Holiday houses in Winesburg

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Top-rated holiday rentals in Winesburg

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Top Guest favourite
Cottage in Dundee
4.97 out of 5 average rating, 155 reviews

Pear Tree Cottage ~ A Down Home Winter Getaway

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 exterior of a charming guesthouse is depicted, featuring white siding and a welcoming front door. Colorful flower beds with seasonal blooms frame the entrance, while a small decorative archway adds visual interest. A well-maintained lawn surrounds the building, enhancing the inviting atmosphere.
Guesthouse in Millersburg
5 out of 5 average rating, 205 reviews

Old Veterinarian Office, Heart of Amish Country!

In 1946 my parents lived here, using the upstairs as dad's veterinarians office. I've remodeled it using their doors, sinks, and artwork, an Amish made bed & bedding, and included locally made soaps & coffee. My parents were simple, peaceful, and relaxed, and I hope you feel that during your stay. This unique building has one bedroom, one bathroom, a small living area with a pull-out couch and kitchen. It is located just minutes away from downtown Berlin, local farms, bakeries and so much more!

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
4.96 out of 5 average rating, 320 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
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, 110 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
A modern kitchen is equipped with stainless steel appliances, including a refrigerator and a stove. A wooden dining table with black chairs is positioned near a window that allows natural light to illuminate the space. Neutral-toned decor and simple shelving enhance the room's functionality.
Guesthouse in Millersburg
4.99 out of 5 average rating, 266 reviews

Dream Away Cottage in Berlin

Summer is here. 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, sit in the hickory rocker and 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.

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, 250 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
Apartment in Sugarcreek
4.92 out of 5 average rating, 118 reviews

Hidden Glen Retreat

Hidden Glen Retreat - a cozy apartment nestled beside the woods, where the lights are left on for you if you come in late and you wake up to the music of birdsong! Enjoy your morning coffee on the deck or gather around the gas fireplace with your family or a friend. Located in the village of Walnut Creek, Ohio minutes from Der Dutchman Restaurant, Rebecca's Bistro, Hillcrest Orchard, and Cafe Chrysalis, and a short drive (10 - 15 minutes) from Sugar Creek, Berlin, and Mt Hope.

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
4.94 out of 5 average rating, 155 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, 366 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
Cabin in Dundee
4.99 out of 5 average rating, 109 reviews

Andrew’s Cabin next to the Dundee falls

Take a break and relax at this breath taking newly built in 2023 unique and tranquil getaway. 15 mins from Berlin . An . Everything you need to enjoy your vacation to Amish Country. Located only 15 minutes to downtown Berlin and Walnut Creek, Short hike to the Dundee Falls, 15 minutes to Dover, 30 minutes to Canton. Both bedrooms have a Tempur-Pedic mattress! TV in the living room has every channel you can think of! Free Wi-Fi.

Top Guest favourite
A modern tiny home features an angled roof and large glass windows, allowing natural light to fill the interior. A spacious deck extends around the structure, complemented by a grassy area in the foreground, contributing to the serene surroundings.
Tiny home in Sugarcreek
4.99 out of 5 average rating, 116 reviews

The Alder

Our serene tiny home offers clean lines and airy spaces that invite you to unwind and rest. Experience a stay where simplicity and comfort blend together seamlessly, providing you with a delightful escape from the hustle and bustle of everyday life Whether you want to sit by the fire or go on an adventure, The Alder is your ideal destination. Located in the heart of Amish Country with many local attractions.

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, 465 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 holiday rentals

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