Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A cozy sleeping area is defined by a soft white bed adorned with decorative pillows. Warm light is provided by unique hanging fixtures. A wooden table displays an arrangement of fruits and snacks alongside elegant candle holders, creating a welcoming and intimate setting.
Tower in Pleasant Hill
4.9 out of 5 average rating, 225 reviews

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

Top guest favourite
Guest suite in Muncie
4.97 out of 5 average rating, 450 reviews

The Eagle’s Nest | Historic Riverfront Retreat

Experience The Eagle's Nest, a private two-bedroom suite in The Whiteley House, an 1892 Queen Anne Victorian overlooking the White River. Enjoy a private entrance, off-street parking, full kitchen, spacious living area, and peaceful treetop views. Walk to Minnetrista, the Cardinal Greenway, and downtown, with Ball State just minutes away. Whether visiting for work, family, or a weekend escape, enjoy historic character paired with modern comfort in one of Muncie's most distinctive stays.

Guest favourite
A spacious living room is enhanced by green walls and natural light from large windows. Comfortable seating is arranged around a rustic coffee table, with a media console displaying a television. A decorative rug adds warmth to the polished wooden floor.
Cottage in Richmond
4.95 out of 5 average rating, 532 reviews

The Cottage on Abington Pike - Earlham College

Charming private cottage (home) on the West edge of Richmond within walking distance to Earlham College. This updated Three bedroom home has one custom full bath (w/Tub) & one half bath. The kitchen has been updated and is on the lower level. Great location. Wooded private rear yard with covered patio. Cardinal Greenway, Gorge Trail all of Richmond nearby. Fast Wi-Fi. Large Living room & Game room w/Pinball & Multi-cade. Outside quiet 10:00PM. Parties not allowed. 2 Tvs.

Guest favourite
A welcoming outdoor seating area is showcased with a comfortable armchair positioned next to a small wooden dining table. Potted plants add a touch of greenery, while decorative string lights overhead create a cozy ambiance. A white fence provides privacy.
Apartment in Hagerstown
4.89 out of 5 average rating, 146 reviews

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

Have fun with the whole family at this stylish place. Whether you are looking to visit family in the area or just wanting a small-town vibe to escape to, my welcoming apartment has everything you need. The unit comes with AC, Wi-Fi, Netflix, a private bathroom, and a fully stocked kitchen. Located in the heart of Hagerstown, the unit is blocks away from the local shops and restaurants on Main Street. My adorable apartment offers a deck, grill, pull-out couch, Keurig, and more!

Top guest favourite
Tiny homes in Selma
5 out of 5 average rating, 40 reviews

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-bathroom suite 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 see bunnies, geese, goats (including our free-ranging Gertie), emu, peacocks, alpacas, chickens, guinea fowl, and a donkey.

Superhost
A spacious living area is highlighted by high, open beam ceilings and exposed brick walls. Natural light fills the room through large windows adorned with soft drapes. A chandelier hangs above, while a comfortable sofa and a round coffee table create a welcoming gathering space.
Loft in Richmond
4.85 out of 5 average rating, 485 reviews

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.

Guest favourite
A wooden walkway leads to a rustic cabin and a shed, situated near a calm pond. The structure features a covered patio with seating, surrounded by greenery. Soft pastel colors fill the sky during twilight, enhancing the serene rural setting.
Cabin in Economy
4.93 out of 5 average rating, 162 reviews

"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.

Top guest favourite
A well-maintained exterior view of a modest structure featuring a green roof and light-colored siding. The entrance is framed by a wooden deck with a railing, accompanied by landscaped stones and decorative elements, including small sculptures and shrubs. Natural light highlights the inviting entryway.
Farm stay in Greens Fork
4.96 out of 5 average rating, 230 reviews

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.

Top guest favourite
A front porch area is visible, featuring two white wicker chairs with blue pillows positioned around a small dark table. A patterned rug lies underneath. A ceiling fan can be seen above, while greenery is present in the background, enhancing the outdoor setting.
Apartment in Greenville
4.96 out of 5 average rating, 230 reviews

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.

Top guest favourite
The living area features a spacious sectional sofa, a wooden coffee table, and two accent chairs. A television is positioned on a small stand across from the seating arrangement. Natural light enters through two windows adorned with blinds, illuminating the neutral-toned walls.
Apartment in Greens Fork
4.93 out of 5 average rating, 229 reviews

The Doctor's Inn, a newly renovated apartment.

You will have a great time staying in this newly renovated 2 bedroom, wheel chair accessible bathroom apartment. We have a spacious, open-concept kitchen and livingroom suitable for larger families or even hosting a small gathering or event. Located in the country 1/2 way between Indianapolis, IN and Dayton OH, you will find easy access to I 70. This apartment is pet friendly ($15/night) and is equipped with fenced yards for exercise.

Top guest favourite
A single-story house is surrounded by well-maintained lawns and greenery. Flowering trees with pink blossoms are present in the foreground, and a driveway leads to a garage beside the home. Large windows and a welcoming front door invite guests, complementing the open and airy atmosphere.
Guest suite in Muncie
4.96 out of 5 average rating, 124 reviews

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.

Guest favourite
A charming two-story home is set amidst a spacious grassy area, featuring a welcoming deck with outdoor seating. A fire pit is surrounded by four comfortable chairs, creating a cozy space for gatherings. Warm light glows from the windows as dusk begins to settle.
Home in Muncie
4.95 out of 5 average rating, 127 reviews

*Charming Westside Home Close to BSU & IU Health*

Your family will be close to everything when you stay at this centrally-located home. A short walk from Ball State's Campus and IU Health. Nestled in a peaceful and family friendly neighborhood. Plenty of room to stretch out in this large 4 bedroom house centered on an expansive wooded corner lot with a sea of grass and shade.

Popular amenities for Winchester vacation rentals

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  4. Randolph County
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