Castellina in Chianti vacation rentals

We found 2,523 vacation rentals — enter your dates for availability

Discover a selection of 83 homes, 62 apartments, and other vacation rentals in Castellina in Chianti that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Castellina in Chianti

Showing deals for:Dec 19 - Dec 26

Image gallery for "Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

Pool
10 out of 10 rating
Exceptional
(11 reviews)

"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

Siena, Tuscany

5% off
Price is $680
$4,760 for 7 nights
All fees included
"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

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Find out more about Castellina in Chianti

Find out more about Castellina in Chianti

Why visit Castellina in Chianti

  • Romantic Getaway: Castellina in Chianti is the perfect setting for couples, offering enchanting views and intimate experiences.
  • Historic Exploration: Discover charming churches, picturesque piazzas, and ancient castles that showcase the town's rich history.
  • Scenic Beauty: Enjoy the breathtaking landscapes of the Chianti Hills, ideal for outdoor activities and relaxation.
  • Local Wine Indulgence: Savor the region's renowned wines, making for a delightful culinary experience.
  • Diverse Accommodations: Choose from cozy apartments to luxurious villas, ensuring a comfortable stay tailored to your needs.

Popular types of accommodation in Castellina in Chianti

Discover the charm of Castellina in Chianti with a variety of vacation rentals to suit every traveler. Whether you're looking for cozy apartments, spacious villas, or houses, we have it all. Our Chianti vacation villa rentals offer the perfect base for exploring this stunning region. Choose the ideal vacation rental in Castellina in Chianti and enjoy a memorable getaway filled with transparency, savings, and reassurance.

  • Apartments: The top choice for vacation rentals in Castellina in Chianti, offering comfortable living spaces with convenient amenities.
  • Villas: A popular selection, these spacious properties provide a luxurious stay with beautiful surroundings.
  • Houses: Ideal for families or groups, these homes offer a home-like atmosphere with privacy.
  • Caravan Parks: A unique accommodation option, perfect for those who enjoy a more adventurous and outdoor experience.
  • Cottages: Cozy and charming, these quaint lodgings are perfect for a romantic getaway or peaceful retreat.**

Top attractions near Castellina in Chianti

Castellina in Chianti is perfect for a romantic and outdoor vacation, offering a blend of culture and entertainment. Explore local attractions like charming churches, picturesque piazzas, and historic castles. Don't miss the stunning Chianti Hills or take the time to delve into the beauty of Castellina itself. Whether you're seeking a romantic getaway or a cultural experience, there's plenty to discover in and around this enchanting Tuscan town.

  • Monteriggioni Castle: A well-preserved medieval fortress located 6 miles from Castellina in Chianti, Monteriggioni Castle boasts stunning views and rich history. Explore its ancient walls and enjoy the cultural ambiance of this charming village.
  • Piazza del Campo: Situated 11 miles away, Piazza del Campo is a vibrant square known for its unique shell shape and lively atmosphere. It hosts the famous Palio horse race and is surrounded by historic buildings and cafes.
  • Siena Cathedral: Also located 11 miles from Castellina, Siena Cathedral is a magnificent example of Gothic architecture. Marvel at its intricate façade and stunning artworks while soaking in the rich cultural heritage of Siena.

Things to do recommended for couples

For a romantic getaway in Castellina in Chianti, visit Il Molino di Grace Winery, just 4 miles away, or Isole e Olena Winery, 3 miles down the road. Don’t miss Buondonno Winery, located right in Castellina. Each offers enchanting vibes perfect for couples.

Things to do recommended for families

Your family vacation in Castellina in Chianti will be filled with excitement. Enjoy thrilling karting at the Siena Circuit, catch a game at the nearby Siena Stadium, or visit the historic Stadio Artemio Franchi—perfect for sports enthusiasts of all ages.

Things to do recommended for groups

Groups visiting Castellina in Chianti can hike the scenic Sentierelsa Trail, just 8 miles away, or indulge in shopping at The Mall Luxury Outlet, 18 miles from town. Don't miss a visit to Ra-Ma snc, a charming local store located nearby for unique finds.

*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 Castellina in Chianti

When planning your trip, whether you're traveling in a group, with family, bringing along pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Castellina in Chianti with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Castellina in Chianti with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Castellina in Chianti: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Castellina in Chianti: If you're searching for 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 preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Castellina in Chianti

Castellina in Chianti is a charming destination perfect for a romantic getaway or an outdoor adventure. Nestled in the heart of Tuscany, this city offers a relaxing atmosphere surrounded by stunning scenery and historical landmarks. Explore the picturesque Chianti area, indulge in local wines, and bask in the luxury of Tuscany's serene vibe. Whether you're seeking tranquility or entertainment, Castellina in Chianti promises an unforgettable holiday experience.

  • Fonterutoli: Nestled in the picturesque hills of Castellina in Chianti, Fonterutoli is a charming village that beckons travelers seeking a romantic and outdoor experience. The area is renowned for its stunning landscapes and historic architecture. Visitors can indulge in guided tours that explore the rich history and beauty of the region. Nearby, you'll find significant historic buildings and sites that offer a glimpse into the past. Fonterutoli is the perfect base for wine lovers, with many vineyards and wineries just a stone's throw away.
  • Lilliano: Lilliano enchants visitors with its cultural and romantic allure. This quaint village is a haven for those interested in history and the arts, featuring local museums and historic venues that showcase the region's rich heritage. The vibrant atmosphere is ideal for entertainment-themed activities, with numerous events and conferences held throughout the year. Strolling through Lilliano, you can savor the charm of its historic buildings while enjoying the warm hospitality of the locals.
  • Sicelle: Situated in the heart of Chianti, Sicelle offers a delightful mix of romantic and outdoor experiences. The village is known for its lively piazza, where visitors can relax and soak in the scenic beauty. Adventurous travelers can partake in various sports and swimming activities, making it an excellent spot for those who enjoy being active. The nearby squares are perfect for leisurely walks and mingling with locals, ensuring a memorable vacation immersed in the culture of Tuscany.

Best time to go to Castellina in Chianti

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageSlightly Low
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnySlightly HighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can really pay off, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the organizer truly has its advantages. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up now and begin your earning journey.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area for you to plan new trips, refine your existing plans, or manage your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Rustic Castellina in Chianti will entice you

Enjoy the wineries and other features of Castellina in Chianti. This relaxing city allures visitors with its forests and bird watching. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Castellina in Chianti

Are you searching for attractions to visit in the city? Venture out of your vacation home and check out everything that Castellina in Chianti has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Isole e Olena Winery (3.5 mi / 5.6 km)
  • Il Molino di Grace Winery (3.7 mi / 6 km)
  • Buondonno Winery (3.9 mi / 6.3 km)
  • Castello di Radda Winery (4.5 mi / 7.3 km)
  • Borgo di Vescine - Tenute di Castelvecchi (4.6 mi / 7.4 km)
  • Casa Sola - Chianti Winery (4.7 mi / 7.5 km)

Exploring the natural landscape of Castellina in Chianti

Whether you're an active traveler or just want to appreciate the scenery, Castellina in Chianti is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Chianti Sculpture Park (7.3 mi / 11.7 km)
  • Sentierelsa Trail (8.4 mi / 13.6 km)
  • Alta Val d'Elsa River Park (9.5 mi / 15.3 km)
  • Boboli Gardens (20.2 mi / 32.5 km)
  • Arno River (20.4 mi / 32.8 km)
  • Le Caldane Thermal Baths (9.4 mi / 15.1 km)

Traveling to and around Castellina in Chianti

Fly into Florence Airport, Peretola (FLR), the closest airport, located 23.2 mi (37.4 km) from the city center.

Frequently asked questions

What is the best area to stay in Castellina In Chianti when booking a vacation rental?
When planning a vacation rental in Castellina in Chianti, one of the best areas to consider is the historic center. This charming neighborhood is characterized by its narrow, winding streets and beautiful medieval architecture. Staying here puts you in close proximity to top attractions like the Church of San Salvatore and the impressive Fortress of Castellina, both of which offer a glimpse into the town's rich history. The historic center is also dotted with delightful restaurants and local shops, allowing you to fully immerse yourself in the Tuscan lifestyle.

Another excellent area is the surrounding countryside, where you'll find a variety of charming farmhouses and villas. This area offers stunning views of the Chianti landscape and easy access to outdoor activities like hiking and wine tasting. It's also a short drive from top wineries and olive oil producers, making it superb for those looking to explore the region's gastronomic delights.
How much does it cost to rent a vacation home in Castellina In Chianti?
Prices for vacation rentals in Castellina In Chianti 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 Castellina In Chianti 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 Castellina In Chianti vacation house rentals?
You can find great discounts on house rentals in Castellina In Chianti 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 Castellina In Chianti?
In Castellina In Chianti, villas are the most popular type of vacation rental, with around 80 available throughout this picturesque region of Tuscany. These villas typically feature beautiful outdoor spaces, including gardens and often private swimming pools, great for soaking in the stunning countryside views. Inside, travelers can expect spacious layouts with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups.

Apartments also hold a significant presence, with about 56 options available, often located in charming settings close to local shops and restaurants. These apartments usually come with essential amenities like kitchen facilities and living spaces, offering a comfortable home base for exploring the surrounding vineyards and historical sites.

For those seeking a more traditional experience, there are around 54 vacation houses available, which provide a similar feel to villas but might be more modest in size. Lastly, about 10 cottages can be found, offering a quaint and rustic option for travelers looking to immerse themselves in the tranquil Tuscan landscape.
Are there any family house rentals in Castellina In Chianti?
In Castellina In Chianti, Tuscany, families will find a wide selection of rentals, with approximately 122 options available. This picturesque area is known for its stunning landscapes and rich history, making it an excellent choice for family vacations. Many of the homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor terraces great for enjoying the beautiful Tuscan weather.

Visitors can look forward to amenities such as private pools, game rooms, and large gardens where children can play freely. The locale is surrounded by charming vineyards and olive groves, providing opportunities for wine tasting and exploring local culinary delights. Additionally, nearby attractions like the historic town of Radda in Chianti and the beautiful Chianti Classico wine region are easily accessible, making it convenient for families to experience both relaxation and adventure during their stay.
Can I rent a vacation home with a pool or hot tub in Castellina In Chianti?
In Castellina In Chianti, there are many vacation homes available for rent that feature pools and hot tubs, with around 175 options to choose from. This picturesque region in Tuscany is renowned for its stunning landscapes, vineyards, and charming villages. Travelers can find properties located among the rolling hills, offering breathtaking views and a serene atmosphere.

Many of these rentals come equipped with private pools, inviting hot tubs, and outdoor spaces that are great for relaxation and enjoying the beautiful Tuscan weather. Expect amenities such as fully equipped kitchens for preparing local delicacies, spacious living areas, and sometimes even alfresco dining options. Some properties may also feature traditional Tuscan architecture, adding to the overall charm of the stay.
Can I find long-stay vacation rentals in Castellina In Chianti?
A long-stay vacation rental in Castellina In Chianti 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 Castellina In Chianti?
In Castellina In Chianti, travelers will find a variety of pet-friendly house rentals, with around 114 options available. This charming area in Tuscany is renowned for its picturesque landscapes, vineyards, and historic architecture. Many vacation rentals here offer amenities such as fully equipped kitchens, outdoor terraces, and swimming pools, providing a comfortable and friendly space for both pets and their owners.

The region is dotted with beautiful countryside trails, superb for walking dogs and exploring the stunning Chianti hills. Additionally, nearby towns offer pet-friendly cafes and restaurants, allowing visitors to enjoy local cuisine while accommodating their furry companions.
Are there any remote work vacation rentals in Castellina In Chianti?
In Castellina In Chianti, there are plenty of remote work vacation rentals available, with approximately 187 properties suiting this need. This beautiful region of Tuscany is not only known for its stunning landscapes and vineyards but also provides a conducive environment for remote working. Many rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces featuring desks and comfortable chairs, and sometimes even office setups with monitors.

Travelers can expect properties that allow for a productive work experience while also enjoying the tranquility of the countryside. Some homes may offer additional amenities like outdoor terraces for fresh air breaks, cozy living areas for relaxation, and fully equipped kitchens for convenient meal preparation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Castellina In Chianti vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Castellina In Chianti 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 Castellina In Chianti?
In Castellina In Chianti, popular vacation rental amenities include WiFi, kitchens, and pools, with options for both private and shared pools. Many rentals are set in picturesque surroundings, offering a blend of rustic charm and modern comforts. Travelers can expect spacious living areas, outdoor terraces for enjoying the beautiful Tuscan landscape, and well-equipped kitchens ideal for preparing local cuisine.
When is the best time to visit Castellina In Chianti for a vacation rental?
The most popular time to visit Castellina In Chianti is during the summer months, particularly July. This period marks the peak season, drawing travelers who are eager to immerse themselves in the stunning Tuscan landscape, enjoy local festivals, and indulge in the region's exquisite wines and culinary delights. With warm temperatures often ranging from the mid-70s to low 90s Fahrenheit, it's an ideal time for outdoor activities such as vineyard tours, hiking through the picturesque countryside, and savoring al fresco dining experiences.

From July to September, the charming streets of Castellina In Chianti come alive with vibrant markets and cultural events, making it an exciting time for those seeking a lively atmosphere. Moreover, the long days provide ample opportunity for sightseeing, whether you're exploring historic castles or enjoying scenic drives through the rolling hills dotted with vineyards.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter and more intimate experience, great for travelers who appreciate the beauty of Tuscany's autumn foliage and the opportunity to engage with the local culture without the summer crowds. The cooler temperatures, typically in the mid-50s to low 60s Fahrenheit, create a cozy atmosphere ideal for enjoying local harvest festivals and wine tastings.

Ultimately, the best time to visit Castellina In Chianti really depends on your travel preferences—whether you're drawn to the vibrant summer energy or the serene charm of the fall season.
How early should I book a Castellina In Chianti vacation rental?
Book your Castellina In Chianti 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 Castellina In Chianti?
In Castellina in Chianti, visitors can experience firsthand the enchanting Tuscan countryside, where charming vacation rentals are often surrounded by vineyards and olive groves. The town itself boasts historical attractions such as the impressive Castello di Castellina, which offers insights into the area's medieval past.

Exploring the picturesque streets, travelers can discover local artisan shops and enjoy authentic Tuscan cuisine at quaint trattorias. The nearby Chianti Classico wine region is famous for its vineyards, making it a great base for wine tours and tastings.

For those interested in nature, the surrounding hills provide numerous hiking and biking trails, offering breathtaking views of the landscape.
Can I change or cancel my Castellina In Chianti home rental booking on Vrbo?
To find Castellina In Chianti 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 Castellina In Chianti 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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