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
An open-concept living space features a well-equipped kitchen with a central island and seating for four. A dining area with white chairs and a round table is visible, alongside a cozy sitting area highlighted by a rug. Decorative lighting fixtures enhance the inviting atmosphere.
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, 165 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
Guest house in Millersburg
4.99 out of 5 average rating, 291 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 cabin is framed by trees, situated beside a serene pond. A sloped lawn leads to the water, where outdoor seating and lounge chairs are visible on the deck. The soft glow of sunlight reflects on the pond's calm surface.
Place to stay in Sugarcreek
4.97 out of 5 average rating, 348 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!

Top guest favourite
The exterior of the bungalow is shown, featuring a two-story design with a gabled roof and white siding. A porch with wooden rockers is adorned with hanging plants. Lush green landscaping complements the structure, set against a misty sky.
Home in Millersburg
4.97 out of 5 average rating, 120 reviews

Bunker Hill Bungalow

The Bungalow is located in the heart of Amish Country in the tiny town of Bunker Hill, only 4 minutes from Berlin. Sample amazing cheese at Heini's Cheese or grab delicious donuts at Kauffman's Country Bakery. After that, visit the shops at Ohio's Market. All within walking distance. In the evening, relax on the porch and watch the Holmes Co. traffic clip clop by while playing games with the family. This is an 'Off-the-Grid' home (with great cell service) completely powered by solar panels.

Top guest favourite
Place to stay in Beach City
4.98 out of 5 average rating, 455 reviews

Forest lane Aframe, Soak Tub, Kayaks, Campfire

Forest Lane Aframe - @forestlane__ 1 hr from Cuyahoga National Park Escape to a cozy, A-frame cabin nestled among trees, overlooking a serene pond with a fountain. Enjoy mornings with fresh local coffee on the deck, afternoons kayaking , evenings soaking in the deep tub or unwinding by the indoor fireplace or outdoor campfire area . This relaxing space offers everything you need to unplug and recharge - nature, comfort, and a touch of romance - The perfect couples or solo getaway

Superhost
The charming exterior of the brick cottage features a white facade with a sloped roof. Two large windows adorn the front, framed by hanging planters. A wooden door serves as the entrance, flanked by a landscaped yard with fresh greenery and a stone walkway leading to the door.
Cottage in Wilmot
4.85 out of 5 average rating, 123 reviews

Maple Street Manor

Welcome to Maple Street Manor... We invite you to be our guests at this 1892 dreamy Brick Cottage full of rich history + charm in Amish Country, Ohio. Take a step back in time as you visit this peacefully rural area, bursting with unique experiences and great food! Maple Street Manor is located in the small, sleepy town of Wilmot - just a short drive from all of the hotspots! If you love character and appreciate original (squeaky) hardwood floors... this is just the space for you!

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 scenic view of rolling hills and open fields is captured from the property, showcasing a serene landscape under a gentle overcast sky. Neat rows of evergreen shrubs border a reflecting pond, enhancing the tranquil outdoor space.
Cottage in Dundee
4.94 out of 5 average rating, 276 reviews

Private Romantic stone cottage in Amish country

Romantic cottage in the rolling hills of Amish Country. Treat your taste buds to a mouthwatering full breakfast delivered to your door! Come and loose all your cares as you breathe in the quiet serene countryside. Wonderfully decorated complete with a full kitchen and a two person jaccuzzi overlooking the breathtaking view. Feast your eyes on spectacular sunsets in front of a warm fire in our handcrafted fire pit as the sound of running water from the pond fills the air.

Top guest favourite
The A-frame cabin is nestled among trees, featuring large windows that provide a view of the surrounding wooded area. A wooden walkway leads to the entrance, connecting the cabin to the natural landscape. The exterior showcases a blend of natural materials with a modern design.
Cabin in Beach City
4.98 out of 5 average rating, 611 reviews

A-frame at Creekside Dwellings w/Hot Tub

The A-frame at Creekside Dwellings is a small + impactful oasis near beautiful Amish Country! Only 6 miles from Winesburg + 13 miles from Berlin. There are an endless supply of local attractions. The Pro Football Hall of Fame only 30 minutes away, as well! The A-frame is stocked with all the amenities you will need to kick back and relax! Enjoy the steaming hot tub, gas grill, and tree top views. *note on location: the A-frame is visible from the road during the winter months

Top guest favourite
A tiny home is nestled among trees, featuring a small front porch with steps leading up. A covered gazebo stands nearby, surrounded by a gravel patio area. The property is framed by vibrant autumn foliage, providing a serene backdrop.
Tiny home in Beach City
4.95 out of 5 average rating, 169 reviews

Klein haus ~ Tiny Home

Reconnect with nature at Klein Haus! You'll love this unique and romantic escape. A true Tiny Home experience. Including a patio area with comfortable seating, hot tub, cold plunge. Out the windows you'll see views of the wooded area that surround the property, along with hopefully some glimpses of wildlife! Klein Haus has its own parking area. We are within 20 minutes of Berlin, the Heart of Amish Country. So come ready to be refreshed, & to have a relaxed getaway!

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.

Popular amenities for Winesburg holiday rentals

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