Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Superhost
A spacious living room features a light-colored sofa and two matching armchairs, designed for comfort. A dark wood coffee table sits in the center, accompanied by two cups and a decorative fruit bowl. Natural light streams through the windows, highlighting the patterned area rug.
Flat in Old West End
4.94 out of 5 average rating, 180 reviews

Downtown Old West End-Fun central local with porch

This apt. is one of my favorite spaces. We used to live here and 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, roku 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 favourite
The front of the Craftsman bungalow is framed by a large tree and a colorful ornamental tree. A stone pathway leads to the entrance, surrounded by well-maintained gardens featuring various plants and shrubs. A grassy area is visible in the foreground.
Bungalow in Richmond
4.99 out of 5 average rating, 308 reviews

Artist's Retreat Guest House

The Artist's Retreat Guest House is a two-bedroom Craftsman bungalow in the Earlham College neighborhood that welcomes adults visiting our community of Richmond, Indiana. It features a living area, a fully equipped kitchen, a library filled with art books, a garden, fine antiques, and works by regional and international artists. Sorry, but no children, pets, or smoking. We keep the house allergen-free and many of the art pieces are too fragile or heavy for the safety of children and animals.

Top guest favourite
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.
Flat in Lewisburg
4.96 out of 5 average rating, 161 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!

Superhost
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.
Flat in Old West End
4.91 out of 5 average rating, 139 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
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, 378 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!

Guest favourite
The rustic exterior of the cabin is displayed, featuring a muted blue façade adorned with a brown trim. Planters filled with vibrant flowers are positioned by the entrance, complementing the greenery surrounding the porch. An eagle figure is mounted above the door, adding character to the entrance.
Cabin in Greenville
4.78 out of 5 average rating, 118 reviews

Camp Combs Cottage

Situated in the Village of Wayne Lakes 6 miles south of Greenville, Ohio. CAMP COMBS is a RUSTIC two bedroom cozy summer fish camp built in 1940 with updates. Electic controlled fireplace if there is a chill in the air. Property has fishing dock, canoe, row boat and connects to swimming area on Lake Algonquin. Unfortunately, it is NOT pet friendly. WiFi is best on front inside porch; water heater is small with good pressure. Peace, quiet and comfort for a short break, week or longer stay!

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.
Flat in Richmond
4.92 out of 5 average rating, 550 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 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.
Flat 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 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
4.95 out of 5 average rating, 153 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.
Flat in Greenville
4.96 out of 5 average rating, 198 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.

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.
Flat in Greens Fork
4.92 out of 5 average rating, 209 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.

Superhost
The pool area is surrounded by lush greenery and mature trees. A paved walkway leads to a clear, inviting pool, with a wooden pavilion nearby offering shaded outdoor seating. Potted plants add a touch of nature throughout the space, creating a serene atmosphere.
Cabin in Richmond
4.89 out of 5 average rating, 345 reviews

Cozy cabin w/ pool, hot tub, gazebo & gardens

Our original log cabin with private pool (open Memorial Day-Oct. 1), hot tub and gardens provides the perfect get away! Located on Quaker Hill right next to a retreat center, you’ll have access to trails leading to a beautiful waterfall. The Historic Downtown and Depot Districts are both just a mile away or you can visit Earlham College or explore the Antique Alley nearby.

Popular amenities for Winchester holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Randolph County
  5. Winchester