Holiday rentals 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, 159 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 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, 328 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 private back porch is illuminated by string lights, featuring a hot tub and a fire pit on a wooden deck. Surrounded by potted plants, the area provides a relaxing outdoor space for gatherings under the night sky.
Home in Beach City
4.95 out of 5 average rating, 177 reviews

Peaceful, Quiet Country Guesthouse with Hot Tub

Welcome to your peaceful country oasis , just a 15 minute drive to local tourist attractions , as well as 1/2 mile from Dundee Falls. This four bedroom, two bathroom home that comfortably sleeps 8-10 is a perfect choice for a memorable getaway. Nestled along a row of pine trees, this unique modern farmhouse with wood accents makes this home stand out among the rest. After a fun filled day of shopping you’ll love taking a soak in the hot tub under the stars on your private back porch

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, 260 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
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, 580 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 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, 172 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
The cabin features a distinctive A-frame design with a stone chimney and large windows. Surrounded by lush greenery, the exterior includes a covered porch and a cozy pavilion on the side, creating a serene outdoor setting.
Cabin in Millersburg
4.98 out of 5 average rating, 118 reviews

Oasis Retreat in Amish Country

Welcome to the Oasis Retreat Cabin! this cabin was finished in 2017 and has 3 bedrooms, 2 full baths, sleeps 6 comfortably with amazing amenities for you to enjoy! Tucked in the heart of Amish Country, you are surrounded by the beauty of nature! The perfect place to relax and unwind! 1 mi from shopping and food in the famous Berlin shopping area! * Note: If you see another listing that looks just like this one, it is the same property, just a new host.

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.

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, 341 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
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, 244 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 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.
Flat in Dundee
4.99 out of 5 average rating, 470 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

Superhost
A charming treehouse is elevated above the forest floor, featuring dark wooden siding and large windows. A spacious deck surrounds the house, providing a welcoming entrance. A wooden swinging bridge connects the treehouse to the ground, adorned with soft glowing lights along the pathway.
Treehouse in Dundee
4.83 out of 5 average rating, 192 reviews

Treehouse Village - The Shack

The Shack is what dreams are made of! Enter over a 40 foot swinging bridge, then step into a house in the woods! There is a full bath, a kitchenette, and a day bed/ lounge area on the main floor. A European style ladder takes you up into the loft where you'll find your queen-sized bed sleeping area. Outside you can warm by the fire on a deck large enough for the family.

Popular amenities for Winesburg holiday rentals

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