Holiday rentals in Winchester

Heated Pool Thru Oct 1 + Hot Tub & Theater

Perfect for families and groups! Hosted by Comfort Acres Vacation Rentals, enjoy pool days, movie nights in the theater, and fun evenings around the fire pit or hot tub under the stars. Minutes from downtown, restaurants, Grand Lake & Ohio’s Best Hometown attractions. ✔ Private Theater ✔ Heated Seasonal Pool (05/01 - 10/01) ✔ Hot Tub ✔ 4 Bedrooms + Kid-Friendly Loft Playroom ✔ Dog-Friendly ✔ Full Kitchen ✔ Fire Pit & Grill ✔ Hi Speed Wi-Fi & Smart TVs ✔ Free Parking Book now—or tap ❤️ to save!

Kick Cancers Ass With A Stay

Unique. For a Cause. Fun. A place where your stay truly counts! Your stay… Enjoy a night(s) away in an old grain elevator silo that now is home to a fully open concept layout with the most comfortable bed, a soaking tub of your dreams, handmade exposed copper piping & every detailed covered for the perfect getaway! The Cause… 20% of every nights stay goes to Pink Ribbon Good helping local ladies fight cancers. On Site… Coffee & Ice Cream Shop Axe Throwing Sand Volleyball Yard Games Boutiques

Rustic Lake house with HOT TUB and Pool Table

Come relax in your cozy 1978 Lake House! Conveniently located between Muncie and Hartford City-16 min. from Taylor University, 24 min. from Ball State, 10 seconds from the dock! Enjoy the outdoors-Take out the kayaks, go fishing, enjoy the lake, soak up the sights in the hot tub, then end your night with a campfire! Inside-Shoot some pool on the 1800's pool table, pull out a board game with the family, or just relax in the four-season sunroom while watching the sunset. Enjoy Lake Time!

Industrial & cozy 2 Bedroom atop a Historic Bldg.

Located on the 4th Floor of the Loft Highway Building in the heart of Richmond’s Historic Depot District. The Loft Highway houses such local businesses as Roscoe’s Coffee Bar & Tap Room, Lisa’s Cakes, Oblivion Cinema & Arts, Journey Yoga Studio, and The Art of Hair Salon and Metamorphosis Day Spa. Multiple other local restaurants and shops are just short walks away throughout the area. Each Guest receives 1 Free Drink from Roscoe’s (per night). Salon/Spa Booking info available upon request.

THE STARR LOFT Earlham, IUE, Reid, Relaxing Swing!

Second floor of an 1865 Tin shop, industrial building. High, open beam ceilings & exposed brick walls. Bathroom features a soaker tub plus a lux walk in shower. The kitchen features quartz counters, a large farmhouse sink, really nice appliances and thoughtful touches everywhere. The wifi is excellent. Have issues with stairs? This is not a good choice for you. If you're up for stairs and want a unique slice of history in a hip package then you will not be disappointed.

Wilderness Creek Farm Tiny House

Escape the hustle and bustle and discover the ultimate farm-stay experience. Perfectly sized for a solo traveler or a couple seeking a peaceful getaway, this cozy 1-bedroom, 1- bath home offers an intimate connection to the heart of the countryside. Sit on the front porch with your cup of coffee and enjoy the view of our farm animals! You will meet bunnies, geese, goats (including our free-ranging Gertie), emu, peacocks, alpacas, chickens, guinea fowl, and a donkey.

Justice Gästehaus apartment

Directly right off interstate 70 Within 5 miles of: • Earlham College Moore Museum • Reid Memorial Hospital • Short distance to Middleborough Reservoir Lake • Hayes Arboretum • Wayne County Museum (5-star Trip Advisor rating), which houses an authentic Egyptian mummy • One of the largest antique mall in the Midwest • Richmond Civic Theatre • 40-minute drive to Brookville Lake Smart TV you can sign in to with your Netflix &/or Amazon account (no cable)

"The Love Shack" Rustic Cabin Getaway

Cabin and/or camper spot, with 30 amp electric & hydrant water. Cabin has 1 full bed, bunk beds (max 4, bring your own linens, firm mattresses) equipped with AC/heat & mini fridge. Indiana's best keep secret - The Love Shack - nestled down a long lane in between 2 fields in rural Economy Indiana with pond & 3 acres to yourself. Started by my grandpa Tom Bond in 2000 and loved by all that visit. Follow us on social media. 2.5 miles to Cardinal greenway.

A country night under the stars!

Get away from it all when you stay under the stars. Join us for a peaceful country stay, close enough to drive to nearby shopping and dining, and far enough to hear the crickets and see the stars. Your cozy place will include a kitchenette, coffee pot, microwave & TV. The dining area inside or on the attached deck, full size bed & full bath with shower. Only 3.9 miles from Interstate 70. Should you choose to use 100-foot zipline to exercise your pet.

The Cottage Retreat

Whether you are looking for a place to spend some time or just passing through we think you’ll find it quite lovely here. We are just 5 mile off of I70 and centrally located among many places of interest. Go out or stay in. The outdoor living space is pretty spectacular! Private, with a hot tub, fire pit (wood provided), turf to play corn hole. Inside delivers all the comforts of home with full kitchen, laundry, workspace and cozy fireplace.

Cozy one bedroom apartment in a Century old house

This first floor one bedroom apartment is in a quiet neighborhood just 4 blocks from Wayne Hospital, 5 blocks from Darke County Fairgrounds and a short 5 minute walk to Downtown Greenville. It sleep up 4. The living room has a queen size sofa bed. IT has a TV with Spectrum streaming app. WiFi is available. It has a fully equipped kitchen with coffee maker and microwave. Other features include a washer and dryer and free street parking.

Country Side Getaway l

Need a breathe of fresh air? Come enjoy this en suite in the country, over looking 10 acres of wetlands, fields, and forests. Take a dip in the pool or a walk in the woods and remember what it is like to live slow. En suite includes living room area with kitchenette, private bathroom, queen bed, and beautiful views of the countryside.