Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Top 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, 215 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

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
4.92 out of 5 average rating, 188 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.

Guest favourite
An open-concept living space features a dining table set for four, with polished plates and glasses. A cozy sofa is adjacent to the fireplace, and the kitchen area includes wooden cabinetry and modern appliances. Natural light filters in through large windows, accentuating the wood paneling.
Home in Hartford City
4.92 out of 5 average rating, 198 reviews

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!

Top guest favourite
A spacious front porch features four cushioned chairs and two small tables, inviting relaxation. Lush plants and hanging flower baskets enhance the area, while the entrance includes a handrail leading to the porch. Soft, filtered light casts gentle shadows, creating a welcoming atmosphere.
Home in Richmond
4.94 out of 5 average rating, 115 reviews

Cozy 3BRw/porch kids OK, no pets, near EC-IUE-Reid

This private, spacious, two-story home was built in 1918. Past guests have loved the cozy gas fireplace and lovely front porch. It sleeps up to 6 in 3 upstairs bedrooms; with half bath on main floor, full bath upstairs. We do not allow pets. The place is kid-friendly, across from a wooded city park with rentable shelters, a playground and a basketball court. In a quiet residential area 3 blocks from Earlham College, 3.7 miles from Reid Hospital/IU East, 2.5 miles from Wayne County Fairground.

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, 426 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
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.
Flat in Richmond
4.91 out of 5 average rating, 116 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.

Guest favourite
A timber-framed home is set within a lush landscape, featuring a tranquil swimming pool surrounded by vibrant shrubs and greenery. Two lounge chairs are positioned near the pool, while trees provide shade. The exterior of the home showcases a green metal roof against a clear blue sky.
Guest house in Eaton
4.88 out of 5 average rating, 360 reviews

Cozy Pool House in the Country on 25 acres

The pool house is close to Muncie, Indiana and Ball State and Taylor Universities. We are also only about 5 miles from Barn on Boundary and have hosted several wedding parties. You’ll love our place because of the location, it feels like a secluded lodge. The timber frame structure is unique and has all the comforts of home. It has a very open floor plan and is very quiet and peaceful. It is good for couples, solo adventurers, families (with kids), big groups, and furry friends (dogs).

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
4.91 out of 5 average rating, 197 reviews

18 LakeS, Dead End Lane, DogS, SpaciouS, Ice Fish

Nestled within the serene surroundings of a picturesque lake community, this delightful lake house offers a charming blend of comfort and convenience. Boasting 3 bed,2 baths, a spacious living room and 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. 2 guest fishing passes are INCLUDED with your stay.

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, 516 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
The dining area features a wooden table surrounded by six chairs, adorned with floral placemats. A potted plant sits at the center of the table. Natural light filters in through a window beside a decorative shelf, enhancing the welcoming setting.
Guest house in Muncie
4.87 out of 5 average rating, 364 reviews

Carriage House Loft Apartment

Welcome to our recently remodeled Carriage House Loft Apartment! We're happy to share our simple, comfortable, cozy space with you. Refurbished original hard wood floors with updated kitchenette area and bathroom. Charming and convenient, walk two blocks to the Cardinal Greenway & White River trails, and one mile to downtown Muncie! Perfect for 2 - 4 people, or a family with an infant/toddler. Enjoy self-check-in, privacy, & dedicated parking steps from the entrance.

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, 204 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, 218 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 holiday rentals

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