Winesburg holiday homes

We found 277 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Winesburg to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include air conditioning and a pool. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Winesburg

Showing deals for:18 Dec - 25 Dec

Exterior
Dining
Living area
Living area
Exceptional
(20 reviews)

Peaceful Pastures

Fredericksburg

22% off
NZ$1,676
for 7 nights, 1 room
NZ$239 per night
includes taxes & fees
Peaceful Pastures
Outdoor dining
Exterior detail
Private kitchen
Dining
Exceptional
(134 reviews)

Kate's Guest House "Hidden Retreat"

Millersburg

8% off
NZ$5,230
for 7 nights, 1 home
NZ$747 per night
includes taxes & fees
Kate's Guest House "Hidden Retreat"
Loft bedroom
Exterior
The built in dinette directly beside the full kitchen
The main entrance into the walkout basement
Exceptional
(255 reviews)

Wrap Around Decks w/Beautiful View & Hot Tub

Dundee

8% off
NZ$2,110
for 7 nights, 1 cottage
NZ$301 per night
includes taxes & fees
Wrap Around Decks w/Beautiful View & Hot Tub
Interior
Private deck space with grill and extra seating
Front porch and entryway
View from the loft area
Exceptional
(86 reviews)

Cabin in Amish Country w Animals - 1 mile from Berlin, Ohio

Millersburg

13% off
NZ$2,614
for 7 nights, 1 cabin
NZ$373 per night
includes taxes & fees
Cabin in Amish Country w Animals - 1 mile from Berlin, Ohio
Front steps.
Kitchen
Hot tub.
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Exceptional
(141 reviews)

Riverside Retreat with Hot Tub

Strasburg

9% off
NZ$2,606
for 7 nights, 1 home
NZ$372 per night
includes taxes & fees
Riverside Retreat with Hot Tub
Room
Dining
Living area
Terrace/patio
Exceptional
(295 reviews)

Kingsway Guesthouse. Come, relax, and enjoy your time in Amish country!

Millersburg

9% off
NZ$2,809
for 7 nights, 1 home
NZ$401 per night
includes taxes & fees
Kingsway Guesthouse. Come, relax, and enjoy your time in Amish country!
Sunroom / Entrance
Home access is through the front door facing the road.
Backyard / Enclosed Patio / Deck
Dining Room
Exceptional
(9 reviews)

The Berlin Guesthouse

Berlin

8% off
NZ$4,919
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
The Berlin Guesthouse
Beverage Station
living room with power recliner, queen size sleeper sofa, smart TV and 2 chairs
Large, fully stocked kitchen
Kitchen with bar and 4 stools
Exceptional
(71 reviews)

The Kidron Quilter's Home, relax in Amish country with the locals

Dalton

9% off
NZ$2,185
for 7 nights, 1 home
NZ$312 per night
includes taxes & fees
The Kidron Quilter's Home, relax in Amish country with the locals
microwave, kitchen , indoor, coffee & coffee maker, oven, refrigerator, stovetop, dishwasher
Exterior detail
Living area
summer, terrace patio, outdoor, dining table, unit views, daytime, property exterior
Exceptional
(23 reviews)

Cozy 2-bedroom home in Winesburg, holmes county ohio

Dundee

9% off
NZ$2,152
for 7 nights, 1 home
NZ$307 per night
includes taxes & fees
Cozy 2-bedroom home in Winesburg, holmes county ohio
Exterior detail
Private kitchen
Interior
Room
Exceptional
(9 reviews)

Romantic, Luxurious Getaway in the Heart of Amish Country

Sugarcreek

8% off
NZ$2,405
for 7 nights, 1 home
NZ$344 per night
includes taxes & fees
Romantic, Luxurious Getaway in the Heart of Amish Country
Dining
Living area
Interior
Private kitchen
Exceptional
(13 reviews)

Crystal Wave Retreat, Berlin Ohio Hot tub and pool

Berlin

8% off
NZ$7,315
for 7 nights, 1 home
NZ$1,045 per night
includes taxes & fees
Crystal Wave Retreat, Berlin Ohio Hot tub and pool
Interior
Private kitchen
Exterior detail
Exterior
Exceptional
(58 reviews)

Family Friendly Barndominium in Amish Country (Sleeps 8)

Millersburg

9% off
NZ$3,504
for 7 nights, 1 cabin
NZ$501 per night
includes taxes & fees
Family Friendly Barndominium in Amish Country (Sleeps 8)
Interior
You’ll love this backyard! Private & peaceful.
Interior
Peaceful Retreat away from it all
Exceptional
(23 reviews)

Great 3 Bedroom Log House in Amish Country

Dover

9% off
NZ$3,319
for 7 nights, 1 home
NZ$474 per night
includes taxes & fees
Great 3 Bedroom Log House in Amish Country

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Winesburg getaway

Learn about the unique charm of Winesburg with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winesburg

Are you searching for attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Winesburg a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • The Farm at Walnut Creek (6.9 mi / 11.1 km)
  • Breitenbach Wine Cellars (9.8 mi / 15.7 km)
  • Coblentz Chocolate Company (5.4 mi / 8.7 km)
  • Baylor Beach Park (7.1 mi / 11.4 km)
  • Swiss Heritage Winery (9.7 mi / 15.7 km)
  • Black Diamond Golf Course (13.3 mi / 21.4 km)

Exploring the natural landscape of Winesburg

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Winesburg is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • The Wilderness Center (4.8 mi / 7.8 km)
  • Community Park (5.6 mi / 9 km)
  • Sunset Lake (7.9 mi / 12.7 km)
  • Meadow Lake (8.1 mi / 13.1 km)
  • Spring Valley Lake (9.2 mi / 14.7 km)
  • Kidron Evergreen Park (9.2 mi / 14.8 km)

Transport to and around Winesburg

Fly into Akron, OH (CAK-Akron-Canton), the closest airport, located 24.7 mi (39.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Winesburg when booking a holiday rental?
When considering a holiday rental in Winesburg, Ohio, the most appealing area is the heart of the town, which offers a charming blend of tranquillity and local charm. This area features a selection of properties that reflect the quaint character of the village, superb for those seeking a peaceful retreat. You can find a variety of accommodations, from cosy cottages to family-friendly homes, providing a delightful base for your stay.One of the top attractions nearby is the Winesburg Historical Society, where visitors can experience firsthand the rich local history and learn about the heritage of the region. Additionally, the scenic surroundings offer beautiful landscapes and opportunities for outdoor activities, making it a great spot for nature enthusiasts. The local community often hosts events that showcase the area's culture, providing visitors with a genuine experience of small-town life in Ohio.
What is the most popular type of holiday rental accomodation in Winesburg?
In Winesburg, holiday houses and cottages are the most popular types of holiday rental accommodations, with several options available throughout the area. These rentals typically offer a homely atmosphere, featuring amenities like fully equipped kitchens, comfortable living spaces, and outdoor areas for relaxation. Many properties are set in peaceful surroundings, making them ideal for families or groups seeking a serene getaway.
Are there any family house rentals in Winesburg?
In Winesburg, Ohio, there are several family-friendly house rentals available, making it a charming option for visitors. This quaint town offers a peaceful atmosphere, ideal for families looking to unwind. Many of the properties feature spacious living areas, fully equipped kitchens, and outdoor spaces where children can play safely.Visitors can also enjoy the nearby attractions, such as local parks and nature trails, which provide opportunities for outdoor activities and exploration. The welcoming community and the picturesque surroundings make Winesburg a delightful destination for family gatherings.
Are there pet-friendly house rentals in Winesburg?
In Winesburg, there are several pet-friendly house rentals available for travellers looking to enjoy a comfortable stay with their furry companions. The area features charming homes that often come with amenities such as spacious backyards, fully equipped kitchens, and cosy living areas, ensuring a pleasant experience for both pets and their owners.
Are there any remote work holiday rentals in Winesburg?
In Winesburg, Ohio, there are several remote work holiday rentals available, with around 12 options for those looking to balance work and leisure. These accommodations typically offer essential amenities such as Wi-Fi in rooms, ensuring that guests can stay connected during their stay. Many properties also provide access to third-party internet services, which can be beneficial for remote workers requiring reliable connectivity.The area is characterised by its quaint rural charm, making it a peaceful setting for work. Guests can expect comfortable living spaces that may include designated work areas, allowing for a productive environment while enjoying the beautiful surroundings. Additionally, properties often permit events, making them suitable for small gatherings or meetings. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Winesburg?
In Winesburg, popular rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios that provide outdoor spaces for relaxation and enjoying the fresh air. Many properties also feature coffee and tea makers, ensuring that guests can start their day with a warm beverage. Dining areas are common, creating a comfortable setting for shared meals. Additionally, fireplaces are often included in these rentals, adding a cozy touch for those cooler evenings.
When is the best time to visit Winesburg for a holiday rental?
October is the most popular time to visit Winesburg, Ohio, when the landscape transforms into a stunning tapestry of autumn colours. This month attracts visitors who appreciate the beauty of fall foliage and enjoy the charming, small-town atmosphere that Winesburg offers. With temperatures typically ranging from 4 to 15 degrees Celsius, the crisp air creates a comfortable environment for outdoor activities like hiking and leisurely strolls through the local parks.The peak season in Winesburg spans from June to August, when families and tourists flock to the area for summer activities and events. This vibrant period often features local festivals and farmers' markets, making it an excellent time for those seeking a lively experience. However, if you prefer a quieter visit, October presents a superb opportunity to explore the region at a more relaxed pace, while still enjoying an array of seasonal events and local attractions.For those who are budget-conscious, consider visiting in November, which typically sees a decrease in tourist numbers. While the fall foliage will have faded, this month can still offer a peaceful retreat, allowing for a genuine connection with the community and a chance to experience local traditions without the crowds.In summary, whether you seek the vibrant energy of summer or the serene beauty of autumn, Winesburg has something special to offer in any season.
What are the top attractions in Winesburg?
In Winesburg, Ohio, visitors can engage in the charm of this small town, which is often associated with the works of author Sherwood Anderson. The heart of the town features quaint shops and local eateries that reflect the region's heritage. The Winesburg Historical Society offers insights into the town's past and is a great starting point for exploring local history. Nearby, the picturesque countryside provides opportunities for leisurely walks and enjoying the natural beauty of rural Ohio.
Are all fees included in the Winesburg holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winesburg holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Winesburg with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winesburg holiday homes?
You can find great discounts on holiday homes in Winesburg on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winesburg holiday home booking on Bookabach?
To find Winesburg holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Winesburg?
A long-stay holiday home in Winesburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winesburg holiday home?
Book your Winesburg holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winesburg?
Prices for holiday homes in Winesburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Winesburg to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.