Holiday rentals in Winchester

Spacious & Rustic Gem: Movie Theater + Heated Pool

Escape to Brown Bear Log Cabin—your peaceful retreat in the woods. It promises a relaxing retreat just a few minutes from local restaurants, shops, breweries, exciting attractions, and natural landmarks. ✔ Movie Theater ✔ Heated Seasonal Pool (Open Late May to Late Sept) ✔ Loft Playroom ✔ Living Area ✔ Fully Equipped Kitchen ✔ Workspace ✔ Yard (Fire Pit, BBQ, Dining, Lounge) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Bike Path (0.25 miles away) ✔ 4 Comfortable Bedrooms Learn more below!

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.

Cute Studio in Old West End

Enjoy a cozy experience at this centrally-located 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. Also, please research our neighborhood before booking. This is a populated urban location in a neighborhood that is in the process of revitalization.

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!

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.

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.

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!

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.

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.