Castellina in Chianti vacation rentals

We found 2,507 vacation rentals — enter your dates for availability

Discover a selection of 85 homes, 60 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:Sep 12 - Sep 19
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Find out more about Castellina in Chianti

Find out more about Castellina in Chianti

Why visit Castellina in Chianti

  1. Scenic Beauty: Castellina in Chianti boasts breathtaking rolling hills and picturesque landscapes, perfect for outdoor enthusiasts.
  2. Cultural Exploration: The village is rich in history, featuring charming churches, lively piazzas, and historic castles.
  3. Wine Tastings: Indulge in exquisite Chianti wines at local vineyards and wine cellars.
  4. Romantic Atmosphere: Ideal for couples, the enchanting ambiance and cozy Tuscan cottages enhance romantic getaways.
  5. Diverse Accommodations: A variety of vacation rentals, from luxurious villas to charming apartments, cater to all preferences.

Popular types of accommodation in Castellina in Chianti

If you’re looking for the perfect getaway in Castellina in Chianti, you’re in the right place! Our vacation rentals include charming apartments, luxurious villas, and cozy houses. Whether you’re seeking a romantic retreat or a family-friendly escape, you’ll find a variety of accommodations that cater to your needs. Experience the beauty of Chianti with our exceptional villa rentals and vacation homes, designed to provide you with comfort and convenience during your stay.

  • Apartments: The top choice among travelers in Castellina in Chianti, offering a convenient and comfortable stay for couples and families alike.
  • Villas: A popular option for those seeking luxury and ample space, perfect for larger groups or special occasions.
  • Houses: Ideal for visitors wanting a home-like atmosphere, providing privacy and comfort during your stay.
  • Caravan Parks: A unique option for adventurous travelers, combining the charm of nature with essential amenities.
  • Cottages: A cozy retreat, perfect for those looking for a quaint and intimate experience in the heart of Tuscany.**

Top attractions near Castellina in Chianti

Castellina in Chianti offers a romantic and entertaining getaway, perfect for outdoor enthusiasts. Explore charming churches, lively piazzas, and historic castles while indulging in wine tastings. This picturesque Tuscan village is ideal for those seeking culture and romance. Don't miss the enchanting Cambolli Hill and the cozy Tuscan cottages that enhance your experience. Make sure to check off your bucket list with unforgettable activities in this stunning region of Italy.

  1. Monteriggioni Castle: This historic castle, located 6 miles from Castellina in Chianti, offers a glimpse into medieval architecture with its well-preserved walls and towers. Experience the cultural vibes as you stroll through its charming streets and take in the stunning Tuscan landscape.
  2. Siena Cathedral: Situated 11 miles away, this magnificent cathedral features intricate Gothic architecture and stunning artwork. The rich cultural atmosphere invites you to explore its breathtaking interiors and learn about its historical significance.
  3. Piazza del Campo: Also 11 miles from Castellina, this iconic square is known for its unique shell shape. Enjoy the vibrant city vibes, local cafes, and annual events like the Palio horse race, making it a hub of social and cultural activity.

Things to do recommended for couples

Experience romance in Castellina in Chianti by visiting Il Molino di Grace Winery for delightful wine and enchanting vibes. Enjoy a meal at Frateria di Padre Eligio, perfect for couples. Lastly, unwind at Tenuta Maiano, where outdoor charm and entertainment create unforgettable memories together.

Things to do recommended for families

Your family will have a memorable time at the Chianti Observatory, just 4 miles away, enjoying the stars together. For sports enthusiasts, the Stadio Artemio Franchi, located 11 miles away, offers exciting games. Don’t miss the adventure at the Siena Circuit, 15 miles away, perfect for karting fun!

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

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

  • Traveling to Castellina in Chianti with a group: Think about how many bedrooms you require, along with additional features like a full kitchen or outdoor areas for group activities. Thankfully, you can easily filter for these options and much 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 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 Castellina in Chianti: For many families, a vacation wouldn't feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Many of these 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 in search of vacation rentals offering special rates 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 features like a parking space, a well-equipped kitchen, or a private pool in your search!

Where to stay in Castellina in Chianti

Explore the enchanting Castellina in Chianti, where the rolling Chianti hills meet charming villas and an atmosphere of luxury and relaxation. Perfect for romantic getaways or outdoor adventures, this Tuscan gem offers a blend of historical charm and friendly locals. Discover the best vacation ideas as you wander through picturesque landscapes, indulge in fine wines, and unwind in secluded retreats that capture the essence of Tuscany's beauty.

  • Lilliano: Lilliano is a charming village nestled in the heart of Castellina in Chianti, offering travelers a rich cultural experience blended with romance and entertainment. Its scenic landscapes and serene atmosphere make it a perfect getaway for couples and those seeking a peaceful retreat. Notable attractions include a historic building and a local museum, where visitors can immerse themselves in the region's history and art. Additionally, the village serves as a convenient location for attending events at nearby conference venues, enhancing the overall travel experience.
  • Fonterutoli: Fonterutoli is a picturesque village known for its romantic ambiance and outdoor activities, making it a favorite among travelers looking for entertainment and adventure. The area is famous for its stunning vineyards and offers numerous tours that allow visitors to explore the local wine culture. Attractions include historic buildings and monuments that reflect the rich heritage of the region. Fonterutoli's enchanting landscapes and welcoming atmosphere provide an inviting backdrop for leisurely strolls and unforgettable experiences.
  • Ricavo: Ricavo is a quaint village that captivates visitors with its blend of culture, entertainment, and romance. Travelers can embark on guided tours to discover the area's historic places and monuments. The village's unique charm is complemented by its proximity to beautiful beaches, offering a distinct coastal experience amidst the rolling hills of Chianti. Ricavo's inviting ambiance and array of attractions make it a delightful destination for anyone looking to experience the best 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnyAverageAverage
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 LowSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Moreover, opting for a longer stay frequently results in better savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! When you join our travel rewards program, OneKey, you'll gain access to exclusive member savings and can earn and redeem OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your travels. You can easily create new trips, resume planning your existing itineraries, or view and organize all your travel arrangements in one place. Your saved or booked properties will be neatly organized into categories like Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/en-ca/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:

  • 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)
  • Chianti Sculpture Park (7.2 mi / 11.6 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?
Lilliano is one of the more popular neighborhoods to find a vacation home in Castellina in Chianti. Choose from our collection of relaxing stays and then get out and experience this destination like a local.
What is the most popular type of vacation rental accommodation in Castellina in Chianti?
According to our data, apartments are considered the most popular type of property in Castellina in Chianti. But of course, everyone’s idea of an epic trip differs. Vrbo has vacation rentals in a variety of shapes and sizes, and we’ll help you locate the perfect fit.
How much does it cost to rent a vacation rental in Castellina in Chianti?
The average price for a vacation rental in Castellina in Chianti depends on a number of factors, such as property type, length of stay and time of year. Whether you’re thinking about a sprawling villa with space for the whole family or a cozy condo just for the two of you, just enter your dates of travel to see stays with exceptional value.
How much does it cost to rent a beach house in Castellina in Chianti?
Prices for beach houses in Castellina in Chianti can differ depending on the size and style of the property and when you’re traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to narrow your search results by ratings, amenities and more.
Are there pet-friendly vacation rentals in Castellina in Chianti?
With 236 properties that welcome pets, your furry best friend can join you on your Castellina in Chianti getaway. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect vacation home on Vrbo.
Can I rent a house with a pool in Castellina in Chianti?
Mark the “pool” box in our filter tool and you’ll find 198 houses with private pools in Castellina in Chianti on Vrbo. Lazy soak or ball games and races? Leisure time is your call when your vacation home has its own pool.
What are popular rental amenities in Castellina in Chianti?
Some of the most popular rental amenities people are searching for in Castellina in Chianti are a barbecue grill, a firepit and a chef. Whether you’re traveling with family, buddies or even pets, Vrbo vacation rentals feature the best amenities for beginning new traditions with the people closest to you.
Are there large group vacation rentals in Castellina in Chianti?
Castellina in Chianti has 35 vacation homes that can cater to 10 or more guests. These stays come with the space you need to share good times with your favorite people.
Are there vacation rentals in Castellina in Chianti that welcome kids?
With 211 family-friendly vacation properties to pick from in Castellina in Chianti, now is an awesome time to introduce your children to the pleasures of travel. Click on our “Properties good for families” filter to search for stays that feature conveniences perfect for vacationing families, like living rooms, backyards, entertainment areas and hot tubs.
What are the top attractions for families in Castellina in Chianti?
Keeping the kids happy during your Castellina in Chianti vacation is easy with these exciting family-friendly attractions:

  • Walls of Monteriggioni
  • Castellina Fortress
  • Archaeological Museum of Chianti

Are there one-bedroom vacation rentals in Castellina in Chianti?
Yes, Castellina in Chianti has 38 one-bedroom rentals available. Often located in sought-after areas thanks to their compact size, a one-bedroom vacation rental is great if you’re getting away with a pal or your partner. And with comforts like air conditioning and more privacy than a standard hotel, you’ll be able to chill out while exploring this exciting destination.
Can I find two-bedroom vacation rentals in Castellina in Chianti?
Take off with your besties and enjoy peace, privacy and comfort in one of the 98 two-bedroom vacation properties Castellina in Chianti has to offer.
Are there vacation rentals with WiFi in Castellina in Chianti?
Whether you’d like to keep up to date with the news, look over emails or update your social media accounts, there are 81 vacation homes with WiFi in Castellina in Chianti. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Castellina in Chianti?
Work out your travel dates and then use the filters to search for vacation rentals with ac in Castellina in Chianti on Vrbo. With 74 air-conditioned properties to choose from here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a vacation rental in Castellina in Chianti?
It’s advisable to check with the Castellina in Chianti vacation property you’d like on Vrbo as age restrictions differ. However, generally it’s 16, 18 or 21.
How long can I rent a vacation rental in Castellina in Chianti for?
It’s up to the Castellina in Chianti property. To view all available options offering extended stays, simply type your travel dates and number of people into the Vrbo search page. Look forward to having the property to yourself, as well as comforts such as a fully-equipped kitchen and a backyard where the little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Castellina in Chianti?
On Vrbo, we’ve got some amazing discounts and bargains for Castellina in Chianti. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a weekend retreat or an extended stay, Vrbo has lots of options for all budgets and styles.

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