
Holiday houses in Winchester
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Top-rated holiday rentals in Winchester
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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!
4.97 out of 5 average rating, 127 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!
4.97 out of 5 average rating, 153 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.
4.92 out of 5 average rating, 213 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.
4.97 out of 5 average rating, 466 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.
4.96 out of 5 average rating, 246 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.
4.95 out of 5 average rating, 542 reviews
THE STARR LOFT Earlham, IUE, Reid, Relaxing Swing!
Second floor of an 1865 Tin shop, industrial building. High, open beam ceilings & exposed brick walls. Bathroom features a soaker tub plus a lux walk in shower. The kitchen features quartz counters, a large farmhouse sink, really nice appliances and thoughtful touches everywhere. The wifi is excellent. Have issues with stairs? This is not a good choice for you. If you're up for stairs and want a unique slice of history in a hip package then you will not be disappointed.
4.85 out of 5 average rating, 494 reviews
Mid-Ave House
Welcome to the Mid-Ave House, in Albany, IN! This charming 1-bedroom, 1-bathroom house has been completely updated with all the modern amenities you need for a comfortable and convenient stay. The bathroom is fully updated with a shower/tub combo, fresh towels, and toiletries. The kitchen offers you updated appliances along with complimentary coffee, tea and water bottles. Whether you're in town for an event or pleasure, the Mid-Ave House is the perfect house for you.
4.8 out of 5 average rating, 74 reviews
Wilderness Creek Farm Tiny House
Escape the hustle and bustle and discover the ultimate farm-stay experience. Perfectly sized for a solo traveler or a couple seeking a peaceful getaway, this cozy 1-bedroom, 1- bath home offers an intimate connection to the heart of the countryside. Sit on the front porch with your cup of coffee and enjoy the view of our farm animals! You will meet bunnies, geese, goats (including our free-ranging Gertie), emu, peacocks, alpacas, chickens, guinea fowl, and a donkey.
5.0 out of 5 average rating, 50 reviews
LazyDaze | 3 BR, EV Charger, 75" TV, Gigabit WiFi
Welcome to LazyDaze! Enjoy a blend of comfort and style in this modern executive retreat in Albany. This house can accommodate 6 guests within the three luxurious bedrooms. Cook in the fully-equipped kitchen, savor a coffee or tea at the coffee bar, and relax in the living room with a 75" Smart TV and blazing fast internet. Outside, unwind on the deck and charge your EV with our Level 2 charger (up to 10.1 kW, J1772). Book your stay and experience LazyDaze!
5.0 out of 5 average rating, 49 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.
4.93 out of 5 average rating, 237 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.
4.99 out of 5 average rating, 135 reviewsPopular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

4 Bedroom Home - Hot Tub - Fire Pit
4.97 out of 5 average rating, 69 reviews
Rustic Converted Barn 1- Bedroom open floor plan
4.84 out of 5 average rating, 99 reviews
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
4.96 out of 5 average rating, 57 reviews
Checkers: Vintage + Modern Charm
5.0 out of 5 average rating, 47 reviews
Quiet Home on the Lake
4.88 out of 5 average rating, 34 reviews
4bedroom 3King beds+1Twin/Deck, Movie Theater+ADU
5.0 out of 5 average rating, 42 reviews
Newly Renovated, Quiet Home for Families
5.0 out of 5 average rating, 95 reviews
Charming apartment in a quaint town. Self check-in
4.95 out of 5 average rating, 86 reviewsDestinations to explore
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