A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Holidays from £290

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Top Castellina in Chianti flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 27 Sept - 29 Sept

    Aurum Firenze + Flight

    Historic Centre of Florence
    2 nights
    4.0 star property
    7.4/10 - Good (1,008 reviews)
    Return London (LGW) - Florence (FLR)
    LGW - FLRDirect FLR - LGWDirect
    Save 100% on your flight
    £502
    £290
    per traveller
    found 1 day ago
    Aurum Firenze
  • 11 Oct - 16 Oct

    The Moon Boutique Hotel & Spa + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.6/10 - Exceptional (580 reviews)
    "Everything was great! Friendly staff, clean and comfortable rooms, and a relaxing atmosphere overall. We really enjoyed our stay!"
    Reviewed August 1, 2026
    Return Birmingham (BHX) - Florence (FLR)
    BHX - FLR1 stop FLR - BHX1 stop
    Save 100% on your flight
    £1,569
    £841
    per traveller
    found 15 hours ago
    The Moon Boutique Hotel & Spa
  • 6 Sept - 10 Sept

    Aurum Uffizi + Flight

    Historic Centre of Florence
    4 nights
    4.0 star property
    7.6/10 - Good (1,003 reviews)
    "The room was clean and air conditioning worked well for the size of room. However, the room was a little small for a family of four. The location was one of the best aspects of the hotel: it was right in the historic centre and near all the attractions. Staff were also very helpful, promptly responding to our requests."
    Reviewed August 2, 2026
    Return London (LON) - Florence (FLR)
    LGW - FLRDirect FLR - LGWDirect
    Save 100% on your flight
    £777
    £417
    per traveller
    found 21 hours ago
    Aurum Uffizi
  • 13 Sept - 17 Sept

    Precise Tale Poggio Alla Sala + Flight

    Montepulciano
    4 nights
    5.0 star property
    9.6/10 - Exceptional (156 reviews)
    "The place it’s an Amazing. Very clean. Is more beautiful than the pictures."
    Reviewed August 2, 2026
    Return London (LON) - Florence (FLR)
    LTN - FCODirect FCO - LTNDirect
    £2,674
    £1,477
    per traveller
    found 1 day ago
    Precise Tale Poggio Alla Sala
  • 11 Oct - 16 Oct

    Alfieri9 + Flight

    Historic Centre of Florence
    5 nights
    3.0 star property
    9.6/10 - Exceptional (170 reviews)
    "More quiet residential area of Firenze in walking distance of center but away from the crowds. No elevator and two flight of stairs."
    Reviewed July 5, 2026
    Return Birmingham (BHX) - Florence (FLR)
    BHX - FLR1 stop FLR - BHX1 stop
    Save 100% on your flight
    £1,085
    £629
    per traveller
    found 15 hours ago
    Alfieri9

Discover the most popular places to visit in Castellina in Chianti

What to do in Castellina in Chianti

Castellina in Chianti Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

Why should I book my Castellina in Chianti holiday with Expedia?

With exceptional-value airfares, hotel and car hire choices all in the same place, Expedia makes booking your Castellina in Chianti adventure hassle-free. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Select from wonderful retreats, add your flights and/or a car hire (and maybe even some exciting tours and activities!) and score unbeatable prices. Need to change plans? Expedia has a flexible cancellation policy for many reservations. To find out more, head over to our Customer Service Portal link.

When is the best time of year to holiday in Castellina in Chianti?

Into sightseeing but don't like big crowds? Plan your Castellina in Chianti escape for November, December and January. Typically, it's much quieter than it is in March, May and August. Organise your escape to Castellina in Chianti based on what type of adventure you want. January is the coolest time of year, when daytime temperatures average 4ºC. In July, the warmest period, you'll experience temperatures of around 24ºC during the day.

What are the top hotels for my holiday in Castellina in Chianti?

Many people like to stay at Castello di Fonterutoli Wine Resort in San Leonino. If it's your first visit to Castellina in Chianti, you'll feel right at home here.

How do I get a cheap holiday to Castellina in Chianti?

Our Castellina in Chianti holidays promise plenty of savings for the savvy globetrotter. For the best deals, simply bundle your flights, hotels and extras (such as activities). But bargain prices are only the start of your next epic adventure. When you book with Expedia, and you'll have over 400 airlines and 321,000 properties all over the world to select from. No matter your style or budget, there's a holiday here with your name on it. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.

What should I do on my Castellina in Chianti holiday?

Offering must-visit attractions such as Monteriggioni Castle and Meleto Castle, a holiday in Castellina in Chianti is filled with exciting places to visit. Castello di Radda Winery and Castello di Albola are a couple of other sights also worth exploring.

What is the best area to stay in when on holiday in Castellina in Chianti?

If you plan to visit Buondonno Winery, save yourself the hassle of commuting and book a stay close by. It's one of the most popular attractions in Castellina in Chianti.

Do I need a visa for my Castellina in Chianti holiday?

Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for work or holidays, will determine if you'll need a visa for Castellina in Chianti. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your date of return. Do all your travel planning well ahead of time to avoid any last-minute surprises.

What should I wear on my Castellina in Chianti holiday?

Do a little research into the sorts of things people in Castellina in Chianti wear, and consider browsing style blogs for some fashion inspiration. Try to create a versatile wardrobe filled with pieces that work for your destination and show off your unique sense of style. Daytime temperatures in January, Castellina in Chianti's coolest month, average 4ºC. July marks this city's warmest month when the average temperature reaches 24ºC. Our top tip? Take the guesswork out of packing and check the local weather conditions.

What does an Expedia Castellina in Chianti holiday include?

Expedia has all you need to lock in your Castellina in Chianti trip, but what your package looks like is entirely up to you. Pick from a combination of hotels, flights and hire cars. In search of some tours or activities to keep you on the move? Once you've made your booking, you can add them too. Whatever your budget or style, there's a package to meet your needs. Explore a large selection of property types and pick one that suits the size of your group. The most popular holiday rentals here are apartments and villas. With Expedia, you can easily tailor your Castellina in Chianti escape any way you want.

Does Expedia offer Book Now, Pay Later Castellina in Chianti holidays?

Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions is what works best for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • No-deposit holidays: When you want to jump on an unbeatable deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Castellina in Chianti Expedia holiday?

Yes, and with over 400 airlines to pick from all over the world, you're not short on choice. Take a look at the available options and find out which airline suits your needs and budget.

Book with confidence

Things to do near Castellina in Chianti

Castellina in Chianti offers a delightful blend of romance and outdoor activities, making it an ideal getaway. Visitors can indulge in spa treatments and explore the local theatre scene. For the adventurous, hiking tours and cycling through the picturesque Chianti region provide a unique way to experience the stunning landscapes and charming villages. Whether you seek relaxation or excitement, Castellina in Chianti has something to enchant every traveller.

Shopping

In Castellina in Chianti, you can visit local shops for unique souvenirs. If you're up for a drive, The Mall Luxury Outlet is 29.0km away, offering luxury brands. Pitti Vintage, located 32.2km away, features vintage finds, while the Central Market, 33.8km away, boasts local produce and crafts.

Recreation

Experience serenity at Alta Val d'Elsa River Park, where nature promotes relaxation just 16.1km from Castellina in Chianti. For sports enthusiasts, Stadio Artemio Franchi offers thrilling events 17.7km away. Indulge in luxury at Villa a Sesta Polo Club, a prestigious private club located 24.1km from your base.

Adventure

Embark on a scenic hike with Hedonistic Hiking, located 17.7km from Castellina in Chianti, where stunning landscapes await. Experience thrills at the Siena Circuit karting venue, 24.1km away, perfect for adrenaline seekers. For a unique outdoor experience, visit Biolago Geotermico Acqua Harda, situated 48.3km from the town.

Nightlife

Experience the vibrant nightlife of Castellina in Chianti by visiting Il Fiaschetto, a charming drinking pub located 25.7km away. Enjoy a laid-back atmosphere filled with entertainment and romantic vibes, perfect for a memorable evening out in the heart of Tuscany.

Find the best attractions in and around Castellina in Chianti

Castellina in Chianti, a charming destination in Tuscany, is ideal for romantic and outdoor getaways. Visitors can explore historic churches, picturesque piazzas, and enchanting castles, all while enjoying the rich culture and stunning scenery. Wine enthusiasts can indulge in local Chianti wineries, while those seeking relaxation can consider the best villas in Castellina. This delightful Italian town offers a perfect blend of romance and entertainment for all types of travellers.

  • Piazza del Campo: Located 17.7km from Castellina in Chianti, this iconic square is renowned for its stunning medieval architecture and vibrant atmosphere. It hosts the famous Palio horse race and offers a taste of Sienese culture with numerous cafes and shops surrounding it.
  • Meleto Castle: Just 11.3km away, this enchanting castle boasts romantic vibes and rich history. Visitors can explore its beautiful gardens, ancient walls, and enjoy breathtaking views of the Tuscan countryside, making it a perfect spot for a picturesque day out.
  • Archaeological Museum of Chianti: Situated within Castellina in Chianti, this museum offers a fascinating glimpse into the region's ancient past. With various artefacts and exhibits, it showcases the cultural heritage of Chianti, making it a must-visit for history enthusiasts.

Best time to go to Castellina in Chianti

The best time to visit Castellina in Chianti is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Tips to save on your trip to Castellina in Chianti

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Castellina in Chianti.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.