Winchester vacation rentals

We found 20 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:

  • Kenton Station Golf Course (22.7 mi / 36.5 km)
  • Kinkead Ridge Vineyard and Winery (17.5 mi / 28.1 km)
  • Hillsboro Elks Country Club (17.7 mi / 28.5 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 (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)
  • Fallsville State Wildlife Area (24 mi / 38.5 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, Ohio, United States of America when booking a vacation rental?
When considering a vacation rental in Winchester, Ohio, the area surrounding the downtown district stands out as an excellent choice. This vibrant neighborhood is not only central but also rich in local charm and amenities. Visitors can enjoy attractions like the historic Winchester Depot, which offers a glimpse into the town's railway heritage, and the picturesque parks nearby, great for relaxing walks or family picnics.

Another appealing option is the vicinity of the scenic Paint Creek, where nature enthusiasts can indulge in outdoor activities like hiking and fishing. The neighborhoods here often feature a variety of vacation rental properties, from cozy cottages to larger homes, giving travelers plenty of options to suit their needs.
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 in the area. These cabins are typically situated in serene, wooded settings, providing a rustic and tranquil experience for travelers. Most cabins come equipped with essential amenities such as fully stocked kitchens, cozy living areas, and often outdoor decks or porches for enjoying the natural surroundings. This makes them ideal for families or groups seeking a getaway that combines comfort with the beauty of nature.
Are there any family house rentals in Winchester?
In Winchester, Ohio, there are several family-friendly house rentals available, making it a suitable destination for groups traveling together. The homes typically offer spacious living areas, full kitchens for preparing meals, and outdoor spaces where children can play and families can gather. Many properties come equipped with amenities like Wi-Fi and air conditioning to ensure a comfortable stay.

Visitors will appreciate the town's charm, with nearby parks and local attractions providing opportunities for outdoor activities and family fun. See all family-friendly rentals in Winchester.
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 those traveling with furry companions. These rentals typically offer a range of amenities including spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. Many properties are situated in quiet neighborhoods, providing a peaceful atmosphere for both guests and their pets.

While exploring the area, visitors can take advantage of nearby parks and walking trails that are superb for outdoor activities with pets.
Are there any remote work vacation rentals in Winchester?
In Winchester, Ohio, there are several vacation rentals suitable for remote work. These properties offer essential amenities such as free Wi-Fi in rooms and public areas, ensuring that guests can stay connected and productive during their stay. Additionally, many rentals are equipped with comfortable workspaces, allowing for a conducive environment for remote 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 kitchens, which allow travelers to prepare their own meals, and cozy fireplaces that create a warm atmosphere during colder months. Many rentals also feature decks or patios, providing outdoor space for relaxation and enjoying the surroundings. Families will appreciate the availability of children's books in some properties, adding a thoughtful touch for younger guests. Additionally, blenders are often available, great for making smoothies or other beverages during a stay.
When is the best time to visit Winchester for a vacation rental?
September is the most popular time to visit Winchester, Ohio, as the summer crowds begin to thin and the weather remains pleasantly warm. The peak season spans from July to September, attracting families and outdoor enthusiasts eager to explore the region's parks and local events. During this vibrant period, you can join in on various festivals and enjoy the beautiful scenery, making it an ideal time for sightseeing and outdoor activities.

In September, temperatures typically range from the mid-50s to the low 80s Fahrenheit, providing a comfortable climate for hiking, biking, or simply relaxing in the lush landscapes. The stunning fall foliage begins to emerge towards the end of the month, offering a picturesque backdrop for outdoor adventures or leisurely strolls through Winchester's charming streets.

For travelers looking for more budget-friendly options, December presents an excellent opportunity. While it is the low season, the holiday spirit brings unique local events and a quieter atmosphere, superb for those who appreciate a peaceful getaway during the festive season.

Ultimately, your choice of when to visit Winchester depends on whether you prefer the lively energy of the peak summer months or the tranquil beauty of early fall and beyond.
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, Ohio, United States of America?
In Winchester, Ohio, visitors can explore a variety of attractions that reflect the area's rich history and natural beauty. The Winchester Historical Society offers insights into the local heritage, showcasing artifacts and exhibits that tell the story of the town's development. Nearby, the scenic Paint Creek State Park provides opportunities for outdoor activities such as hiking, fishing, and picnicking, making it a great spot for nature enthusiasts.

Additionally, the charming downtown area features local shops and eateries that highlight the community's character. For those interested in agriculture and rural life, the surrounding countryside offers picturesque views and seasonal activities, including farmers' markets and festivals.
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 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 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.
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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