Vacation rentals in Winesburg

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Top-rated vacation rentals in Winesburg

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

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Top guest favourite
Farm stay in Dundee
4.97 out of 5 average rating, 176 reviews

Pear Tree Cottage~Breathtaking Views+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
An outdoor patio area features a wooden deck with a grill surrounded by cozy seating arrangements. Two armchairs and a loveseat, adorned with light cushions, are positioned under a pergola draped with string lights. Potted plants hang from the beams, adding a touch of greenery.
Home in Dundee
4.96 out of 5 average rating, 82 reviews

Charming Farmhouse Near Amish Country

Overview: Farmhouse of Blessing is a lovely cottage set in Holmes County, OH, home to one of the nations largest Amish populations. You will enjoy our sparkling clean home that offers a calm and relaxing environment. We also offer free late Sunday checkout. No checking out until 4:00. We have a fully equipped kitchen, spacious living area with original brick and beams, and a lovely outdoor patio area. There are two bedrooms, a pull out couch in the dining room, and two full bathrooms. The laun

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, 364 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, 478 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, 107 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
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
4.97 out of 5 average rating, 119 reviews

Peaceful Meadows/Outdoordining/Breo Firepit/Grill

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
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, 174 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
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, 640 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 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, 387 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.

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, 274 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, 404 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 modern kitchen features a large wooden island with seating for six. White cabinets and open shelves provide ample storage, while a stainless steel refrigerator and stove are prominently displayed. Pendant lights hang above the island, illuminating the space.
Apartment in Dundee
4.99 out of 5 average rating, 502 reviews

Hidden Meadow's Apartment in a Quiet Setting

This quaint apartment 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

Popular amenities for Winesburg vacation rentals