Holiday houses in Winesburg

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Top-rated holiday rentals in Winesburg

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

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Top Guest favourite
A dining area features a round wooden table surrounded by four matching chairs, with a decorative plant as the centerpiece. Nearby, a leather chair sits beside a window, while a kitchen area displays white cabinetry and dark appliances, providing a functional and inviting space.
Home in Sugarcreek
4.97 out of 5 average rating, 541 reviews

Gerber Valley Farm Bed & Breakfast

Spend the night "on the farm" in a scenic valley between the rolling hills of Holmes County, Ohio--the heart of Amish Country. Walnut Creek, Berlin, and Sugarcreek are mere minutes away! We offer a private setting so you can relax and breathe in the country air! Sit on the porch and watch the buggies roll by while you enjoy Chris' famous coffeecake--a favorite of our many returning guests! Soak in the whirlpool tub and let your cares float away. You will love our clean, cozy, and charming place!

Top Guest favourite
Cottage in Dundee
4.97 out of 5 average rating, 169 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
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, 236 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 favourite
The exterior of the bungalow is shown, featuring a two-story design with a gabled roof and white siding. A porch with wooden rockers is adorned with hanging plants. Lush green landscaping complements the structure, set against a misty sky.
Home in Millersburg
4.97 out of 5 average rating, 126 reviews

Bunker Hill Bungalow

The Bungalow is located in the heart of Amish Country in the town of Bunker Hill, only 4 minutes from Berlin. Sample amazing cheese at Heini's Cheese or grab delicious donuts at Kauffman's Country Bakery (open Sundays). Also visit the shops at Ohio's Market. All within walking distance. In the evening, relax on the porch and watch the Holmes Co. traffic clip clop by while playing games with the family. This is an 'Off-the-Grid' home (with great cell service) completely powered by solar panels.

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, 359 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
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, 105 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 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, 183 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, 379 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 Sparrow's Nest Cottage is showcased, featuring a modern design with a distinctive white façade and a metal roof. The front porch is adorned with rocking chairs, inviting relaxation, while large windows create a bright and open appearance. Green fields surround the cottage.
Cottage in Millersburg
4.99 out of 5 average rating, 264 reviews

Sparrows Nest by Olde Orchard Cottages

Welcome to Sparrow's Nest 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 Sparrow's Nest + Apple Blossom - nestled within the serene rolling hills in the heart of beautiful Amish Country.

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, 364 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
Tiny home in Dalton
5 out of 5 average rating, 263 reviews

Tiny House on Jericho with Hot Tub

Reconnect at this unforgettable escape. Everything you need for a couple's getaway, in a small space! Our tiny house is packed with the necessary amenities and beyond. Relax in the hot tub, enjoy the fire pit (firewood & starter provided), or take a one minute trip to Kidron, where you will find the world-famous Lehman's store. We are also less than 30 minutes from Berlin, Ohio and all the shops and restaurants it has to offer.

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, 494 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