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, 152 reviews

Pear Tree Cottage ~ A Down Home Christmas 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
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, 260 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
Apartment in Sugarcreek
4.94 out of 5 average rating, 112 reviews

Hidden Glen Retreat

Hidden Glen Retreat is 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 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
4.93 out of 5 average rating, 246 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.

Guest favourite
The tiny house exterior features a modern design with black metal siding and wooden accents. Large windows provide ample natural light, and a welcoming porch is adorned with two white chairs. Lush green grass surrounds the home, creating a serene outdoor space.
Tiny home in Millersburg
4.96 out of 5 average rating, 136 reviews

Farm Lane Guest House

Nestled only one mile from the square in Berlin, this quaint tiny house offers a relaxing retreat for your visit to Amish Country. This charming abode features two cozy bedrooms, a pristine bathroom, a welcoming living area, and a fully-equipped kitchen. Guests can unwind and enjoy a slower pace of life. Whether you’re sipping coffee to start your day or exploring nearby shops and attractions, our tiny house is the perfect place for a memorable retreat.

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, 362 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
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, 109 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, 460 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

Top Guest favourite
A charming entrance is framed by a timber and stone structure, showcasing a welcoming red door. Lush greenery and vibrant hanging plants are positioned above the entrance, complementing the stone finish and adding a natural touch to the exterior.
Guest suite in Wilmot
4.98 out of 5 average rating, 126 reviews

Old Alpine Valley Inn w/Queen Bed in Amish Country

Quiet & cozy 3 room guest suite tucked away at the edge of a lush forest inside the heart of Ohio’s beautiful Amish Country. This welcoming suite has both rustic & modern features. This spot in Amish Country is only a 10-20 minute drive to most of the popular towns in the area. If you’re looking for easy access, peaceful and fresh country air this suite is yours to book.

Guest favourite
A contemporary two-story house is shown, featuring a mix of gray and white siding. A front door with a clean design is flanked by manicured bushes. The surrounding lawn is well-maintained, with a gravel driveway leading to the property.
Tiny home in Holmesville
4.96 out of 5 average rating, 141 reviews

Unique Home in Holmesville/ Holmes County

●20 minutes from Wooster, Millersburg, Berlin, Loudenville, and Mt Hope, and within a short drive to Mohican State Park. ●Firepit and chairs on the back patio ●Built in 2022 with contemporary styling and unique touches throughout. ●Set in the small town of Holmesville with a pizza shop and Blue Moon Bistro close by. ●Quality whole bean coffee provided

Superhost
A treehouse situated among lush green trees, elevated on wooden stilts. The structure features large windows that offer views of the surrounding forest. A staircase leads up to the entrance, surrounded by foliage, creating a secluded retreat in nature.
Treehouse in Dundee
4.87 out of 5 average rating, 212 reviews

Treehouse Village - The Sky Loft

The Sky Loft is a house way up high in the trees! It is what every child's dreams are made of. You will have all you need to enjoy your retreat. There is a queen-sized bed and full bath amenities. This is tiny house living at its best! The deck is located halfway up the stairs, on the first level. The Sky Loft is a unique treehouse offering for sure!

Top Guest favourite
The front view of a single-story home is showcased, featuring a well-maintained lawn and a tree line in the background. A covered porch is visible, along with an inviting front door. The exterior is painted in light tones, complemented by a dark shingle roof.
Home in Sugarcreek
4.98 out of 5 average rating, 131 reviews

High Point Haven

Relax and recharge in our fully furnished peaceful home! Located in Walnut Creek, OH in the heart of Amish Country. This is a great location in a quiet neighborhood centrally located. Two great restaurants just up the street a few minutes away to grab breakfast, lunch or dinner. Berlin is a short 5 minute drive away for more shopping and exploring!

Popular amenities for Winesburg holiday rentals

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