Holiday rentals in Winesburg

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Top-rated holiday rentals in Winesburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Dundee
4.98 out of 5 average rating, 327 reviews

Woodstone Cottage in the Heart of Amish Country

This quaint cottage is nestled in the rolling hills of scenic Amish Country. It's located within a mile of the historical town of Winesburg and 5 miles from Berlin and Walnut Creek. You can explore lots of Coffee Shops, Restaurants, Antique Malls and unique Boutique Shops. You will also find Breitenbach Wine Cellars in Sugarcreek and your kids will love to visit The Farm in Walnut Creek. You will also find lots of spots for hiking. At the Dundee Falls and the Wilderness center located in Wilmont

Top guest favourite
Cottage in Dundee
4.97 out of 5 average rating, 166 reviews

Pear Tree Cottage~A Step Back in Time+Mini Donkeys

Escape the bustle and noise of everyday at the Peartree Cottage in the heart of Ohio's Amish Country.The private cottage peeps out from the folds of the eastern hills of Holmes County, directly in the heart of the worlds largest Amish community.It is surrounded by stunning scenery amidst every season, most stunning in fall.Grind your own coffee with our endless supply of coffee beans.Fresh homemade maple frosted cinnamon rolls and delicious fresh baked bread will be at the cottage, just for you.

Top guest favourite
The cabin features a rustic log exterior surrounded by trees with vibrant autumn foliage. A spacious porch, equipped with multiple wooden chairs, invites relaxation. Large windows reflect natural light, enhancing the cabin's warm atmosphere, while the grassy area provides ample space for outdoor enjoyment.
Cabin in Millersburg
4.95 out of 5 average rating, 236 reviews

Mockingbird Hill Lodge

Mockingbird Hill Lodge warmly welcomes you! You may want to retreat for a time with family and friends, surrounded by nature. Or a 5 minute drive will take you to the bustle of our unique small town attractions. Return to the comfort of our 4 bedroom cabin each evening, relax in beds designed for a blissful sleep experience. However you choose , do not miss the joy of greeting the sun over coffee on the front porch swing. You can tuck away the feeling, then relive it as needed to be refreshed!

Top guest favourite
Guest house in Millersburg
4.99 out of 5 average rating, 296 reviews

Dream Away Cottage in Berlin

Come to Dream Away Cottage and experience your Dream Away vacation. Take a drive in the country and shop in our popular shops. Relax in the cottage. Make a cup of coffee, read one of our books, or you might want to play a game. You will enjoy the quiet atmosphere. The shops are only 2 minutes from the cottage. Visit the many attractions close by. Check our guestbook. Read our story. You might be surprised. We have suggestions for you. Talk, laugh, and relax in our TV free zone. We do have Wifi.

Top guest favourite
A modern cabin is featured, surrounded by trees and bathed in golden light from the setting sun. A spacious deck extends from the cabin, providing seating areas, while steps lead down to the gravel path below amidst lush landscaping.
Place to stay in Sugarcreek
4.97 out of 5 average rating, 351 reviews

The Haven / Scenic Aframe cabin

The Haven is just that - a place of rest. Keep it simple at this peaceful and centrally-located place. The cabin is nestled in a wooded area with a pond view and rolling hills. In the heart of beautiful Amish country we are just minutes away from popular attractions. The living area includes a full kitchen, washer and dryer, and comfortable furniture to enjoy a smart tv and fireplace. A King bed and full bath on the main floor. The loft has a queen bed. We welcome you to come stay with us!

Guest favourite
A rustic living area features exposed wooden beams and stone walls, creating a warm ambiance. Comfortable seating surrounds a central coffee table, with soft lighting from table lamps. A cozy fireplace is visible, enhancing the inviting atmosphere of the space.
Cottage in Winesburg
4.96 out of 5 average rating, 104 reviews

Peaceful, Spacious, Historic Stone Cottage Getaway

Located in the quaint village of Winesburg, in the heart of Ohio's Amish Country, the historic Stone Cottage Inn provides all the amenities of home in a rustic ambiance hard to find anywhere else. The peaceful small-town setting offers our visitors easy access to the general store, pizza shop, coffee shop, ice cream parlor, antique store, post office, and the park. Take a stroll on the brick sidewalks, and put your feet up by the fire while you listen to the sound of horses passing by.

Top guest favourite
The rustic cabin features a welcoming exterior with a red metal roof and wooden log walls, surrounded by a lush forest. Soft yellow light emanates from the windows, enhancing the cozy appearance. A softly lit pathway leads to the entrance, inviting guests to explore the peaceful surroundings.
Cabin in Sugarcreek
4.93 out of 5 average rating, 425 reviews

Wildwood Hill Cabin

The acres of woods surrounding Wildwood Hill Cabin offer you peace, quiet, and privacy. The open cathedral design coupled with the strength of the authentic logs invites you to relaxation and a slower pace. Though rustic, the cabin is filled with modern amenities for your comfort and enjoyment. Soak in the hot tub. Snuggle on the couch with hot drinks. Or sit around a fire. This place is crafted for you to relax from your busy schedule. The comfort of the cabin includes WiFi, but no tv.

Top guest favourite
A spacious deck is shown in front of a wooden house, featuring a small round firepit on the grassy lawn. Chairs are positioned on the deck, offering views of the surrounding greenery and hills under a partly cloudy sky.
Home in Dundee
4.98 out of 5 average rating, 110 reviews

Peaceful Meadows/Porch to Sun Yourself/Sandbox

This beautiful home is located in the hills of Amish county, it has plenty of space for the whole family, a gorgeous kitchen with all your basic cooking utensils, a pebble pit and sand box for the kids, and beautiful views of the country side. The home is a short drive from Berlin, a main attraction, with lots of shops, restaurants and places to explore. While tucked back from the main road, there are coffee shops, a pizza place, grocery store, and a dollar general just mins away.

Top guest favourite
A quaint cabin entrance is framed by a covered porch, featuring wooden flooring and surrounded by vibrant potted plants. Two metal chairs provide seating, and a bold red door is prominently displayed, complementing the natural setting of greenery.
Cabin in Winesburg
4.92 out of 5 average rating, 375 reviews

Christi's Hideaway Cabin in Winesburg Ohio

Beautiful cabin sits back below our home. We are located in the beautiful town of Winesburg, Ohio within 5 miles of Mt. Hope , 6 miles from Walnut Creek & 7 miles from Berlin. Ohio. Within walking distance of Whitmer's general store & pizza and the Beacon Cafe. Come & visit our quaint little town and historical buildings. Our address is 2121 Main Street, Winesburg, Ohio 44690. You will have privacy! I have 2 outside cats but they never go inside.

Superhost
A newly installed hot tub is placed on a wooden deck, enclosed by a privacy fence. Steps lead up to the hot tub, which is surrounded by a mix of shadow and sunlight. Light frost can be seen on the surface, indicating a cool temperature.
Cabin in Dundee
4.91 out of 5 average rating, 359 reviews

Black Rock Cabin 1800s Log Cabin In Dundee Ohio

Black Rock Cabin is a historic Log Cabin that has been Completely Renovated. Featuring an open Main floor with living, dining and kitchen space. Upstairs is a full bedroom and bathroom. Experience the tile shower with its gentle rain head, then relax beside a crackling wood fire in the living room. Enjoy the corner kitchen with a stove, oven, fridge, microwave, and coffee maker. Sit at the rustic dining table or pull out bar stools at the counter.

Top guest favourite
Cabin in Strasburg
4.98 out of 5 average rating, 385 reviews

Scandi Cabin•Hot Tub• Fire Pit•

In a quiet neighborhood just out of Strasburg: The White Oak Cabin:•2 bed•2 bath•Hot Tub•Fully stocked kitchen •4 Electric Fireplaces •Living room - 50”TV •Climate control in each room •Step ladder to loft In the loft:•Workspace •1 Huge Sectional-room for 2 to sleep•50” TV •Fireplace 30 minutes > Pro Football Hall of Fame 15 minutes > Sugarcreek (Amish Country)20 minutes > 6 wineries 60min > Cuyahoga Valley National Park

Top guest favourite
A charming entrance is framed by a timber and stone structure, showcasing a welcoming red door. Lush greenery and vibrant hanging plants are positioned above the entrance, complementing the stone finish and adding a natural touch to the exterior.
Guest suite in Wilmot
4.98 out of 5 average rating, 128 reviews

Old Alpine Valley Inn w/Queen Bed in Amish Country

Quiet & cozy 3 room guest suite tucked away at the edge of a lush forest inside the heart of Ohio’s beautiful Amish Country. This welcoming suite has both rustic & modern features. This spot in Amish Country is only a 10-20 minute drive to most of the popular towns in the area. If you’re looking for easy access, peaceful and fresh country air this suite is yours to book.

Popular amenities for Winesburg holiday rentals

  1. Airbnb
  2. United States
  3. Ohio
  4. Holmes County
  5. Winesburg