Default HTG hotel image

Winchester Holiday 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
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 rentals

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 NZ$567
includes taxes & fees
30 Sept - 1 Oct
Pets Welcome! Quiet Economy Home w/ Spacious Yard

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is NZ$570
includes taxes & fees
27 Sept - 28 Sept
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.

3. 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 NZ$293
includes taxes & fees
28 Sept - 29 Sept
Cardinal Cottage - 2 bedroom cozy home
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a microwave.

4. 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 NZ$253
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.

5. 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 NZ$273
includes taxes & fees
28 Sept - 29 Sept
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
A modern living room with a sofa, armchair, and a white spiral staircase.

6. 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 NZ$383
includes taxes & fees
20 Oct - 21 Oct
Quaker Hill Cottage on gated estate with fire pit & hiking trails
A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

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

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
10.0 out of 10, Exceptional, (27 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is NZ$589
includes taxes & fees
24 Sept - 25 Sept
'Downtown Delight' w/ Patio! 1 Mi to Ball State
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 NZ$136
includes taxes & fees
19 Oct - 20 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, (115 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveller
The price is NZ$146
includes taxes & fees
3 Oct - 4 Oct
2 Queen Beds Non-Smoking
A dining area with a table set for four, chairs, and a patterned wallpaper.

10. 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 NZ$520
includes taxes & fees
27 Sept - 28 Sept
Retro Home Close to Campus

11. 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 NZ$385
includes taxes & fees
20 Oct - 21 Oct
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

12. 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 NZ$559
includes taxes & fees
27 Sept - 28 Sept
Charming Home! Prime Location! Dog-Friendly!
A living room with a brick wall, wooden flooring, a sofa, a coffee table, a TV, and a staircase leading to another room.

13. '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 NZ$560
includes taxes & fees
24 Sept - 25 Sept
'downtown Delight' w/ Patio! 1 Mi to Ball State
A reception area with a reception desk, a clock on the wall, and a bulletin board with pictures.

14. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
The price is NZ$119
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Non-Smoking
An outdoor patio with a round table and chairs, surrounded by a wooden deck and a green patterned rug.

15. 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 cozy living room with a sofa, a bench, a coffee table, and a patterned rug.

16. 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 NZ$339
includes taxes & fees
8 Oct - 9 Oct
Boho Bungalow off Main-one block from Lovely Park
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with a view.

17. 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 NZ$423
includes taxes & fees
2 Oct - 3 Oct
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
A modern lounge area with leather seating, a wooden bar, and a large flat-screen TV.

18. 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 NZ$747
includes taxes & fees
24 Sept - 25 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.

19. 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 NZ$564
includes taxes & fees
1 Oct - 2 Oct
Westcott Mansion with Pickleball Court & Huge Gazebo
A beige leather sofa with multiple cushions, a patterned rug, and a wooden floor.

20. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
The price is NZ$366
includes taxes & fees
18 Oct - 19 Oct
Cozy 2-bedroom next to Cardinal Greenway Trail
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

Comfort Suites Richmond East

Comfort Suites Richmond East

10/10 Excellent
"Property was amazing, very clean and would definitely stay their again."
Ashley 1-night trip
Posted 19 hours ago
Comfort Suites Richmond East

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as NZ$136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Mansfield Park 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.