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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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Top guest favourite
A spacious living room features two dark blue sofas facing each other, centered around a wooden coffee table. A large flat-screen TV is mounted on the wall above an electric fireplace. Soft lighting from lamps accentuates the cozy atmosphere, complemented by a colorful area rug.
Home in Muncie
4.97 out of 5 average rating, 126 reviews

Farm Themed w/2 Game Rooms & HOT TUB -2 min to BSU

Come and enjoy our newly renovated Tri-Level "Farmhouse" Home! -Large and relaxing Hot tub, with ample outdoor seating, fully fenced in back yard -3 KING beds, and 2 Twins between 4 bedrooms Lots of activities-Pool table, Chess table, Golden Tee Classic, Mrs. Pacman, Ping Pong, Foosball, and board games -Accommodates up to 8 people - Children and pet friendly -Located in a quiet, safe neighborhood - 4 min to Ball State, 7 Min to Downtown Muncie -Roku Smart TV's in each room Relax, and have fun!

Top guest favourite
Cabin in Celina
4.97 out of 5 average rating, 152 reviews

Heated Pool + Hot Tub | Rustic Log Cabin

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!

Top guest favourite
A welcoming deck is highlighted with various seating arrangements, including two chairs and a small table. Lush greenery surrounds the tranquil lake, where well-maintained paths and fire pits are visible along the water's edge, providing a serene outdoor setting.
Home in Greenville
4.92 out of 5 average rating, 212 reviews

18 LakeS, Dead End Lane, DogS, SpaciouS, 1 nightS

Nestled within the serene surroundings of a picturesque lake community, this delightful lake house offers a charming blend of comfort & convenience. Boasting 3 bed,2 baths, a spacious living room & large kitchen. Outdoors you'll find a dock, paddle boat,& 18 lakes to enjoy. Located as the 1st house of 3 on a quiet dead end. Perfect for those looking to enjoy peaceful evenings on the lake. We are happy to welcome dogs for a fee with your stay. 1 night Stays upon REQUEST! 2 fish passes included.

Guest favourite
The living room features a green velvet sofa, adorned with decorative cushions. A wall showcases various pieces of local artwork, providing a pop of color. A television sits on a simple stand, with a coffee table positioned in front, enhancing the cozy seating area.
Apartment in Muncie
4.9 out of 5 average rating, 176 reviews

Cute Studio in Old West End

Enjoy a budget-friendly experience at this cozy apartment in Muncie's Old West End neighborhood. Close to downtown hotspots and a short hop to BSU/hospital. Perfect for 1-2 guests. Newly renovated and stylish; all art in the apartment is by local artists. *Please note*, there are no exceptions to the “nonrefundable” option if you choose it. Please research our neighborhood before booking - our prices reflect our location in a diverse, populated urban neighborhood that is being revitalized.

Top guest favourite
The exterior of a two-story Techbuilt home is surrounded by lush greenery, showcasing large windows that invite natural light. A mature tree stands nearby, providing shade to the well-kept yard. The cedar siding highlights the home's mid-century architectural style.
Apartment in Richmond
4.93 out of 5 average rating, 615 reviews

Private Apartment-800sq ft Next to Earlham College

Upper level separate apartment. Short stroll to Earlham College campus, ball fields, tennis courts, stables and Athletic Center. 5 houses up from the President's house. Windows galore offer natural lighting. Quiet neighborhood. Hardwood floors give that cozy feeling. Guaranteed clean and private. Well-behaved pets welcome. Breakfast not included. Coffee, tea, microwave, toaster oven and refrigerator in apartment. Host lives in lower apartment with dog and 2 cats. Chickens in the back yard.

Guest favourite
A glass vase with delicate yellow branches is centered on a wooden dining table. The background reveals a cozy living area with vintage seating and a television on a brick wall, while a glimpse of a bedroom can be seen through an open door.
Apartment in Richmond
4.9 out of 5 average rating, 130 reviews

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.

Top guest favourite
Guest suite in Muncie
4.97 out of 5 average rating, 459 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.

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, 245 reviews

A peaceful night under the stars in the country.

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 or a path to walk around our field.

Top 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, 540 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.

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, 235 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
The exterior of the house is framed by lush greenery and well-manicured shrubs. A welcoming front porch is highlighted by white railings and a green roof. The landscaping is complemented by a smooth pathway leading to the entrance.
Home in Richmond
4.98 out of 5 average rating, 132 reviews

Yellow House on the Hill Country Retreat

This quiet oasis in the country is perfect for family gatherings, small events, or a productive place to focus on work. The house is perched on a hill outside of town, providing a scenic overlook of rolling hills. Enjoy the sunrise on the front porch, and watch the sunset on the back patio. There is year round fun with sledding in the winter and barbecuing in the summer.

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.

Popular amenities for Winchester vacation rentals