Holiday rentals 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
An outdoor patio area features a wooden deck with a grill surrounded by cozy seating arrangements. Two armchairs and a loveseat, adorned with light cushions, are positioned under a pergola draped with string lights. Potted plants hang from the beams, adding a touch of greenery.
Home in Dundee
4.96 out of 5 average rating, 81 reviews

Charming Farmhouse Near Amish Country

Overview: Farmhouse of Blessing is a lovely cottage set in Holmes County, OH, home to one of the nations largest Amish populations. You will enjoy our sparkling clean home that offers a calm and relaxing environment. We also offer free late Sunday checkout. No checking out until 4:00. We have a fully equipped kitchen, spacious living area with original brick and beams, and a lovely outdoor patio area. There are two bedrooms, a pull out couch in the dining room, and two full bathrooms. The laun

Top guest favourite
Cottage in Dundee
4.97 out of 5 average rating, 167 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
Home in Dundee
5 out of 5 average rating, 18 reviews

Pondside Abode

Welcome to your home away from home! This cozy and stylish 2-bedroom home is prefect for couples, friends, family, or business travelers. 💫What you'll love: • 2 cozy bedrooms with queen beds •fully equipped Spacious kitchen •Comfortable living room with tv •Fast wi-fi •Dedicated coffee bar for your morning brew • Spacious bathroom • Easy self check-in & hassle free stay • Outdoor patio with campfire •located in winesburg. 11 minutes from Berlin ohio 8 minutes from walnut creek ohio

Top guest favourite
A rustic cabin is nestled among lush greenery, surrounded by trees. A gravel pathway leads to the entrance, while a wooden deck with steps is visible. The natural setting offers a sense of privacy and tranquility.
Cabin in Beach City
4.98 out of 5 average rating, 960 reviews

Woodland at Creekside Dwellings w/Hot Tub

The Woodland at Creekside Dwellings is a refreshing getaway for 2, nestled in the forest, near beautiful Amish Country! Only 6 miles from Winesburg and 12.6 Miles from Berlin, you can choose to go out and explore (Dundee Falls is a must see for the explorers! An easy 5 min drive away!) , or cozy up and enjoy nature here! The Pro Football Hall of Fame is only 30 minutes away, as well! There are an endless supply of local attractions. The cabin is stocked and ready for you to unwind and relax.

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, 355 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, 104 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
Cottage in Dundee
4.97 out of 5 average rating, 39 reviews

Whimsical Cottage w/ Pond View

🌿Take in the beauty and serenity of Amish Country at this idyllic cottage in Winesburg! This 1-bed & 1-bath cozy cottage is surrounded by tall trees and overlooking an on-site pond that you can fish on! Our lovely little house has a dressing room, kitchenette, upstairs bedroom and seating area with a tv. Complete with a screened-in porch that’s perfect for enjoying the soothing sounds of nature with your morning coffee, this is the dreamiest spot for you to rest and recharge.

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, 378 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, 360 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
Cabin in Strasburg
4.98 out of 5 average rating, 388 reviews

Scandi Cabin•Hot Tub• Fire Pit•

In a quiet neighborhood just out of Strasburg: The White Oak Cabin:•2 bed•2 bath•Hot Tub•Fully stocked kitchen •4 Electric Fireplaces •Living room - 50”TV •Climate control in each room •Step ladder to loft In the loft:•Workspace •1 Huge Sectional-room for 2 to sleep•50” TV •Fireplace 30 minutes > Pro Football Hall of Fame 15 minutes > Sugarcreek (Amish Country)20 minutes > 6 wineries 60min > Cuyahoga Valley National Park

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, 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

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, 129 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.

Popular amenities for Winesburg holiday rentals

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