Winchester Holiday Rentals
Holiday Rentals in Winchester
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
lake front 2 br condo close to bsu
Quaker Hill Cottage on gated estate with fire pit & hiking trails
5 min walk to BSU Campus - Quiet Neighborhood
2 Bedroom Retreat near Earlham College in Richmond IN
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Cardinal Cottage - 2 bedroom cozy home
3 br country home close to town with hot tub
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Boho Bungalow off Main-one block from Lovely Park
Vintage Bungalow
Charming Home Close to all Richmond has to Offer! Dog-Friendly
Westcott Mansion with Pickleball Court & Huge Gazebo
La Dolce Vita
country home with hot tub close to town
Newly renovated studio in Hagerstown--Self Check-in
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
Recently remodeled Colonial-style home with room for the whole family!
Elegant House 2 min from BSU/Hospital/Downtown
!Country Home Get Away! !Private Backyard!
Other types of properties in Winchester you may be interested in
Randolph Inn and Suites
Baymont by Wyndham Richmond I-70
Comfort Suites
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester. Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester short-term rentals, that won’t be hard to do.
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