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
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
Guesthouse 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 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, 349 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, 456 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, 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
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, 107 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
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, 613 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 homes 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 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, 180 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, 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
4.9 out of 5 average rating, 356 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
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, 488 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

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