Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
The loft features exposed red brick walls and a raftered ceiling, creating a historic character. A spacious bed with a white coverlet is positioned beside two large windows with light curtains. A wooden table and chairs are situated in a cozy corner, complemented by decorative lighting.
Apartment in Lewisburg
4.96 out of 5 average rating, 166 reviews

Leader Loft

Conveniently located less than a mile from I-70 exit 14, on State Highway 503. This loft is perfect for any stay length for every occasion, and with the electronic door lock system it is perfect for a last minute stop as you’re traveling down the interstate. The Loft shares our building with Flour Bakery, coffee and gift shop, and is a minute's walk from a delicious bistro, antique shops, other gift shops, the library and hardware store. Come explore all that our quaint village has to offer!

Guest favorite
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 Old West End
4.91 out of 5 average rating, 141 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 favorite
A serene bedroom features a spacious bed with soft linens and decorative pillows. A reading chair is positioned next to large windows, allowing natural light to illuminate the room. A decorative sign and plants add subtle character to the calming atmosphere.
Guest suite in Muncie
4.97 out of 5 average rating, 383 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Top guest favorite
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
4.92 out of 5 average rating, 552 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.

Top guest favorite
A comfortable living area is highlighted by a caramel-colored sofa and two armchairs with decorative cushions. A wooden coffee table sits in the center, complemented by a woven basket and plants. Art prints hang on the wall, and a large TV is mounted nearby.
Home in New Castle
4.99 out of 5 average rating, 207 reviews

Entire Home with Modern Conveniences - New Castle

This home has been equipped with everything you need for a relaxing stay. Unwind in the evening while watching your 65” TV. The updated kitchen offers plenty of space for cooking dinner.The first bedroom features a King size bed and room darkening window treatments. The second bedroom offers a designated office space w/ high speed internet and a trundle bed. To start your day well, the bonus room offers a coffee bar with Nespresso and wellness area complete with treadmill and yoga space.

Guest favorite
A cozy living room features a dark couch adorned with decorative cushions, paired with a patterned loveseat. A coffee table sits at the center, with two cups resting atop it. Natural light enters through two windows, framed by soft curtains, illuminating the wooden floor.
Apartment in Old West End
4.91 out of 5 average rating, 190 reviews

Central Location. Very comfy & clean with view.

This lovely little retreat will not disappoint. I think you will find it to be a relaxing and comfortable place to spend your time in Muncie. We've provided the basics so that it can be your home away from home: fully functioning kitchen, coffee options, hi speed internet, towels, shampoo, conditioner, soaps, bedding, xfinity flex with tv, and board games. 1/2 mile to shops & dining or a walk along the river, 1 mile to BSU. Close the day grilling out while you watch the gorgeous sunset.

Top guest favorite
A spacious home is presented in a scenic outdoor setting, with a charming garden of vibrant flowers in the foreground. The building features a combination of textured stone and siding, framed by a serene sunset sky that enhances the peaceful ambiance.
Guesthouse in Versailles
4.97 out of 5 average rating, 260 reviews

French B&B - Lower Level Apt w/ 2 bedrooms

The French Bed & Breakfast is nestled in the charming town of Frenchtown, Ohio. This B&B has been operating since 1999 and has accommodated many guests coming to visit Darke County. Lower level of our house - it has spacious and quaint accommodations for a reasonable rate. Included: Continental Breakfast, kitchen, great room & patio. Guest rooms on lower level: 2 bedrooms - can be rented individually or as a 2 bdrm apartment (pricing varies based on events - min $75 ea bdrm).

Top guest favorite
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
4.96 out of 5 average rating, 492 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 favorite
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
4.88 out of 5 average rating, 128 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 favorite
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
4.95 out of 5 average rating, 158 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 favorite
A spacious living area features warm wooden flooring and a cozy seating arrangement. A television is positioned on a dark wooden console, with a rocking chair nearby. A window seat with soft cushions offers additional seating, while framed photographs decorate the walls.
Apartment in Pendleton
4.98 out of 5 average rating, 317 reviews

Studio by Falls Park

Welcome to the Studio by Falls Park. This is a family-friendly studio apartment with a separate entrance. You are within walking distance to several good restaurants and the local drinking hole (The Wine Stable), Falls Park, walking trails. Located 10 minutes off I-69, and 20 minutes North of Indianapolis. Harrah’s casino is 15 minutes North on I-69. Studio has shower/bath, 1 queen bed, a full size futon, queen size blowup mattress and kitchen.

Top guest favorite
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
4.97 out of 5 average rating, 201 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.

Popular amenities for Winchester vacation rentals

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