Castellina in Chianti vacation rentals

We found 2,516 vacation rentals — enter your dates for availability

Discover a selection of 27 homes, 26 villas, and 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:Jul 24 - Jul 31

Image gallery for FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

Villa seen from the pool
10 out of 10, Exceptional, (68 reviews)
Exceptional
(68 reviews)

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

Castelnuovo Berardenga

6% off
Price is $1,117
$7,819 for 7 nights
All fees included
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

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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.

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:

  • Boboli Gardens (20.2 mi / 32.5 km)
  • Torrigiani Garden (20.4 mi / 32.8 km)
  • Arno River (20.4 mi / 32.8 km)
  • 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)

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, Tuscany, Italy when booking a vacation rental?
When considering a vacation rental in Castellina In Chianti, Tuscany, an excellent area to stay is the historic center, known for its charming streets and picturesque views of the surrounding vineyards. This neighborhood is home to several delightful attractions, including an impressive medieval castle and beautiful churches that reflect the rich history of the region. Staying in this area allows you to immerse yourself in the local culture while enjoying easy access to nearby wineries, where you can taste some of the finest Chianti wines.

Another great option is the hillside areas surrounding the town, which offer stunning panoramas of the Tuscan landscape. Here, you'll find an abundance of vacation rentals that provide a peaceful retreat, often with the added benefit of outdoor spaces to enjoy the beautiful weather. The proximity to scenic hiking trails and biking paths makes this area ideal for those looking to explore the natural beauty of Tuscany.

Overall, Castellina In Chianti offers a variety of properties, with many options available that cater to different preferences, whether you're seeking a cozy apartment in the heart of the town or a more secluded villa surrounded by olive groves.
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, the most popular vacation rental accommodations are villas, with around 77 available throughout the picturesque Tuscan countryside. These villas often feature multiple bedrooms, expansive living spaces, and fully equipped kitchens, ideal for families and groups looking to enjoy a cozy feel. Many come with outdoor terraces or gardens, allowing guests to soak in the stunning views of the surrounding vineyards and rolling hills.

Additionally, there are about 56 vacation houses and 47 apartments, providing further options for travelers. Vacation houses typically offer a blend of rustic charm and modern amenities, while apartments are often situated in quaint buildings within the village, providing easy access to local restaurants and shops. A few cottages can also be found, adding to the variety of rental choices.
Are there any family house rentals in Castellina In Chianti?
In Castellina In Chianti, Tuscany, there are numerous family-friendly house rentals available—specifically around 119 options to choose from. This picturesque area is known for its stunning landscapes, vineyards, and rich cultural heritage, making it an ideal destination for families seeking both relaxation and adventure. Many of these properties offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.

Visitors can enjoy amenities such as private pools, barbecue areas, and cozy living rooms, great for winding down after a day of sightseeing. The charming village itself is surrounded by beautiful countryside, with opportunities for hiking and cycling, as well as local attractions like wineries and historic sites.
Can I rent a vacation home with a pool or hot tub in Castellina In Chianti?
In Castellina In Chianti, there are plenty of vacation homes available for rent that feature pools or hot tubs, with around 153 options to choose from. This picturesque region in Tuscany is renowned for its stunning landscapes, vineyards, and charming medieval villages. Many of these properties come equipped with private pools, allowing travelers to enjoy refreshing dips while soaking in the surrounding beauty.

In addition to pools, travelers can also find homes with hot tubs, great for unwinding after a day of exploring the beautiful Chianti countryside. Many rentals feature outdoor terraces with scenic views, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a relaxing getaway.
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 wide selection of pet-friendly house rentals, with over 100 options available. Many of these properties are set against the picturesque backdrop of Tuscany's rolling hills and vineyards, providing a tranquil escape for both guests and their furry companions. The rentals typically feature amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups.

The surrounding region offers numerous pet-friendly points of interest, including scenic walking trails through vineyards and olive groves, where pets are welcome to join their owners. Additionally, nearby towns often have pet-friendly cafes and restaurants, allowing travelers to enjoy local cuisine without leaving their pets behind.
Are there any remote work vacation rentals in Castellina In Chianti?
In Castellina In Chianti, Tuscany, there are numerous options for remote work vacation rentals, with around 174 properties available. This picturesque village, set in the heart of the Chianti wine region, offers a serene atmosphere great for focusing on work while enjoying the stunning Tuscan landscape. Many of these rentals come equipped with essential amenities for remote work, including free Wi-Fi and dedicated workspace areas.

Travelers can expect to find traditional Tuscan villas and charming apartments, often featuring beautiful views of rolling vineyards and olive groves. Common amenities include fully equipped kitchens for preparing meals, comfortable living spaces for relaxation, and outdoor areas where one can unwind after a day of work.

Additionally, Castellina In Chianti is conveniently located near local attractions, such as wineries and historic sites, providing a great balance of work and leisure. 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 fully equipped kitchens, superb for travelers who enjoy cooking local Tuscan cuisine. Many rentals also feature cozy fireplaces, adding a warm ambiance during cooler evenings, ideal for a relaxing retreat. Onsite parking is commonly available, making it convenient for those driving through the scenic Chianti region. Additionally, some properties permit pets, allowing travelers to bring their furry companions along, and service animals are welcomed as well.
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 in July, when travelers flock to this picturesque Tuscan village for its stunning landscapes and rich cultural experiences. The peak season, which runs from July to September, brings warm weather, typically ranging from the mid-70s to mid-80s Fahrenheit, superb for exploring the vineyards and enjoying outdoor activities like hiking and cycling.

During these months, visitors can engage in local traditions, savor exquisite Chianti wines, and indulge in the region's renowned cuisine. The vibrant setting is complemented by various festivals and events that celebrate the local culture, making it an ideal time for socializing and enjoying the scenic beauty of the rolling hills.

For those seeking a more budget-friendly option, consider planning your trip in November. While this month sees fewer tourists, it offers a unique charm, with the landscape adorned in autumn colors and the opportunity to experience the region's tranquility. November is also a great time for wine enthusiasts to visit, as it coincides with the grape harvest, allowing for wine tastings and tours at local vineyards without the summer crowds.

Ultimately, the best time to book a vacation rental in Castellina In Chianti will depend on your preferences for vibrant summer activities or a quieter, more intimate experience in the fall.
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, Tuscany, Italy?
In Castellina In Chianti, travelers can immerse themselves in the picturesque landscapes and rich history of Tuscany. The town itself is renowned for its medieval architecture and charming streets, providing a great backdrop for exploration. Visitors can tour the historic Castello di Castellina, which offers insights into the area's past and stunning views of the surrounding vineyards.

The region is also famous for its wine production, and wine lovers can enjoy tastings at local vineyards, many of which are situated just a short drive from the town center. The Chianti Classico Wine Route is a popular attraction, allowing visitors to experience the scenic countryside while sampling some of the best wines in Italy.

Nearby, the beautiful towns of Radda in Chianti and Gaiole in Chianti are also worth a visit, showcasing more of the region's stunning landscapes and culinary delights. Nature enthusiasts can explore the surrounding hills and trails, great for hiking and enjoying the serene environment.
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 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 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.
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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