiled backsplash.

4. 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, (18 reviews)
"This is a darling place in a wonderful town. It met all of our needs and we'll definitely stay here again."
United States
Tamera
The price is HK$558
HK$1,284 total
includes taxes & fees
5 Oct - 6 Oct
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
A living room with hardwood flooring, a leather sofa, a mounted TV, and a door leading to a kitchen.

5. 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 HK$706
HK$1,318 total
includes taxes & fees
30 Sept - 1 Oct
Cardinal Cottage - 2 bedroom cozy home
A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

6. 'Downtown Delight' w/ Patio! 1 Mi to Ball State

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
9.8 out of 10, Exceptional, (28 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is HK$863
HK$2,565 total
includes taxes & fees
30 Sept - 1 Oct
'Downtown Delight' w/ Patio! 1 Mi to Ball State
A modern living room with a sofa, armchair, and a white spiral staircase.

7. Quaker Hill Cottage on gated estate with fire pit & hiking trails

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.4 out of 10, Exceptional, (36 reviews)
"Very nice place to spend the night while passing through on Route 70. The Thistlethwaite Falls are only minutes away and were a perfect evening activity after driving all day."
United States
Jon and Keri C.
The price is HK$902
HK$1,713 total
includes taxes & fees
4 Oct - 5 Oct
Quaker Hill Cottage on gated estate with fire pit & hiking trails
A hotel lobby with a reception desk, a dining area with round tables and chairs, a kitchen area, and a window with a view.

8. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (152 reviews)
"The staff were friendly and helpful throughout our stay. It felt welcoming right away."
United States
Anonymous traveller
The price is HK$475
HK$605 total
includes taxes & fees
25 Oct - 26 Oct
King Bed Non-Smoking
A hotel room with two beds, a small table, a mirror, and a bathroom with a sink and toilet.

9. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (116 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveller
The price is HK$509
HK$650 total
includes taxes & fees
28 Oct - 29 Oct
2 Queen Beds Non-Smoking
Start your day at the coffee station — Keurig, drip, or French press featuring local coffee (regular and decaf), tea, creamer, sugar and sweetener. We take coffee very seriously!

10. 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, (8 reviews)
"The property was absolutely beautiful, just as pictured!!! it’s a must stay."
United States
Simonne S.
The price is HK$1,161
HK$2,091 total
includes taxes & fees
25 Oct - 26 Oct
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
A dining area with a table set for four, chairs, and a patterned wallpaper.

11. 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 HK$1,059
HK$2,240 total
includes taxes & fees
30 Sept - 1 Oct
Retro Home Close to Campus
A cozy living room with a sofa, a bench, a coffee table, and a patterned rug.

12. 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 HK$847
HK$1,520 total
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.

13. 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 HK$1,235
HK$2,447 total
includes taxes & fees
30 Sept - 1 Oct
Charming Home! Prime Location! Dog-Friendly!
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with a view.

14. 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 HK$1,247
HK$1,880 total
includes taxes & fees
30 Sept - 1 Oct
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.

15. 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 HK$1,294
HK$2,460 total
includes taxes & fees
1 Oct - 2 Oct
Westcott Mansion with Pickleball Court & Huge Gazebo
A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

16. 'downtown Delight' w/ Patio! 1 Mi to Ball State

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
The price is HK$1,177
HK$2,517 total
includes taxes & fees
30 Sept - 1 Oct
'downtown Delight' w/ Patio! 1 Mi to Ball State
Exterior

17. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
10.0 out of 10, Exceptional, (1 review)
"Stay was awesome. House was so clean and host was awesome."
United States
Sharon C.
The price is HK$902
HK$1,625 total
includes taxes & fees
26 Oct - 27 Oct
Cozy 2-bedroom next to Cardinal Greenway Trail
A hotel room with two beds, a nightstand with a lamp, and a wall-mounted telephone.

18. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$461
HK$510 total
includes taxes & fees
6 Oct - 7 Oct
2 Queen Beds | Non-Smoking
A bedroom with a bed, a dresser, a television, and a chair.

19. 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
5 min to Hospital Ball State, King, 2 Queen,2 twins, private fire pit, hot tub
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

20. 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 HK$3,294
HK$3,514 total
includes taxes & fees
11 Oct - 12 Oct
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
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

Motel 6 Richmond, IN

Motel 6 Richmond, IN

10/10 Excellent
"Clean. Quite. Perfect"
Tessa 1-night trip
Posted 4 hours ago
Motel 6 Richmond, IN

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its golf courses.

What are some of the best holiday rentals that Winchester has to offer?

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA: This highly rated holiday home rental in Winchester is located in a rural location, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Speedway and Winchester Golf Club are other places to visit while you're in town.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family gatherings.