Winchester vacation rentals

We found 18 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Winchester to find one that's perfect for your trip. Vacation homes offer the amenities you expect for your family, friends, or furry companion, like cable TV and a washer and dryer. At the end of the day, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.
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Find out more about Winchester

Why visit Winchester

  • Outdoor Adventures: Winchester offers a range of outdoor activities, perfect for nature lovers and thrill-seekers.
  • Historic Attractions: Explore historic houses and archaeological sites that showcase the rich history of the area.
  • Charming Downtown: Stroll through the quaint downtown filled with unique shops and local amenities.
  • Welcoming Neighborhoods: Enjoy the friendly atmosphere in neighborhoods like Oakland, ideal for relaxation and exploration.
  • Diverse Accommodations: Choose from cozy cabins and spacious homes that cater to families and romantic getaways.

Popular types of accommodation in Winchester

When it comes to vacation rentals in Winchester, you'll find a variety of options to suit your needs. Popular choices include cozy cabins, spacious houses, and unique agritourism stays. Many of these accommodations offer generous room sizes, laundry facilities, and the comfort of a lovely stay. Whether you're looking for the ideal family getaway or a peaceful retreat, our Winchester travel guide has the perfect options for you.

  • Cabins: These rustic retreats are the top choice for visitors to Winchester, offering a peaceful escape surrounded by nature.
  • Houses: Ideal for families or groups, these homes provide the comforts of home with added privacy.
  • Agritourism: Experience farm life firsthand with unique stays that connect you to the countryside and its charm.
  • Cottages: Quaint and cozy, these accommodations are perfect for a romantic getaway or peaceful retreat.
  • Condos: Offering modern amenities, condos are a great option for those seeking convenience during their stay.**

Top attractions near Winchester

Winchester, Ohio, is perfect for outdoor enthusiasts and adventure seekers, offering a blend of scenic beauty and rich history. Visitors can explore historic houses, archaeological sites, and national state parks, making it an ideal destination for families and culture lovers alike. Whether you're seeking thrilling adventures or a glimpse into the past, Winchester has something for everyone to enjoy.

  • Serpent Mound: An impressive ancient effigy mound, Serpent Mound is steeped in Native American history and culture. The unique serpent shape provides a fascinating glimpse into prehistoric beliefs and is surrounded by picturesque landscapes.
  • Adams Lake State Park: Perfect for outdoor enthusiasts, this park offers stunning scenery and a range of activities like fishing, hiking, and picnicking. Enjoy the serene lake views and abundant wildlife in this natural haven.
  • Grant Boyhood Home: Step back in time at this historic house, where Ulysses S. Grant spent his formative years. Explore the site’s rich history and learn about the early life of the 18th President of the United States.

Things to do recommended for couples

For a romantic getaway in Winchester, explore Meranda-Nixon Winery, just 12 miles away, for its charming atmosphere and entertainment vibes. Alternatively, visit Kinkead Ridge Vineyard and Winery, located 17 miles from Winchester, where you can savor exquisite wines amidst a picturesque setting.

Things to do recommended for families

Families visiting Winchester, Ohio can explore the charming local parks, enjoy a fun day at the nearby playgrounds, and take part in seasonal festivals that offer activities for kids and adults alike. Don’t miss the local farms for fresh produce and family-friendly events.

Things to do recommended for groups

Experience a round of golf at the Hillsboro Elks Country Club, located 18 miles from Winchester. Enjoy the outdoor atmosphere and engage in friendly competition with your group while taking in the beautiful surroundings.

*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 Winchester

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily sort through these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winchester: For many, a family vacation isn't truly fulfilled without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Winchester

Winchester, Ohio offers a delightful blend of outdoor adventures and scenic beauty, perfect for a family getaway or a romantic excursion. Explore the historic downtown area, filled with charming shops and local amenities. Nearby neighborhoods, like the Oakland area, provide a welcoming atmosphere with friendly people and rich history, making it an ideal destination for travelers seeking both relaxation and adventure.

  • Seaman: Located a mere 4 miles from Winchester, Seaman is a charming city known for its outdoor adventures and stunning scenery. Visitors flock to this picturesque locale to enjoy recreational areas, campgrounds, and hiking trails that showcase the natural beauty of the region. Seaman is also home to notable landmarks, including historic sites and archaeological wonders, as well as access to a national state park. Whether you’re seeking a day of exploration or a weekend of camping under the stars, Seaman promises an invigorating experience for all outdoor enthusiasts.
  • West Union: Situated 12 miles from Winchester, West Union offers an exhilarating blend of adventure and scenic landscapes. This vibrant city is a gateway to recreational areas, campgrounds, and hiking trails, making it an ideal destination for nature lovers. West Union is also surrounded by captivating attractions, including a national state park, serene lakes, and intriguing historic sites. With its rich outdoor offerings, West Union is perfect for those looking to immerse themselves in nature while enjoying a variety of activities.
  • Cherry Fork: Nestled within the vicinity of Winchester, Cherry Fork is a quaint village that provides a unique blend of family-friendly and business-themed experiences. Visitors can explore local shopping centers and malls, making it a great spot for leisurely shopping trips or quick business meetings. The welcoming atmosphere and community spirit make Cherry Fork an inviting stop for tourists looking to enjoy a slice of small-town charm while still having access to essential amenities.

Best time to go to Winchester

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.1°F (-0.5°C)Light RainMostly CloudySlightly LowSlightly Low
February34.5°F (1.4°C)Light RainMostly CloudySlightly LowSlightly Low
March43.9°F (6.6°C)Light RainMostly CloudyAverageSlightly Low
April53.6°F (12.0°C)Light RainMostly SunnySlightly HighAverage
May63.5°F (17.5°C)Light RainMostly SunnyAverageAverage
June71.2°F (21.8°C)Light RainMostly SunnyAverageSlightly High
July74.7°F (23.7°C)Light RainMostly SunnySlightly HighSlightly High
August73.2°F (22.9°C)Light RainMostly SunnyAverageSlightly High
September67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
October56.1°F (13.4°C)Light RainMostly SunnyAverageAverage
November44.1°F (6.7°C)Light RainMostly SunnyAverageAverage
December37.2°F (2.9°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can lead to great deals since prices often fluctuate. Additionally, consider booking a longer stay to take advantage of even bigger savings. To discover a Vrbo property that aligns with your budget, make use of our filters to sort by price, location, and rental type. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on your total booking amount. It truly benefits you to take on the planning role. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

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

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Winchester

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winchester a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hillsboro Elks Country Club (17.7 mi / 28.5 km)
  • Kinkead Ridge Vineyard and Winery (17.5 mi / 28.1 km)
  • Kenton Station Golf Course (22.7 mi / 36.5 km)
  • Meranda-Nixon Winery (12.4 mi / 20 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Winchester is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Rocky Fork Lake State Park (18.2 mi / 29.3 km)
  • Rocky Fork Lake (19.5 mi / 31.3 km)
  • Brush Creek State Forest (23.6 mi / 37.9 km)
  • Ripley Lions Club Community Park (17.2 mi / 27.7 km)
  • Colonel Higgins Park (20 mi / 32.1 km)
  • Augusta River Park (21.8 mi / 35.2 km)

Traveling to and around Winchester

The nearest airport is in Cincinnati, OH (LUK-Cincinnati Municipal - Lunken Field), located 43.2 mi (69.6 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Cincinnati-Northern Kentucky Int'l Airport (CVG), which is 54.6 mi (87.9 km) away.

Frequently asked questions

What is the best area to stay in Winchester when booking a vacation rental?
When considering a vacation rental in Winchester, Ohio, the downtown area is a fantastic choice. This charming neighborhood offers a quaint atmosphere with easy access to local shops and eateries, making it superb for those looking to immerse themselves in the community. One of the great attractions nearby is the historic Winchester Village, where you can explore unique architecture and enjoy the local culture. Additionally, the nearby Adams Lake State Park provides opportunities for outdoor activities such as hiking, fishing, and picnicking, adding to the area's appeal.

Another great option is the area surrounding the scenic Adams County Winery, where visitors can enjoy wine tastings and picturesque vineyard views. Staying in this vicinity gives you a taste of rural Ohio while being close to nature and local craftsmanship.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation rentals in Winchester 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 Winchester 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 Winchester vacation house rentals?
You can find great discounts on house rentals in Winchester 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 Winchester?
In Winchester, cabins are the most popular type of vacation rental, with several available throughout the area. These cabins are typically located in serene, wooded settings, offering a peaceful escape for travelers. Most feature cozy interiors, full kitchens for preparing meals, and outdoor spaces like decks or porches to enjoy the natural surroundings. These accommodations are ideal for families or groups seeking a relaxing retreat.
Are there any family house rentals in Winchester?
In Winchester, Ohio, there are several family-friendly house rentals available. The town's welcoming atmosphere and proximity to natural attractions make it an excellent choice for families. Many of these homes provide spacious living areas, full kitchens for preparing meals, and outdoor spaces great for children to play and enjoy the fresh air.

Visitors can explore local parks and enjoy outdoor activities, as well as take advantage of nearby amenities such as grocery stores and restaurants.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester 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 Winchester?
In Winchester, Ohio, there are several pet-friendly house rentals available for travelers. These properties typically offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. Many rentals also feature fenced yards, ensuring a safe environment for pets to roam.

The surrounding area provides opportunities for outdoor activities, including nearby parks and trails that are suitable for walks with pets.
Are there any remote work vacation rentals in Winchester?
In Winchester, Ohio, there are several vacation rentals suitable for remote work. Many of these properties provide comfortable workspaces, reliable internet access, and quiet environments that are conducive to productivity. Travelers can expect amenities such as fully equipped kitchens for meal preparation, spacious living areas for relaxation, and outdoor spaces to enjoy fresh air during breaks. The town offers a charming small-town atmosphere, with local parks and recreational areas nearby, great for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester 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 Winchester?
In Winchester, popular vacation rental amenities include WiFi, which allows guests to stay connected during their stay. Rentals often feature well-equipped kitchens and kitchen islands, making it easy for travelers to prepare their own meals. Additionally, many properties provide a selection of children's books, suiting families with young kids.
When is the best time to visit Winchester for a vacation rental?
September is the most popular time to visit Winchester, Ohio, drawing travelers eager to experience the charming atmosphere of this quaint town. The peak season spans from July to September, when warm weather and vibrant community events bring the area to life. During these months, visitors can partake in outdoor activities like exploring the scenic parks and enjoying local festivals that celebrate the region's culture.

In September, temperatures typically range from the low 50s to the mid-70s Fahrenheit, creating a comfortable climate for leisurely strolls through the town or hiking along nearby trails. The pleasant weather and beautiful fall foliage make it an ideal time for sightseeing and outdoor adventures, allowing travelers to immerse themselves in Winchester's natural beauty.

For those seeking budget-friendly options, December offers a quieter experience with lower vacation rental rates. This time of year features cozy holiday festivities and opportunities for peaceful exploration, making it a wonderful choice for those looking to unwind and enjoy the charm of Winchester without the crowds.

Ultimately, the best time to visit Winchester for a vacation rental depends on your interests.
How early should I book a Winchester vacation rental?
Book your Winchester 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 Winchester?
In Winchester, Ohio, visitors can explore several attractions that highlight the area's natural beauty and small-town charm. The nearby Paint Creek State Park offers opportunities for hiking, fishing, and camping, making it a great destination for outdoor enthusiasts. The park features scenic trails and picturesque views of the creek, ideal for those looking to connect with nature.

The historic downtown area of Winchester is also great, where travelers can stroll along the quaint streets, visit local shops, and enjoy community events that often take place in the town square. For those interested in local history, the Winchester Community Historical Society provides insights into the town's past and its significance in the region.

If you enjoy scenic drives, the surrounding countryside is dotted with beautiful landscapes and farmland, superb for a leisurely exploration.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winchester 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.

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