Holiday rentals in Winchester

Lucky Hooks

Fishing and relaxation. Relax with the whole family at this peaceful place to stay. This cozy brand new home is on our 70 acre farm. Enjoy watching our cattle graze and beautiful views all around our pond! Yes, we are in the country but only a 10 minute drive to town. Close to Amish country, Serpent Mound, and Buzzard’s Roost! Space: We have plenty of room for you and your family! This is a spacious three bedroom home that includes a king size bed, queen size bed, and one twin size bunk bed!

Value · Family · Comfort

Southern Ohio Retreat w/ Private Hot Tub

White Oak Cottage is a charming rental set on the banks of White Oak Creek in southern Ohio. You'll find it nestled in the countryside between Georgetown and Mt. Orab, and about ten minutes from State Route 32. The cottage is equipped with the basics and a few extras to make your stay an enjoyable one. The bathroom and bedroom are thoughtfully furnished and the bedroom has a queen-sized bed. Outdoors there's a lovely deck that houses a completely private hot tub with a view of the creek.

Location · Value · Access

Welcome to Dancing Deer Acres!

Bring the family to this country haven. Enjoy 1500 sq. ft. of indoor comfort located near Amish communities and shops. New deck, summertime pool, fire pit, stocked pond and deer feeding station on 7 acres. Semi-detached house has private entrances. Host is available as needed but gives guests their privacy. Major stores are within 25 minutes. Hiking, fishing, hunting, fall festivals, Serpent Mound and beautiful views within an hour! On a paved road within 5 minutes of two major highways.

Location · Family · Bathroom

Private A-Frame on 20 Acres | Remote-Work Friendly

Guests consistently tell us the same thing: the photos don’t fully capture how peaceful it is here. Tucked among 20 private wooded acres in the rolling hills of southern Ohio, Solstice Haven is a modern A-frame retreat designed for quiet mornings, long walks through the woods, productive workdays, and evenings spent beneath the stars. Whether you’re planning a romantic getaway, a solo reset, or a week of remote work surrounded by nature, you’ll find the space to truly unplug or reconnect.

Value · Family · Condition

"Clover" 1830s Cabin on Hills Fork Farm

This reclaimed 1830s cabin is a rural escape located on a working farm. You'll have access to the guest cabin, bath house, fire pit, grounds, and - upon request - our working blacksmith shop. Spend an afternoon meandering trails on 75 acres of farmland and forest, sip tea on the porch, or take a drive through charming Amish country. There are two cabins on the property, and both can be booked together if you wish (please see listing for "Timothy" cabin).

Family · Value · Air conditioning

Minton Lodge - Relax, Rewind, Enjoy!

Privacy and peacefulness is what you'll experience at the beautiful Minton Lodge, a service offered by the Josh Minton Foundation. 4 bedroom and 2 full baths in a very remote location on a 49 acre wooded property . Wrap around porch, hot tub, fire pit, gas grill, smoker, and a wood stove in large living room. Walking trails with plenty of wildlife. Wifi, DirecTV, DVD player and two LCD TV's. 10 minutes from the Ohio River and Maysville, Kentucky.

Family · Location · Laundry

White Pine Cottage-cozy tiny home w/ earthy decor

Kick back and relax in this calm, stylish space.This 14x40 cottage is brand new with a front and back porch. The front porch is the whole length of the cabin with 4 rockers to sit in and relax. The back porch has seating that overlooks farmland and you may see an occasional deer grazing in the field. There is a gas grill on the back porch as well. We have a fenced private area with a fire pit and chairs to enjoy a fire on a cool night.

Value · Family · Wifi

Lazy Spread Cabin

Forget your worries in this spacious and serene space. A long winding road will lead you to a quiet rustic secluded cabin nestled on wooded acreage in the country, where you can set aside the hustle and bustle of city life and just put your feet up and enjoy nature. Whether you want to explore natural trails, visit local Amish shops or just sit on the deck and do nothing or enjoy a soak in the Hot Tub - it is all here waiting for you.

Value · Family · Outdoor spaces

Serenity Now

Escape to this serene home in the heart of Adams County, OH Amish Community. This peaceful home is surrounded by 2.5 acres of lush wooded land and an abundance of wildlife. Perfect for couples, families or solo travelers seeking a charming retreat. Sit by the fire-pit and listen to the Amish buggies trotting by, shop at local Amish businesses, spend the day hiking or visiting local state parks and lakes.

Value · Location · Check-in

Country Cabin (Pine Valley Cabins)

We offer 720sq ft. of space for the whole family. 1 or 2 bedrooms with extra cots, walk in closets, stand up shower, washer/dryer, fridge, microwave, full stove/oven, coffee pot, cooking pots, dish-ware, a/c / heat in each room. Eat in kitchen with Amish made dinette set. Couch that folds out to make bed. Outside smoke-less fire pit with grill option. No pets Unless approved

Location · Family · Kitchen

Amish-built cabin on pond/amazing view!

Private, secluded cabin awaits. Enjoy 80 acres of fields, forests, and pond. Amish-built cabin with beautiful décor, full bath, loft bedroom, full kitchen with island. Watch the sunset off the back deck. Owner is easily accessible in case you need anything. If you are looking for peace and quiet with spectacular views...welcome home. (Pet friendly)

Value · Family · Indoor spaces

Bradford Paradise

Welcome to Bradford Paradise. This charming 3-bedroom, 2-bathroom home in Sardinia, OH. Ideal for families, business travelers, or a small groups of friends, this fully furnished home offers a comfortable and relaxing stay. With a spacious layout and modern amenities, it’s designed to make your visit as relaxing and enjoyable as possible.

Value · Location · TV