Castellina in Chianti Holidays from £262

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Castellina in Chianti Holiday

An easy way to experience this city is with a tailor-made Castellina in Chianti holiday package. Base yourself in the neighbourhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. If sightseeing is on the cards during your trip to Castellina in Chianti, look around well-known attractions like Isole e Olena Winery, Il Molino di Grace Winery and Castello di Radda Winery. Check out Expedia's wide range of travel options and begin planning your ultimate holiday to Castellina in Chianti now.

Top Castellina in Chianti Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
Save 100% on your flight
£262
per person
3 Dec - 6 Dec
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
We had a wonderful stay at The Moon hotel. The staff are excellent and we had a speedy and very easy check in experience. The Moon is a beautiful, calm place slightly out of the central sights of Florence, but within an easy walk. Our rooms were beautiful. Great showers and the beds were so comfortable. We slept very well. Breakfast was of a high quality, the fresh egg dishes were delicious. If you like cake for breakfast, you will be spoilt for choice. We used the spa area which was lovely at the end of the day. If not included in your room deal it is extra and you need to book a slot. The hydrotherapy pool is not huge, but works well. Sauna and steam room were very good. Overall a wonderful experience and special thanks to Giorgio for his quick check in and excellent and friendly customer service throughout our stay.

Reviewed on 13 Sept 2026

L'Andana

L'Andana

Save 100% on your flight
£802
per person
17 Oct - 22 Oct
found 17 hours ago
Return flight included
London (LTN) to Florence (FLR)
9.6/10 Exceptional! (94 reviews)
Excellent place

Reviewed on 9 Sept 2026

Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
Save 100% on your flight
£463
per person
26 Oct - 30 Oct
found 6 hours ago
Return flight included
London (LCY) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Clean room, helpful staff, perfect location.

Reviewed on 17 Sept 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
Save 100% on your flight
£450
per person
26 Oct - 30 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Thank you very much for your hospitality

Reviewed on 17 Sept 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence
Save 100% on your flight
£725
per person
20 Oct - 24 Oct
found 18 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (161 reviews)
LOVE this hotel! Perfect location, amazing breakfast, fantastic staff, beautiful rooms, excellent bathrooms. Made our Florence trip amazing highlight of our time in Italy!

Reviewed on 15 Sept 2026

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

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 SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No RainSunnySlightly HighAverage
August75.6°F (24.2°C)No RainSunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
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

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.

Castellina in Chianti Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
1,350
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Siena Cathedral, Tenuta Torciano Winery and Cantina Antinori

Top hotels in Castellina in Chianti

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
£101
21 Sept - 22 Sept
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The indoor pool was undergoing maintenance and the outdoor pool closed at 7, not the 10pm advertised in the hostel’s messages after checking in. The restaurant advertises itself online as being flexible for gluten free/ vegetarian/ vegan. When sitting down and asking, nothing was completely gluten ..."

Reviewed on 16 Sept 2026

Plus Florence - Hostel
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
£149
18 Oct - 19 Oct
includes taxes & fees
The Social Hub Florence Belfiore
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
£139
18 Oct - 19 Oct
includes taxes & fees
9/10 Wonderful! (1,590 reviews)
"Room was standard, but as expected. The bed and pillows were very comfortable, showers were a bit small. Loved the pool and rooftop bar for mid day. On-site Laundry was a bonus! Staff was very friendly!"

Reviewed on 17 Sept 2026

The Social Hub Florence Lavagnini
See all 15,592 properties in Castellina in Chianti
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Stay near popular Castellina in Chianti attractions

Buondonno Winery

9.6/10 (4 reviews)
You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this relaxing area.
See properties

Castellina Fortress

9.4/10 (3 reviews)
Learn about the local history of Castellina in Chianti with a stop at Castellina Fortress. Discover the countryside and wineries in this relaxing area.
See properties

Lilliano Estate Winery

You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
See properties

Casa Vinicola Luigi Cecchi

9.0/10 (4 reviews)
You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area or enjoy its local tours.
See properties

Walls of Monteriggioni

9.2/10 (5 reviews)
You can study the exhibits at Walls of Monteriggioni, a museum with a storied past, during your trip to Castellina in Chianti. Discover the beautiful countryside and wineries in this walkable area.
See properties

Archaeological Museum of Chianti

8.0/10 (6 reviews)
You can browse the exhibits at Archaeological Museum of Chianti, a museum with a story of its own, during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area or enjoy its local tours.
See properties

Mazzei Winery

You can enjoy a tasting or tour at Mazzei Winery during your travels to Fonterutoli. You can enjoy the restaurants while in the area.
See properties

Casina di Cornia Winery

You can enjoy a tasting or tour at Casina di Cornia Winery during your travels to Castellina in Chianti. Discover the countryside and wineries in this relaxing area.
See properties

What to do in Castellina in Chianti

Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

£42
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

£19
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

£61
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
See all activities in Castellina in Chianti

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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.