Winesburg vacation rentals

We found 269 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Winesburg to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for spending time at your vacation home, which might include WiFi and a washer and dryer, You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Winesburg

Showing deals for:May 22 - May 29

Image gallery for Peaceful Pastures

Living area
9.6 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Peaceful Pastures

Fredericksburg

23% off
Price is $137
$960 for 7 nights
All fees included
Peaceful Pastures

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Find out more about Winesburg

Why visit Winesburg

  • Outdoor Adventures: Enjoy scenic township roads and explore the natural beauty of nearby Holmes County.
  • Cultural Experiences: Discover local museums and historic houses that reflect the rich history of Winesburg.
  • Family-Friendly Attractions: Engage in activities suitable for all ages, making it perfect for family vacations.
  • Charming Accommodations: Choose from a variety of cozy cabins, private homes, and delightful cottages for a comfortable stay.
  • Welcoming Community: Experience the warm atmosphere and friendly locals, enhancing your getaway experience.

Popular types of accommodation in Winesburg

Planning a getaway to Winesburg? You're in for a treat. Explore our top vacation rental options, including charming private homes, cozy cabins, and delightful cottages. Enjoy the convenience of equipped kitchens and laundry facilities, like the inviting grapevine house or the quaint cottage inn. With transparency and savings at the forefront, you can relax knowing you'll find the perfect spot to unwind in this picturesque destination.

  • Houses: The top choice for visitors in Winesburg, offering spacious and comfortable living options for families or groups.
  • Cabins: A close second, these charming accommodations provide a rustic retreat amidst nature.
  • Cottages: Cozy and quaint, cottages are ideal for a peaceful getaway in this picturesque area.
  • Apartments: Convenient and often centrally located, apartments are a practical option for travelers seeking flexibility.
  • Bed And Breakfast: A delightful experience, these establishments offer a warm atmosphere and homemade breakfasts.**

Top attractions near Winesburg

Winesburg, Ohio, offers a delightful mix of outdoor adventures and cultural experiences, making it an ideal vacation spot. Visitors can explore historic houses, delve into archaeology and anthropology, and enjoy local museums. This charming town is perfect for families and travelers seeking a blend of scenic beauty and enriching activities, ensuring a memorable getaway for everyone.

  • Yoder's Amish Home: Experience the charm of Amish culture through guided tours of this historic home. Enjoy traditional crafts, homemade treats, and the serene countryside, providing a glimpse into a simpler way of life, just 3 miles from Winesburg.
  • Mt. Hope Event Center: A hub for conferences and events, this venue fosters a professional atmosphere. Located 5 miles away, it hosts various gatherings, making it an ideal place for networking and community engagement.
  • Amish and Mennonite Heritage Center: Delve into the rich history and cultural heritage of the Amish and Mennonite communities. Just 6 miles from Winesburg, this center offers engaging exhibits and educational resources, enriching your understanding of their traditions.

Things to do recommended for couples

Ready for a romantic getaway in Winesburg? Explore Breitenbach Wine Cellars and Silver Moon Winery for delightful wine tastings amidst charming ambiance. For ultimate relaxation, indulge in a rejuvenating experience at The Spa at Glenmoor, just a short drive away. Enjoy your couple’s retreat.

Things to do recommended for families

Your family will love visiting the Coblentz Chocolate Company for delicious sweets, just 5 miles from Winesburg. Enjoy outdoor fun at Baylor Beach Park, 7 miles away, and unwind at Tuslaw Lions Club Park, 12 miles from town, both offering great spots for relaxation and wellness.

Things to do recommended for groups

In Winesburg, groups can explore the Walnut Creek Amish Flea Market for unique finds, enjoy a family-friendly show at the Amish Country Theater, and experience the charm of Lehman's Hardware, where you can discover a variety of traditional goods just a short drive away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winesburg

If you're traveling with a group, your family, bringing pets, or seeking longer stays, be sure to filter based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winesburg with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winesburg with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, and look for family-friendly amenities, like a private swimming pool. Additionally, being close to attractions that cater to families can make your trip even more enjoyable.
  • Taking your pets with you to Winesburg: For many families, a vacation wouldn't be the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Winesburg: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Winesburg

Winesburg, Ohio, offers a delightful mix of outdoor adventures and family-friendly attractions. Explore the scenic township roads and nearby Holmes County, known for its charming vacation homes and Blessings Cabins. This friendly community invites you to relax and soak in its rich history, making it an ideal destination for travelers seeking both adventure and tranquility. Enjoy the warm atmosphere and friendly people as you discover the beauty of Winesburg and its surroundings.

  • Millersburg: Located 12 miles from Winesburg, Millersburg is a charming city that offers a delightful blend of outdoor adventures and scenic beauty. Known for its recreational areas and vibrant public market, visitors can immerse themselves in local culture while enjoying a variety of activities. Millersburg is also home to beautiful lakes and a national state park, making it ideal for hiking, fishing, and picnicking. The event conference venue adds to its appeal, hosting various community events throughout the year.
  • Berlin: Just 6 miles away from Winesburg, Berlin is a picturesque city that attracts outdoor enthusiasts and adventure seekers alike. Its recreational areas and bustling public market provide a great opportunity to experience the local lifestyle. Berlin is surrounded by stunning landscapes, including a national state park and serene lakes, perfect for outdoor activities such as kayaking and hiking. The charming town neighborhoods offer a unique glimpse into the area’s rich heritage, making it a must-visit destination.
  • Sugarcreek: Situated 8 miles from Winesburg, Sugarcreek is a quaint city known for its beautiful scenery and outdoor pursuits. Here, visitors can explore recreational areas and local markets that showcase handmade goods and fresh produce. The nearby national state park and picturesque lakes offer ample opportunities for hiking and water activities. With its inviting town neighborhoods, Sugarcreek embodies the warmth of small-town America, making it an excellent spot for relaxation and exploration.

Best time to go to Winesburg

If you're planning a trip to Winesburg, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and October, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.0°F (-2.8°C)Light RainMostly CloudySlightly LowAverage
February29.8°F (-1.2°C)Light RainMostly CloudySlightly LowSlightly Low
March39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
April49.8°F (9.9°C)Light RainMostly CloudyAverageSlightly Low
May61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
June68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
July72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
August71.2°F (21.8°C)Light RainMostly SunnyAverageSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October53.6°F (12.0°C)Light RainMostly SunnySlightly HighAverage
November41.4°F (5.2°C)Light RainMostly SunnySlightly LowAverage
December33.4°F (0.8°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Keeping your travel dates flexible can be a great way to take advantage of fluctuating prices. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the total booking amount. Being the planner has its perks. By enrolling in our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up where you left off, and manage your travel arrangements. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Winesburg getaway

Experience the unique character of Winesburg with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Winesburg

Are you hoping to find attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that Winesburg has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • The Legends of Massillon (14.8 mi / 23.8 km)

Exploring the natural landscape of Winesburg

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Winesburg is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation to and around Winesburg

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

Frequently asked questions

What is the best area to stay in Winesburg, Ohio, United States of America when booking a vacation rental?
When considering a stay in Winesburg, Ohio, a great area to explore is the charming neighborhood surrounding the town's center. This area is known for its picturesque landscapes and close-knit community vibe, making it an inviting choice for vacationers. You'll find a selection of cozy vacation rentals that cater to various preferences, often offering a quaint home-away-from-home experience.

While in this neighborhood, you can enjoy the beautiful scenery with a visit to the local parks, great for leisurely strolls or picnics. Additionally, the area is conveniently located near attractions such as historical sites that showcase the rich heritage of Winesburg, giving visitors a glimpse into its past. The town also hosts seasonal events that celebrate local culture, providing a unique opportunity to engage with the community.
How much does it cost to rent a vacation home in Winesburg?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winesburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winesburg vacation house rentals?
You can find great discounts on house rentals in Winesburg on Vrbo, 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.
What is the most popular type of vacation rental accomodation in Winesburg?
In Winesburg, vacation houses and cottages are the most popular types of rentals, with several options available throughout the area. These accommodations often feature cozy interiors, fully equipped kitchens, and inviting living spaces, making them superb for travelers seeking a comfortable home base. Many of these properties are situated in tranquil settings, allowing guests to enjoy the peaceful countryside.
Are there any family house rentals in Winesburg?
In Winesburg, Ohio, there are some family-friendly house rentals available. Visitors can enjoy a tranquil setting with access to nearby attractions that celebrate the charm of rural America. Many of these homes provide spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play safely.

The surrounding area offers opportunities to explore local parks and nature trails, making it ideal for families who appreciate outdoor activities. Additionally, the close-knit community atmosphere is great for those looking to experience a slice of small-town life.
Can I find long-stay vacation rentals in Winesburg?
A long-stay vacation rental in Winesburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winesburg?
In Winesburg, travelers can find several pet-friendly house rentals that cater to those looking to enjoy a rural retreat. Many of these properties offer charming amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families or groups traveling with pets. The peaceful surroundings allow for leisurely walks and relaxation, with plenty of opportunities for outdoor activities.
Are there any remote work vacation rentals in Winesburg?
In Winesburg, Ohio, there are several vacation rentals suitable for remote work. Travelers can expect properties equipped with essential amenities such as free Wi-Fi, allowing for seamless connectivity during their stay. Many rentals also feature comfortable living spaces conducive to productivity, making them ideal for those looking to balance work and leisure. The peaceful rural setting of Winesburg provides a tranquil backdrop, while local attractions, including charming shops and eateries, are just a short drive away, offering a delightful escape during breaks from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winesburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winesburg with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Winesburg?
In Winesburg, popular rental amenities include kitchens, which allow guests to prepare their own meals, as well as decks or patios for enjoying the fresh air and scenic views of the surrounding countryside. Many rentals also feature coffee and tea makers for a convenient morning routine. Dining areas are common, providing spaces for families or friends to gather for meals. Additionally, fireplaces are often included, creating a cozy atmosphere for relaxing after a day of exploring the charming town.
When is the best time to visit Winesburg for a vacation rental?
The best time to visit Winesburg for a vacation rental is during October, when the air is crisp and the vibrant autumn leaves create a picturesque backdrop. This month offers a delightful experience for those who appreciate the charm of small-town Ohio, as the local community often celebrates harvest festivals, showcasing seasonal produce and crafts.

During the peak season from June to August, visitors flock to the area, enjoying warm temperatures ranging from the mid-70s to low 80s Fahrenheit. This period features numerous outdoor activities, including hiking and exploring nearby parks, making it an excellent time for travelers. However, if you prefer a quieter atmosphere with fewer crowds, October provides a wonderful opportunity for leisurely strolls and sightseeing without the hustle and bustle.

For budget-conscious travelers, November marks a low season in Winesburg. While temperatures begin to drop, this transitional month can still offer great experiences, like cozying up in a local café or exploring the quaint shops at a relaxed pace, all while enjoying the community's warm hospitality.

Ultimately, the ideal time to book a vacation rental in Winesburg hinges on your preferences for either vibrant summer activities or the serene beauty of fall.
How early should I book a Winesburg vacation rental?
Book your Winesburg vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winesburg, Ohio, United States of America?
In Winesburg, Ohio, visitors can take part in the quaint charm of this small town, often associated with the works of author Sherwood Anderson. One of the main attractions is the historic downtown area, where you can find local shops and eateries that reflect the community's heritage. The surrounding countryside offers picturesque views and opportunities for outdoor activities, such as hiking and exploring the rural landscape.

Nearby, attractions such as the Amish farms in the region provide great experiences, allowing visitors to appreciate local craftsmanship and traditional lifestyles. The Winesburg area is also close to other small towns in Holmes County, known for their Amish culture, where travelers can enjoy local markets and homemade goods.
Can I change or cancel my Winesburg home rental booking on Vrbo?
To find Winesburg vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winesburg vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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