Holiday houses 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, 217 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

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 Old West End
4.91 out of 5 average rating, 154 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.

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, 199 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, 116 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 historic Queen Anne Victorian home is set amid lush greenery. The distinctive peaked red roof complements the white exterior, while large windows reflect the surrounding trees. A welcoming front porch leads to a landscaped lawn filled with grass and ornamental plants.
Guest suite in Muncie
4.97 out of 5 average rating, 427 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.
Apartment in Richmond
4.91 out of 5 average rating, 117 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
A central brick fireplace is framed by wood paneling, providing a cozy focal point. A rustic chair with a woven back is positioned beside the fireplace, enhancing the warm atmosphere. Rich hardwood flooring complements an area rug with intricate patterns, contributing to the inviting environment.
Apartment in Richmond
4.92 out of 5 average rating, 589 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.

Superhost
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.
Guesthouse in Eaton
4.87 out of 5 average rating, 361 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.

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.
Guesthouse 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.
Apartment in Greenville
4.96 out of 5 average rating, 220 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