Castellina in Chianti holiday homes

We found 2,294 holiday rentals — enter your dates for availability
Discover a selection of 27 homes, 16 apartments and other holiday rentals in Castellina in Chianti that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Castellina in Chianti

Showing deals for:30 Oct - 6 Nov

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Why visit Castellina in Chianti

  • Rich Cultural Heritage: Explore historic churches and charming piazzas that reflect the town's deep-rooted traditions.
  • Majestic Castle: Visit the impressive castle that offers stunning views and a glimpse into Castellina's history.
  • Cycling Tours: Enjoy scenic cycling routes through the picturesque Chianti countryside, perfect for adventure enthusiasts.
  • Rustic Wine Estates: Discover local wine estates and savour the authentic flavours of the Chianti region.
  • Serene Outdoor Experiences: Unwind in tranquil outdoor settings, ideal for relaxation and immersing in Tuscany's beauty.

Top attractions near Castellina in Chianti

Castellina in Chianti offers a romantic and entertaining escape with its rich cultural heritage. Visitors can explore historic churches, charming piazzas, and a majestic castle, all nestled within the city. Ideal for those seeking a blend of culture and adventure, travellers can enjoy cycling tours and scenic villa experiences while immersing themselves in the timeless allure of Tuscany.

  • Piazza del Campo: Experience the vibrant city and cultural ambience of this piazzaSquare, just 18km from Castellina in Chianti, where historic charm meets lively local traditions.
  • San Gimignano Communal Palace: At 19km away, immerse yourself in the rich heritage and cultural vibes of this historic civic government building, echoing tales of Tuscany's past.
  • Porta Camollia: Explore this historic gate arch located 16km from Castellina in Chianti, offering a glimpse into the region's storied cultural legacy.

Things to do recommended for couples

For a romantic getaway in Castellina in Chianti, indulge in a wine tasting tour at a local vineyard, enjoy a scenic picnic amidst the stunning landscapes, or take a leisurely stroll through the charming streets. Don't forget to savour a candlelit dinner featuring traditional Tuscan cuisine.

Things to do recommended for families

In Castellina in Chianti, families can explore enchanting vineyards, enjoy bike rides through scenic hills, and visit local farms for hands-on cheese-making experiences. Don't miss the chance to taste delicious gelato while wandering the charming streets, creating unforgettable memories together.

Things to do recommended for groups

Experience the thrill of the Saltalbero Adventure Park, a rope course and zipline located 32km from Castellina in Chianti. Enjoy the outdoor adventure vibes with your group as you tackle the challenges and create lasting memories together in the stunning Tuscan countryside.

*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

Whether you’re journeying with a group, travelling as a family, bringing your pets along, or seeking extended stays, be sure to filter by the appropriate priorities. Here are some Vrbo booking tips for you.

  • Traveling to Castellina in Chianti with a group: Consider how many bedrooms you'll require, as well as amenities like a fully-equipped kitchen or an outdoor area for group get-togethers. Thankfully, you can easily apply filters for all these features, and more, on Vrbo.
  • Traveling to Castellina in Chianti with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to take into account how close you are to family-friendly attractions.
  • Taking your pets with you to Castellina in Chianti: Some travellers believe a family holiday isn’t complete without their furry mate tagging along. If that sounds like you, then have a look at Vrbo properties that welcome pets. Many pet-friendly properties come with feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Castellina in Chianti: If you’re after holiday rentals offering discounts for month-long stays, you've come to the right spot. With the right filters, you can effortlessly discover and save on monthly rentals. You might also want to include options like a parking spot, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Castellina in Chianti

Discover the charm of Castellina in Chianti, where the enchanting Chianti countryside unfolds with rustic wine estates and romantic hidden gems. Enjoy a relaxing Tuscan holiday amidst historical streets, luxury escapes, and serene outdoor experiences, perfect for unwinding in a secluded setting. Experience local culture, savour the flavours of the region, and immerse yourself in the timeless beauty of Tuscany.

  • Sicelle: Nestled in the heart of the Chianti region, Sicelle is a quaint village that offers an idyllic mix of romance, entertainment, and outdoor adventures. Wander through its scenic landscapes and enjoy local sports and swimming activities that reflect the relaxed Italian lifestyle. With its proximity to Castellina in Chianti, Sicelle provides travellers with a serene retreat where culture and nature blend seamlessly.
  • Lilliano: A charming village in the Castellina in Chianti area, Lilliano invites visitors to indulge in its outdoor, romantic, and entertainment-themed experiences. The village is surrounded by notable landmarks including a visitor centre, a sports museum, and an impressive castle. Its picturesque setting is perfect for leisurely strolls and immersive cultural experiences, making it a delightful spot to explore.
  • Radda in Chianti: Just 6km from Castellina in Chianti, Radda in Chianti is a historic city that captivates travellers with its blend of romance, entertainment, and outdoor activities. Known for its elegant spa and body treatment facilities, as well as a golf course, the city also boasts significant historical landmarks such as a castle, a historic site, and a monument. Radda in Chianti offers a well-rounded travel experience that caters to both relaxation and cultural exploration.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.8°F (4.9°C)Light RainMostly SunnyAverage
February42.8°F (6.0°C)Light RainMostly SunnyAverage
March47.5°F (8.6°C)Light RainMostly SunnyAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly High
May60.4°F (15.8°C)Light RainMostly SunnyAverage
June69.8°F (21.0°C)Light RainSunnyAverage
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnySlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly Low
November50.0°F (10.0°C)Light RainMostly SunnySlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Looking to cut costs on your next adventure? Consider being flexible with your travel dates, as prices can vary. By opting for a longer stay, you can often reap considerable savings. To find the perfect Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform to create new trips, resume your planning, or manage your existing travel arrangements. You’ll easily find your saved or booked properties organised into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.bookabach.co.nz/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 attracts visitors thanks to its forests and bird watching. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Castellina in Chianti

Do you want to discover things to do while you're in the area? Venture out of your holiday home and check out everything that makes Castellina in Chianti a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 traveller or just want to appreciate the scenery, Castellina in Chianti is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Chianti Sculpture Park (7.3 mi / 11.7 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)
  • Val di Merse (20.6 mi / 33.2 km)
  • Sentierelsa Trail (8.4 mi / 13.6 km)

Travelling to and around Castellina in Chianti

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

Frequently asked questions

What is the best area to stay in Castellina in Chianti when booking a holiday home?
If you're considering a Castellina in Chianti getaway, Lilliano is one of the most desirable places to stay. Whether you go for a condo, cottage or another property style, you'll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Castellina in Chianti?
The most popular types of holiday homes in Castellina in Chianti are apartments. Ready for more choices? Bookabach has numerous options to match our guests' unique needs, so you'll see holiday properties in loads of shapes and sizes. The ideal home away from home is waiting for you — get hold of yours today.
How much does it cost to rent a holiday home in Castellina in Chianti?
The average price for a holiday home in Castellina in Chianti depends on several factors, like length of stay, property type and season. Whether you're searching for a sprawling villa with space for extended family or a quaint cabin ideal for just you and the kids, just add your travel dates to find stays with amazing value.
How much does it cost to rent a beach house in Castellina in Chianti?
The average price for a holiday home near the beach in Castellina in Chianti depends on when you're visiting the area and the style and size of property you're looking for. You can quickly and easily find prices on Bookabach by entering your dates of travel. Then use the filters to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Castellina in Chianti?
Yes. You'll have your pick of 217 holiday homes that cater to pets in Castellina in Chianti. Many of our pet-friendly holiday homes have an outdoor space for your furry friend to play in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect place on Bookabach.
Can I rent a house with a pool in Castellina in Chianti?
Add an extra element of fun to your adventure by staying in one of the 187 houses with a private pool in Castellina in Chianti. Use our search filter to find the kind of property you want on Bookabach, and then spend carefree days splashing and playing in a swimming pool that's for your use only.
What are popular home amenities in Castellina in Chianti?
The most popular home amenities people are searching for in Castellina in Chianti are nearby museums, an electric car charging station and a chef. Whether you're on the road with family, friends or even pets, Bookabach holiday properties come with the best amenities for beginning new traditions with the people who matter most.
Are there large group holiday homes in Castellina in Chianti?
There are 29 holiday homes in Castellina in Chianti that can host a group of 10 or more guests. Whether you're organising a trip with the family or an event like a party, there's enough room to get your favourite people together under the same roof.
Are there holiday homes in Castellina in Chianti that welcome kids?
Bring the entire group together for a fun-filled adventure in Castellina in Chianti at one of our 217 family-friendly holiday homes. Lots of these stays offer amenities that are suitable for trips with the little ones, such as dining rooms, living rooms and entertainment units. Simply click on the "Properties good for families" filter and book your favourite.
What are the top attractions for families in Castellina in Chianti?
Keeping the kids entertained during your stay in Castellina in Chianti is a snap with these cool family-friendly attractions:

  • Monteriggioni Castle
  • Meleto Castle
  • Castello di Radda Winery

Are there one-bedroom holiday homes in Castellina in Chianti?
Castellina in Chianti has 41 one-bedroom homes on offer. Often positioned in desirable areas due to their compact size, a one-bedroom holiday home is ideal if you're travelling with your partner or a buddy. And with home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back and relax while discovering this exciting destination.
Can I find two-bedroom holiday homes in Castellina in Chianti?
Pick from 95 two-bedroom holiday properties in Castellina in Chianti. Give your little ones the second room or fill it with a couple of your best buddies. There's a spot for whoever's fortunate enough to come along for the ride.
Are there holiday homes with WiFi in Castellina in Chianti?
Whether you'd like to keep up with the headlines, send some emails or surf social media, there are 68 holiday homes with WiFi in Castellina in Chianti. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Castellina in Chianti?
Castellina in Chianti has 63 holiday homes where you'll be able to kick back in air-conditioned comfort. To find a property on Bookabach offering this perk, enter your preferred travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Castellina in Chianti?
The minimum age can differ across properties on Bookabach, so be sure to look at the rules of the holiday home in Castellina in Chianti you're considering. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Castellina in Chianti for?
It's up to the Castellina in Chianti property. To look over a list of options offering extended stays, simply type your travel dates and guest number into the Bookabach search page. Enjoy having the entire place to yourself, along with home comforts such as a fully-equipped kitchen and outdoor spaces to play in. Keep your eyes open for long-term stays that offer weekly or monthly discounts.