Search Holiday Rentals in Winchester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Winchester

Fridge, microwave, oven, stovetop
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
10.0 out of 10, Exceptional, (159)
"Overall a perfect Bachelor Party for us 25 - 55 year old guys! Basketball, Firepit, cooking out, Pool and more! Highly recommend if you plan for a one stop place of bringing your food, booze, and fun!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Exterior
lake front 2 br condo close to bsu
9.2 out of 10, Wonderful, (24)
"Booked the condo for a 2 night weekend stay due to a volleyball tournament in yorktown. The place was like a mini vacation, the lake view was beautiful, the weather was perfect and I was able to grill some food in the patio and soak in the hot tub before bed. If my daughter has any more volleyball tournaments nearby I will 100% look for this listing first. The condo had all the necessities and the location was perfect. Volleyball is stressful and it was so nice to have this place to go to after...
lake front 2 br condo close to bsu
Exterior
Quaker Hill Cottage on gated estate with fire pit & hiking trails
10.0 out of 10, Exceptional, (11)
"This property is beautiful and the house was very clean. The only thing I recommend is for it listed as handicap not friendly. I could not go up and down the stairs because I have some severe back problems. The stairs are steep and winding. However because there are 2 bedrooms and everything I need on the floor we entered, I had no problem staying there. It was a very nice place and we enjoyed it very much. The location is convenient to downtown Richmond. We had no problem finding it. The...
The price is £178
includes taxes & fees
23 May - 24 May
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
5 min walk to BSU Campus - Quiet Neighborhood
10.0 out of 10, Exceptional, (43)
"Our family came down to celebrate senior weekend for Ball State baseball. This house was perfect for our family and loved the quiet neighborhood. I just wish we would’ve found it sooner."
5 min walk to BSU Campus - Quiet Neighborhood
Outdoor dining
2 Bedroom Retreat near Earlham College in Richmond IN
10.0 out of 10, Exceptional, (18)
"After you park you enter a little Oasis right in town. This place is stunning! Beds and couches are comfortable! Listening to the tiny waterfall in this wonderful backyard setting is a must! Landscape is immaculate. You almost feel secluded like you are out in the woods, because of all the trees surrounding majority of the place. Best candle company(Warm Glow) shop 15 min drive."
2 Bedroom Retreat near Earlham College in Richmond IN
Fridge, microwave, oven, stovetop
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
The price is £130
includes taxes & fees
27 May - 28 May
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Exterior
Cardinal Cottage - 2 bedroom cozy home
10.0 out of 10, Exceptional, (1)
"Clean and comfortable two bedroom"
The price is £144
includes taxes & fees
27 May - 28 May
Cardinal Cottage - 2 bedroom cozy home
Fridge, microwave, oven, stovetop
3 br country home close to town with hot tub
9.6 out of 10, Exceptional, (15)
"Cute property. Enjoyed our time in Indiana. Maybe needs new mattresses. I have never stayed in a vrbo so wasn't sure if i needed to wash towels or sheets. 🤔 When i booked the place it said we would receive email from Host of instructions, we never received an email. Overall, nice older home."
3 br country home close to town with hot tub
Living area | Smart TV, fireplace, DVD player
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
10.0 out of 10, Exceptional, (10)
"Fishing was amazing and lots of space for our kids to run and play!"
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Private kitchen
Boho Bungalow off Main-one block from Lovely Park
9.2 out of 10, Wonderful, (5)
"We liked the cleanliness of the property. There is also plenty of things to do and great places to eat with in a short distance of the property"
The price is £104
includes taxes & fees
23 May - 24 May
Boho Bungalow off Main-one block from Lovely Park
Fridge, microwave, oven, stovetop
Vintage Bungalow
The price is £354
includes taxes & fees
22 Jun - 23 Jun
Vintage Bungalow
Property grounds
Charming Home Close to all Richmond has to Offer! Dog-Friendly
The price is £281
includes taxes & fees
28 May - 29 May
Charming Home Close to all Richmond has to Offer! Dog-Friendly
8 bedrooms, WiFi, bed sheets
Westcott Mansion with Pickleball Court & Huge Gazebo
9.8 out of 10, Exceptional, (18)
"It was a great place for our group to gather to watch the eclipse, and then visit with each other afterwards. Very historic house with potential to be even more grand if renovations continue. The gazebo is nice. The yard would be even better with a garden or flowering trees. We enjoyed exploring the house. So much room!"
The price is £246
includes taxes & fees
28 May - 29 May
Westcott Mansion with Pickleball Court & Huge Gazebo
Private kitchen
La Dolce Vita
2.0 out of 10, (2)
"The pictures uploaded are either very old, or doctored. Bed sheets had stains on them with black light. Cameras installed throughout the inside of the home. No running water when we arrived. We checked into a motel, and then owner tried to charge me $2000.00 for "water damage", when there was no running water and we never stayed."
The price is £204
includes taxes & fees
23 May - 24 May
La Dolce Vita
Fridge, microwave, oven, stovetop
country home with hot tub close to town
9.0 out of 10, Wonderful, (26)
"The home was perfectly located for watching totality in 2024. Just far enough out of town to have a country feel, but close enough to Muncie to make shopping and dining convenient."
country home with hot tub close to town
Fridge, microwave, oven, stovetop
Newly renovated studio in Hagerstown--Self Check-in
10.0 out of 10, Exceptional, (22)
"It looks just like the pictures. Very clean. The parking was very convenient. I would absolutely stay here again."
The price is £122
includes taxes & fees
5 Jun - 6 Jun
Newly renovated studio in Hagerstown--Self Check-in
Fridge, microwave, stovetop, dishwasher
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
10.0 out of 10, Exceptional, (8)
"Quiet, clean and comfy!"
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
Exterior
Recently remodeled Colonial-style home with room for the whole family!
10.0 out of 10, Exceptional, (20)
"This home is in a cute quiet neighborhood and was perfectly appointed. While we didn’t have a chance to use the backyard fire pit area we sure wanted to. We appreciated the coffee and basket of snacks provided. This was the perfect place for us and only 35 minutes from Oxford."
Recently remodeled Colonial-style home with room for the whole family!
Fridge, microwave, oven, stovetop
Elegant House 2 min from BSU/Hospital/Downtown
10.0 out of 10, Exceptional, (1)
"Lovely, well equipped, two story house in calm area near BSU; host was very responsive to minor glitch in door lock; property and house were very nicely decorated and maintained; kitchen was well equipped; linens were fresh; even a Brita pitcher was available to help with Muncie's known water "flavor" Highly recommend property to all unless steep stairs to bedrooms would pose an issue."
The price is £350
includes taxes & fees
27 May - 28 May
Elegant House 2 min from BSU/Hospital/Downtown
Fridge, microwave, oven, stovetop
!Country Home Get Away! !Private Backyard!
10.0 out of 10, Exceptional, (7)
"Property is as described. Super quiet, perfect for a place to stay while in the area working."
!Country Home Get Away! !Private Backyard!
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Golf
Randolph Inn and Suites
2.5 star property
9.0 out of 10, Wonderful, (183)
"Super friendly and clean!!!"
The price is £132
includes taxes & fees
26 May - 27 May
Randolph Inn and Suites
Lobby
Baymont by Wyndham Richmond I-70
2.5 star property
8.0 out of 10, Very good, (894)
"Clean and quiet. "
The price is £63
includes taxes & fees
16 Jun - 17 Jun
Baymont by Wyndham Richmond I-70
Exterior
Comfort Suites
2.5 star property
9.4 out of 10, Exceptional, (234)
"Very friendly staff and a very clean place to stay. Rooms are large and spacious. Pool was a little on the cooler side but nice non the less. Breakfast was average, would like to see a juice machine. They are working on an outside patio space which will be nice. Would stay here again. Rings and wings, McDonald's and Culver's all are walkable from the hotel."
The price is £84
includes taxes & fees
16 Jun - 17 Jun
Comfort Suites
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.

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, apart-hotels, 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 £104 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?

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 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 garden, a pool table and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Winchester?

Expedia has 3 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

While you're exploring the area, Prairie Creek Reservoir and Campground and Summit Lake State Park are a couple of picturesque spots to get outside and enjoy nature. Winchester Speedway and Historic Shopping & Dining District of Winchester, Indiana 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.

Recent reviews of Winchester properties
Expedia verified reviews

Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center

5/5 Excellent
"Room was not cleaned as well as I would have expected for a Mariott. I loved the location and everything else was very clean. The staff was very kind. "
A verified traveller stayed at Courtyard Muncie at Horizon Convention Center
Posted 1 day ago
Courtyard Muncie at Horizon Convention Center