Castellina in Chianti holiday rentals

We found 2,292 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

  • Historical Charm: Stroll through ancient streets and piazzas, where centuries-old churches and a storied castle reflect Castellina’s rich heritage.
  • Romantic Ambience: Enjoy the serene, picturesque landscapes that make this Tuscan village a perfect setting for a romantic retreat.
  • Cultural Exploration: Discover the local history by visiting traditional landmarks and quaint neighbourhoods filled with authentic Italian charm.
  • Scenic Outdoors: Embrace the outdoor allure with gentle walks amidst rolling hills and classic Chianti vistas.
  • Gastronomic Delights: Savour local cuisine and traditional flavours that complete the authentic Italian experience within Castellina.

Popular types of accommodation in Castellina in Chianti

Discover the charm of Castellina in Chianti – a Tuscan gem offering stylish accommodations, including apartments, villas, and private holiday homes. Enjoy the rich history, exquisite local cuisine, and stunning landscapes while exploring ancient landmarks and quaint streets. Your perfect stay in Castellina awaits, ensuring a memorable and authentic Italian holiday experience.

  • Apartments: A popular choice for visitors, these self-contained units offer the comforts of home with the flexibility to explore local cuisine.
  • Villas: Often set in picturesque surroundings, villas provide spacious and luxurious accommodations for families or groups seeking a relaxing getaway.
  • Private Holiday Homes: Ideal for those wanting a personal touch, these homes offer privacy and the chance to experience local life.
  • Caravan Parks: A unique option for adventurous travellers, caravan parks offer a blend of comfort and nature, perfect for a laid-back holiday.
  • Cottages: These quaint and charming abodes are perfect for a cosy retreat, providing a warm atmosphere and rustic charm.**

Top attractions near Castellina in Chianti

Castellina in Chianti in Tuscany offers a charming blend of culture and romance. Wander through the historic piazza, visit ancient churches and explore the castle that stands as a testament to its storied past. Ideal for those seeking an outdoor holiday and entertainment, this locale enchants visitors with its rich heritage and captivating experiences, all set amidst the scenic Tuscan landscape.

  • Piazza del Campo: A stunning square renowned for its unique shell shape, vibrant atmosphere, and historic significance. It hosts the famous Palio horse race, showcasing a blend of culture and local tradition.
  • Fortezza Medicea: This historic fortress offers a glimpse into the past with its impressive architecture and panoramic views. It serves as a cultural hub, often hosting events and exhibitions.
  • Siena Cathedral: A masterpiece of Gothic architecture, this cathedral is adorned with intricate details and stunning artworks, providing a remarkable insight into the region's rich history and artistry.

Things to do recommended for couples

For a romantic getaway in Castellina in Chianti, indulge in wine tastings at local vineyards, enjoy candlelit dinners with exquisite Tuscan cuisine, and take leisurely strolls through the picturesque vineyards. Don’t miss a sunset hot air balloon ride for breathtaking views of the Chianti landscape.

Things to do recommended for families

Families exploring Castellina in Chianti can enjoy a delightful day at the local vineyards, where kids can learn about grape harvesting. Additionally, a visit to the picturesque Chianti Sculpture Park offers fun outdoor art installations, perfect for a family stroll and creative photo opportunities.

Things to do recommended for groups

Embark on an exhilarating day at Saltalbero Adventure Park, a zipline ropes course located 32km away from Castellina in Chianti, where adventure and the great outdoors await your group.

*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, ensure you select the appropriate filters. Here are some Stayz booking pointers for you.

  • Traveling to Castellina in Chianti with a group: Consider how many bedrooms you'll require, along with facilities such as a fully-equipped kitchen or outdoor space for a group gathering. Fortunately, you can filter for all these features, and more, on Stayz.
  • Traveling to Castellina in Chianti with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to Castellina in Chianti: For some, a family holiday is incomplete without the company of their four-legged companion. If this resonates with you, explore Stayz accommodations that welcome pets. Many pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels truly at home.
  • Planning for a long term stay visiting Castellina in Chianti: If you’re searching for holiday lets offering discounts for stays of a month or more, you’ve come to the right spot. With the appropriate filters, you can effortlessly locate and secure savings on monthly rentals. Be sure to include options such as parking, a well-equipped kitchen or a private pool in your search.

Where to stay in and around Castellina in Chianti

Castellina in Chianti offers an enchanting retreat, perfect for a romantic and luxury getaway. Explore its historical streets, secluded corners and vibrant village life where charming hotels await. Enjoy the serene atmosphere of its classic Chianti village, ideal for a relaxing holiday experience, complete with quaint seating areas and picturesque landscapes that capture the essence of Tuscany.

  • Sicelle: Nestled within the heart of Castellina in Chianti, Sicelle is a charming village that invites travellers seeking a romantic, entertainment-themed, and outdoor experience. The picturesque setting is ideal for those who relish leisurely strolls and engaging recreational activities, with ample opportunities for sports and swimming in the neighbouring areas. Its serene atmosphere and traditional Tuscan character make Sicelle a delightful retreat for exploring the region’s cultural heritage and natural beauty.
  • Colle Petroso: Situated a mere 3km from Castellina in Chianti, Colle Petroso offers visitors a blend of romantic charm and a dynamic entertainment-themed ambience. This quaint village is renowned for its proximity to historical landmarks such as an ancient castle, a venerable church, and notable historic buildings. The scenic surroundings provide an inviting mix of outdoor pursuits and cultural excursions, making it an appealing destination for those eager to immerse themselves in Tuscany’s storied past and vibrant present.
  • Lilliano: Located within the Castellina in Chianti area, Lilliano is a village that perfectly marries outdoor adventure with romantic allure and a dash of entertainment. It boasts attractions such as a visitor centre, a sports museum, and a castle, all of which offer a window into the local heritage and active lifestyle. Whether you are passionate about exploring historical sites or indulging in leisurely outdoor activities, Lilliano provides a well-rounded experience that captures the essence of Tuscan living.

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 Stayz is a breeze

Are you hoping to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, you might find considerable savings by opting for a longer stay. To discover a Stayz property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's innovative Trip Board offers you a dedicated space to plan new trips, resume your previous arrangements, or manage your itinerary. You can easily access the properties you've saved or booked, now conveniently organised under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.stayz.com.au/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? Stayz 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 Stayz 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 Stayz.
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 Stayz, 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, Stayz 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 Stayz 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 Stayz 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 Stayz, 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 Stayz 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.