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
Cottage in Dundee
4.97 out of 5 average rating, 168 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
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, 356 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 A-frame cabin is nestled among trees by a tranquil pond. Its unique triangular design features large windows and a welcoming front porch. A fountain creates gentle ripples on the water's surface, enhancing the serene environment.
Place to stay in Beach City
4.98 out of 5 average rating, 463 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

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, 105 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
An aerial view of a log cabin is presented beside a tranquil pond, surrounded by lush greenery and gentle hills. The driveway leads up to the cabin, offering a clear view of its rustic design and the serene water reflecting the surrounding landscape.
Cabin in Millersburg
4.98 out of 5 average rating, 164 reviews

Stillwater Cabin with Hot Tub

A beautiful log cabin located in Berlin Ohio, the heart of Amish Country. Nestled beside an 8-acre pond with an open dock and adirondack chairs. The outdoors offers other relaxing options like soaking in the hot tub, putting on the putting green, sitting under the pergola with the gas fire pit, swinging on the front porch, or grilling on the patio. Or you can head indoors and relax on the massage chair, play a game, or watch something on one of the 4 TV's, or simply take a nap.

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, 282 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, 623 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 bright living area features two dark sofas arranged around a central coffee table. Natural light filters through multiple windows, complemented by a sleek television mounted above a decorative fireplace. A balanced mix of greenery and artwork adds visual interest to the neutral-toned walls.
Home in Dundee
4.99 out of 5 average rating, 183 reviews

Evergreen Place at Winesburg

Evergreen Place at Winesburg is your private get-away in the heart of Amish Country. Relax to the sound of buggies passing by, watch the sunset or baseball games from the comfort of the wrap around deck. The gardens include a swing set, a pergola covered seating and dining area complete with lights and shades. Even enjoy freshly picked herbs, fruits and vegetables when in season. Stroll down the street to eating, shopping, parks and the beauty that is Winesburg!

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, 379 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, 362 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
The exterior of Apple Blossom Cottage is showcased with a modern white facade and a distinctive metal roof. A welcoming porch features rocking chairs and a scenic view of the rolling hills in the background. The landscape includes well-maintained greenery and a gravel pathway.
Cottage in Millersburg
4.99 out of 5 average rating, 262 reviews

Apple Blossom by Olde Orchard Cottages

Welcome to Apple Blossom Cottage... We invite you to be our guest! For years Mary + John, the founders of White Cottage Company, dreamed of creating a space for people to retreat to that would be so cozy, peaceful, and relaxing that guests wouldn't want to leave! Their dream is now a reality with the completion of Olde Orchard Cottages Apple Blossom + Sparrow's Nest - nestled within the serene rolling hills in the heart of beautiful Amish Country.

Top guest favourite
Cabin in Strasburg
4.98 out of 5 average rating, 390 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

Popular amenities for Winesburg holiday rentals

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