Vacation rentals in Winesburg

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Top-rated vacation rentals in Winesburg

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Top guest favorite
Cottage in Dundee
4.97 out of 5 average rating, 160 reviews

PearTreeCottage~Mini Donkeys•Hot-Tub•Serene Views!

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 favorite
The cabin features a rustic log exterior surrounded by trees with vibrant autumn foliage. A spacious porch, equipped with multiple wooden chairs, invites relaxation. Large windows reflect natural light, enhancing the cabin's warm atmosphere, while the grassy area provides ample space for outdoor enjoyment.
Cabin in Millersburg
4.95 out of 5 average rating, 235 reviews

Mockingbird Hill Lodge

Mockingbird Hill Lodge warmly welcomes you! You may want to retreat for a time with family and friends, surrounded by nature. Or a 5 minute drive will take you to the bustle of our unique small town attractions. Return to the comfort of our 4 bedroom cabin each evening, relax in beds designed for a blissful sleep experience. However you choose , do not miss the joy of greeting the sun over coffee on the front porch swing. You can tuck away the feeling, then relive it as needed to be refreshed!

Top guest favorite
A breakfast spread is presented on a table, featuring French toast topped with strawberries and blueberries, alongside two sausage links. A small bowl of fruit and a cup are visible in the background, complemented by a scenic view outside.
Loft in Dundee
4.96 out of 5 average rating, 309 reviews

Escape to our quiet Loft overlooking Amish Country

Climb the stairs to A modern new fully furnished apartment like house with a nice garage to pull the car in. Enjoy our complimentary Wallhouse freshly ground coffee and treat your taste buds with Coblentz chocolates. Soak in the serene countryside as you relax in our spacious hot tub on your own private deck. Make your stay memorable by ordering in a big country breakfast carefully prepared with farm fresh ingredients by our Amish neighbors in their kitchen and delivered right to your door!

Top guest favorite
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, 336 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 favorite
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, 102 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.

Guest favorite
The rustic cabin features a welcoming exterior with a red metal roof and wooden log walls, surrounded by a lush forest. Soft yellow light emanates from the windows, enhancing the cozy appearance. A softly lit pathway leads to the entrance, inviting guests to explore the peaceful surroundings.
Cabin in Sugarcreek
4.93 out of 5 average rating, 420 reviews

Wildwood Hill Cabin

The acres of woods surrounding Wildwood Hill Cabin offer you peace, quiet, and privacy. The open cathedral design coupled with the strength of the authentic logs invites you to relaxation and a slower pace. Though rustic, the cabin is filled with modern amenities for your comfort and enjoyment. Soak in the hot tub. Snuggle on the couch with hot drinks. Or sit around a fire. This place is crafted for you to relax from your busy schedule. The comfort of the cabin includes WiFi, but no tv.

Top guest favorite
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, 587 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 favorite
Guesthouse in Millersburg
4.99 out of 5 average rating, 280 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, 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 favorite
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.

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, 344 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 favorite
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, 250 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 favorite
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, 475 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