Chianti Region Holidays from £343

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Your Chianti Region Holiday

Make putting together your next amazing adventure a breeze with a holiday package to Chianti Region. If it's walking trails, cycling and views you want to experience, Montevarchi is waiting for you. Begin your trip to Chianti Region with a couple of days in San Gimignano visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Radda in Chianti is another city that draws crowds from near and far. Castello di Albola and Meleto Castle are two of the top places to see in this destination. Expedia has everything you need when it comes to planning your Chianti Region holiday. From hotels and flights, to car rentals and more, we know how to create a travel experience like no other.

The Latest Chianti Region Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Castello di Pontebosio Luxury Resort

Castello di Pontebosio Luxury Resort

4 out of 5
Save 100% on your flight
per person
16 Jun - 20 Jun
found 10 hours ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.4/10 Exceptional! (51 reviews)
We absolutely loved our stay at the Castle. The staff was fabulous, The young lady in the office was extremely helpful and made dinner reservations for us at one of the best dining experiencing we ever have at restaurante La Torre.

Reviewed on 14 Apr 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
per person
5 Jul - 11 Jul
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.4/10 Exceptional! (110 reviews)
Property is beautiful but rooms used to be stable and are too small, old, and without amenities and inconvenient. Oh and there's no air conditioner

Reviewed on 31 Mar 2025

Residenza Florentia

Residenza Florentia

1 out of 5
Duomo
Save 100% on your flight
per person
7 Jun - 12 Jun
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
8.6/10 Excellent! (35 reviews)
It was right in the heart of Venice, and walkable from the boat port from the airport. However, if you have lots of luggage, there are several bridges to cross and the cobblestone street made it difficult to maneuver my luggage. When we left, we took a private boat from the rear of the hotel, which made it very convenient to the train station. The historical beautiful property was very special.

Reviewed on 27 Nov 2024

Aurum Uffizi

Aurum Uffizi

4 out of 5
Santa Croce
Save 100% on your flight
per person
25 Jun - 29 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.8/10 Good! (1,006 reviews)
Nice and clean room, good sheets and towels. Staff very nice, they allow to leave your luggage after checkout and come pick it up later.

Reviewed on 29 Apr 2025

Boccioleto Resort&Spa

Boccioleto Resort&Spa

4 out of 5
Save 100% on your flight
per person
5 Jul - 11 Jul
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (84 reviews)
Great place!! Unfortunately we got there the day the day after they had open. If there a day after they opened for the season and there are a few things we needed that were not sorted.

Reviewed on 18 Mar 2025

Chianti Region Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)

Our pick of the best Chianti Region Hotel Deals

Hotel Borgo di Cortefreda Relais
Hotel Borgo di Cortefreda Relais
4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Stay at this 4-star spa hotel in Barberino Tavarnelle. Enjoy free breakfast, free parking and an outdoor pool. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (408 reviews)
"Wonderful hotel with a great view, great staff, and the food was fantastic!"

Reviewed on 29 Apr 2025

Hotel Borgo di Cortefreda Relais
Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Spaltenna- Small Luxury Hotels of the World
5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Stay at this 5-star spa hotel in Gaiole in Chianti. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Church of San Sigismondo and Gaiole ...
9.4/10 Exceptional! (220 reviews)
"Staff, spa and food was all perfect"

Reviewed on 1 Oct 2024

Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Ristorante Alcide
Hotel Ristorante Alcide
4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Stay at this 4-star business-friendly hotel in Poggibonsi. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff in their ...
8/10 Very Good! (443 reviews)
"Very good property"

Reviewed on 26 Sep 2024

Hotel Ristorante Alcide
See all 5,060 properties in Chianti Region
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

Frequently asked questions

Why should I book my Chianti Region holiday with Expedia?
Expedia has your back for every detail of your next Chianti Region trip. You’ll always land the best deal possible, but when you bundle your flights, hotel and/or car hire into a holiday package, you’ll save even more. Want to truly make the most of your break? Add a few exciting tours and activities to your package. Expedia offers flexible cancellation policies on almost all bookings, so there’s no need to stress if your travel plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Chianti Region?
If you enjoy the atmosphere of peak season, head to Chianti Region in May, June and August. If you prefer a calmer vibe, November, December and January are better times to visit. Arrange your escape to Chianti Region based on what style of adventure you’re looking for. January is the coolest time of year, when average daytime temperatures are 4ºC. In July, the warmest month, you’ll experience temperatures of around 24ºC during the day.
What are the top hotels for my holiday in Chianti Region?
For properties in Val dElsa with cosy beds and friendly service, check out Grand Hotel Duomo and NH Pisa. If you plan to explore Greve in Chianti as well, you’ll get a great night’s sleep at Hotel Spadai or Grand Hotel Baglioni.
How do I get a cheap holiday to Chianti Region?
Booking a flight and hotel together with Expedia won’t just save you time — it’ll save you money too. A Chianti Region holiday makes it simple to create the ideal trip. With more than 400 airlines across the world to select from, finding convenient flights that suit your schedule will be no sweat. Not only that, we have over 321,000 hotels globally to choose from. Now that’s what you call choice. Whatever your budget, Expedia puts the world within your reach. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chianti Region holiday?
Plan your next holiday in Chianti Region around major attractions like Collegiate Church of Santa Maria Assunta and The Mall Luxury Outlet. Many sightseers also recommend Antinori nel Chianti Classico and Tenuta Torciano Winery.
What is the best city to stay in when on holiday in Chianti Region?
Val dElsa is a great base for your holiday. Find a cosy stay here and start exploring this city’s best attractions, like Collegiate Church of Santa Maria Assunta.
Do I need a visa for my Chianti Region holiday?
Check the latest information on official government websites. Your nationality and whether you’re visiting for work or pleasure will determine if you require a visa for Chianti Region. Get familiar with the application process, including the required documentation, turnaround times and fees. Finalise your application well in advance to allow enough time for processing. Some visas may take weeks or even months to go through, depending on the country.
What should I wear on my Chianti Region holiday?
First, think about the type of activities planned during your trip to Chianti Region and select versatile pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, browse a few style blogs or social media accounts. It’s also a smart move to check the weather forecast so you can pack appropriately. July is the warmest month in Chianti Region, with average temperatures of 24ºC. January is when much of this destination is at its coolest, so pack your cases for daily temperatures of around 4ºC.
What does an Expedia Chianti Region holiday include?
With Expedia, you can select any combination of car hires, hotels and flights to create your ideal Chianti Region travel package. Once you’ve made your booking, simply add on the fun stuff like day tours and activities. Remember — the more you bundle, the more you’ll save! Expedia offers a wide array of properties in Chianti Region, giving you the flexibility to tailor-make your holiday. Apartments and villas are two of the most-favoured options for our customers here.
Does Expedia offer Book Now, Pay Later Chianti Region holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that suits best during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that suit all budgets, so you can escape on that well-deserved holiday now.
  • No-deposit holidays: When you want to jump on an awesome deal but don’t have the full amount yet, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Chianti Region Expedia holiday?
Yes — and it’s simple too. Expedia has access to more than 400 partner airlines globally. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.

Discover the most popular places to visit in Chianti Region

Meleto Castle

Meleto Castle

Find out about the history of Gaiole in Chianti when you take a trip to Meleto Castle. Discover the beautiful countryside in this walkable area or enjoy its local tours.

Meleto Castle
Castellina in Chianti which includes farmland

Buondonno Winery

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 quaint area.

Buondonno Winery

Antinori nel Chianti Classico

4/5(1 review)

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the stunning cathedral and wineries in this walkable area.

Antinori nel Chianti Classico

Unmissable things to do in Chianti Region

Chianti Wineries Tour with Food and Wine Tasting from Florence

Chianti Wineries Tour with Food and Wine Tasting from Florence

£75
per adult
Chianti Wineries Tour with Food and Wine Tasting from Florence
Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

£75
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
Siena, San Gimignano and Chianti Full Day Trip with Wine Tastings

Chianti, San Gimignano and Siena Full Day Trip with Wine Tastings

£132
per adult
Chianti, San Gimignano and Siena Full Day Trip with Wine Tastings
See all activities in Chianti Region

* 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.