Winchester vacation rentals

We found 19 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.

Find spaces that suit your style

  • 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, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winchester

Why visit Winchester

  1. Outdoor Adventures: Experience the thrill of hiking and exploring scenic national parks and archaeological sites.
  2. Historic Exploration: Visit charming historic houses that showcase Winchester's rich heritage and culture.
  3. Vibrant Downtown: Stroll through downtown Winchester, filled with trendy cafes and local shops for unique finds.
  4. Diverse Accommodations: Choose from cozy cabins, charming cottages, and spacious vacation homes tailored to your needs.
  5. Day Trip Opportunities: Take advantage of nearby attractions for memorable day trips that enhance your visit.

Popular types of accommodation in Winchester

If you're exploring vacation rentals in Winchester, you're in for a treat! Our most popular types of accommodation include cozy cabins, charming cottages, and spacious houses. Whether you're searching for Winchester vacation home rentals or looking to unwind in a Winchester cottage, we provide the perfect options for your getaway. Enjoy your stay with confidence, knowing you have a range of comfortable choices tailored to your needs.

  • Cabins: The top choice for vacation rentals in Winchester, offering a rustic escape surrounded by nature.
  • Houses: A popular option for groups or families, providing the comforts of home during your stay.
  • Cottages: A delightful option for those seeking a quaint and cozy atmosphere for their getaway.
  • Apartments: A convenient choice for solo travellers or couples, providing a home-like experience.
  • Condos: Ideal for those wanting a modern space with amenities, perfect for a relaxing vacation.**

Top attractions in Winchester

Winchester, Ohio, is perfect for outdoor enthusiasts and adventure seekers, featuring attractions like archaeological sites, historic houses, and national parks. Visitors can immerse themselves in the local culture while exploring scenic landscapes. For a memorable experience, consider day trips from Winchester to discover even more of the region's charm and beauty.

  1. Serpent Mound: This fascinating archaeological site, located 20.9km from Winchester, features a unique effigy mound shaped like a serpent. It offers a deep dive into ancient cultures and their beliefs, providing an enriching experience surrounded by lush landscapes.
  2. Adams Lake State Park: Just 17.7km away, this national park is perfect for outdoor enthusiasts. Explore scenic trails, enjoy fishing, or have a picnic while soaking in the natural beauty and adventure that the park has to offer.
  3. Grant Boyhood Home: Located 24.1km from Winchester, this historic house showcases the early life of Ulysses S. Grant. Visitors can immerse themselves in history and culture, learning about the significant events that shaped this iconic figure's life.

Things to do recommended for couples

For a romantic getaway in Winchester, explore Meranda-Nixon Winery, just 19.3km away, where you can enjoy a lovely atmosphere and entertainment. Alternatively, visit Kinkead Ridge Vineyard and Winery, 27.4km from town, for delightful wine tasting and a charming setting perfect for couples.

Things to do recommended for groups

Groups visiting Winchester can enjoy a round of golf at Hillsboro Elks Country Club, located 29.0km away. The club offers a relaxed outdoor atmosphere, perfect for bonding while enjoying the sport and the scenic views of the countryside.

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

When planning your trip—whether you're travelling with a group, your family, your pets, or seeking extended stays—be sure to refine your search based on your top priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young children can present its own set of challenges. 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 families, a vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, we invite you to explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer amenities such as feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals offering 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winchester

Winchester, Ohio, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a memorable vacation. From family-friendly parks to romantic spots, the city and its nearby neighborhoods provide an array of accommodations to suit every traveller's needs. Explore the vibrant downtown Winchester, where trendy cafes and local shops await, ensuring a perfect getaway experience in this charming region. Embrace the essence of Winchester and discover its unique atmosphere on your journey.

  • Seaman: Located a mere 6.4km from Winchester, Seaman is a welcoming city that invites outdoor enthusiasts and adventure seekers. This charming locale is known for its stunning scenery and recreational opportunities. Visitors can enjoy the local campground, explore picturesque hiking trails, and immerse themselves in the natural beauty of the area. Notable attractions nearby include historic sites and archaeological wonders, as well as the expansive national state park, making Seaman a delightful stop for those looking to connect with nature and history.
  • Peebles: Situated 20.9km from Winchester, Peebles is another gem for travellers seeking outdoor adventures. The city boasts beautiful recreational areas, campgrounds, and an array of hiking trails that showcase its scenic landscapes. The proximity to a national state park, along with fascinating historic and archaeological sites, makes Peebles an excellent choice for exploration and discovery. Whether you're hiking through lush greenery or soaking in the local history, Peebles offers a refreshing getaway for nature lovers.
  • West Union: Just 19.3km from Winchester, West Union is a vibrant city that captivates visitors with its outdoor experiences and scenic beauty. The area is perfect for adventure seekers, featuring recreational areas, campgrounds, and an enticing network of hiking trails. Nature enthusiasts will appreciate the nearby national state park, picturesque lakes, and rich historical landmarks. West Union combines the thrill of outdoor activities with the charm of local history, making it an ideal destination for those looking to unwind and explore.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform to plan new trips, keep your travel arrangements on track, or review and organize your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for your ease of access. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/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:

  • Kinkead Ridge Vineyard and Winery (17.5 mi / 28.1 km)
  • Hillsboro Elks Country Club (17.7 mi / 28.5 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, a popular area to stay is near the charming downtown district. This area offers a delightful blend of local shops, restaurants, and cafes, making it easy to immerse yourself in the community's atmosphere. Staying in this part of town places you within walking distance of several top attractions, such as the historic Winchester Public Library, which boasts beautiful architecture and a welcoming environment for visitors. Additionally, the nearby Adams Lake State Park provides an excellent opportunity for outdoor enthusiasts, with its scenic views and recreational activities.
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 travelling 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.
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 typically offer a rustic charm and a comfortable atmosphere, featuring amenities such as fully equipped kitchens, cosy living areas, and often outdoor spaces like decks or porches for enjoying the surrounding nature. Many are situated near scenic spots, allowing guests to immerse themselves in the local landscape.
Are there any family house rentals in Winchester?
In Winchester, Ohio, there are some family-friendly house rentals available for those looking to enjoy a comfortable stay. The area offers a variety of properties that cater to families, often featuring spacious living rooms, full kitchens for preparing meals, and outdoor spaces for children to play. Visitors can expect amenities such as Wi-Fi and ample parking, ensuring a straightforward experience.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winchester?
In Winchester, Ohio, there are several pet-friendly house rentals available, providing a welcoming environment for those travelling with pets. Many of these properties feature amenities such as fenced yards, which are ideal for letting pets roam safely, along with spacious living areas and fully equipped kitchens for a comfortable stay.
Are there any remote work vacation rentals in Winchester?
In Winchester, Ohio, there are several vacation rentals that cater to remote workers. Many of these properties provide a suitable environment for productivity, featuring dedicated workspaces, high-speed internet, and comfortable seating arrangements. Travellers can expect amenities such as fully equipped kitchens, which allow for convenient meal preparation, as well as relaxing living areas to unwind 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 travellers 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.
When is the best time to visit Winchester for a vacation rental?
September is the most popular time to visit Winchester, Ohio, as it marks the transition into autumn and offers an array of outdoor activities that appeal to adventure seekers and families alike. The peak season spans from July to September, when travellers flock to enjoy the warm summer days, vibrant local festivals, and the beautiful scenery of the surrounding countryside. During this time, temperatures generally hover in the mid to high 20s Celsius, making it superb for hiking, cycling, and exploring the charming town.

For those considering a visit, September gives you the advantage of pleasant weather without the peak summer crowds. The days are still warm, but you'll find a more relaxed atmosphere, ideal for enjoying leisurely strolls through parks or visiting local farmers' markets. The changing colours of the leaves as autumn approaches also provide a stunning backdrop for any outdoor activities or sightseeing.

If you're looking for a more budget-friendly option, December is a great time to visit Winchester. This month offers a unique charm with festive vacation decorations and local events that capture the spirit of the season. It's cooler, with temperatures dipping to around 0 to 5 degrees Celsius, the town has a cozy feel that makes it superb for enjoying hot cocoa by a fireplace or exploring local shops.
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.
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 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 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, Vrbo 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 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More Vacation Ideas