Holiday houses in Winesburg

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Top-rated holiday rentals in Winesburg

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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, 505 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
The exterior of a charming guesthouse is depicted, featuring white siding and a welcoming front door. Colorful flower beds with seasonal blooms frame the entrance, while a small decorative archway adds visual interest. A well-maintained lawn surrounds the building, enhancing the inviting atmosphere.
Guesthouse in Millersburg
4.99 out of 5 average rating, 189 reviews

Old Veterinarian Office, Heart of Amish Country!

In 1946 my parents lived here, using the upstairs as dad's veterinarians office. I've remodeled it using their doors, sinks, and artwork, an Amish made bed & bedding, and included locally made soaps & coffee. My parents were simple, peaceful, and relaxed, and I hope you feel that during your stay. This unique building has one bedroom, one bathroom, a small living area with a pull-out couch and kitchen. It is located just minutes away from downtown Berlin, local farms, bakeries and so much more!

Guest favourite
A cozy sleeping area features a spacious bed with a textured blanket and decorative headboard. Two accent chairs sit beside a small side table, complemented by warm lighting from bedside lamps. Soft rugs cover the floor, adding to the welcoming atmosphere.
Apartment in Wooster
4.84 out of 5 average rating, 296 reviews

Cozy Abode

The space is a dedicated basement apartment. The space has its own door and lock, but guests will enter through a shared garage entrance. The decor is neat and modern. There is a small kitchenette, giving guests the ability to eat in, or make coffee. The cozy sitting area is a great place to wind down for the evening or enjoy a morning cup of coffee. The apartment is below our living space. While we will do our best to keep noise to a minimum, you will hear kids/footsteps during the day.

Guest favourite
Apartment in Sugarcreek
4.93 out of 5 average rating, 102 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, 242 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
A living room is presented with a green accent wall and features two comfortable black leather sofas facing a wooden coffee table. An antique cabinet and a wall-mounted deer head add character, while softly lit recessed lighting enhances the cozy setting.
Apartment in Dundee
4.96 out of 5 average rating, 115 reviews

Peaceful Hills

Looking for a quiet place to come relax in Amish Country? This is the place for you to stay. We are back in the hills of Amish Country where it’s quiet and relaxing. We are 4 miles from Sugarcreek, 5 miles from Walnut Creek and 9 miles from Berlin. Come bring the whole family to this great place with lots of room, 2 Bedrooms with Queen beds, 2 Bathrooms, plus a cot and single mattress available, full kitchen and living room, 1900 SQ FT NO PETS, NO SMOKING, NO DRINKING

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, 162 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
4.91 out of 5 average rating, 352 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, 315 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
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, 102 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, 448 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
The exterior features a spacious wooden deck supported by a structured wooden frame. A barbecue grill is positioned next to an outdoor dining area, complemented by modern seating. Large glass doors provide a view into the interior space, enhancing the seamless indoor-outdoor connection.
Home in Sugarcreek
4.96 out of 5 average rating, 112 reviews

Hollow Valley Crates

Nestled in a flowy little valley, Hollow Valley Crate's "Hilltop" Container is your new favorite place to rest, relax and recover. We're a few minutes from interstate 77 and a few minutes from the heart of Amish Country. Surrounded by wineries and local dining favorites you won't want to miss. Spooky Hollow Road is quiet and peaceful. What more can you ask for when needing a get away?

Popular amenities for Winesburg holiday rentals

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