Chianti Region Holidays from £474

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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.

Top Chianti Region Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
LHP River Club

LHP River Club

5 out of 5
Santa Croce
per person
11 Oct - 16 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
No reviews
Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
10 Sept - 17 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on 18 Jul 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
5 Sept - 12 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
The property is very centrally located—just a short walk from the Duomo and the central train station, with easy access to the tram as well. I was pleasantly surprised by how convenient the location was. The staff were friendly, and the included breakfast was a nice way to start the day with a quick bite. The only suggestion I’d make is to provide a thicker blanket for added comfort.

Reviewed on 29 Jul 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
per person
10 Sept - 17 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (98 reviews)
The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the room for me right away. Highly recommended for beauty, serene peace and quiet

Reviewed on 19 Jul 2025

Chianti Region Essential Information

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

Top hotels in Chianti Region

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
The price is £343 per night from 10 Aug to 11 Aug
£343
10 Aug - 11 Aug
includes taxes & fees
9.4/10 Exceptional! (237 reviews)
"This is truly my favorite place in the world—peaceful, beautiful, and filled with the kindest staff. I’m so glad we found it. I didn’t want to leave and joked with my family that I might just run away and stay forever. The location and scenery are absolutely stunning. We enjoyed fantastic meals during ..."

Reviewed on 16 Jul 2025

Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Fully refundableReserve now, pay when you stay
The price is £117 per night from 1 Aug to 2 Aug
£117
1 Aug - 2 Aug
includes taxes & fees
9.2/10 Wonderful! (434 reviews)
Adults don’t want baby food!
"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken ..."

Reviewed on 28 Jul 2025

Hotel Borgo di Cortefreda Relais
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
The price is £51 per night from 3 Aug to 4 Aug
£51
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (449 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on 7 Jul 2025

Hotel Ristorante Alcide
See all 5,193 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.
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Popular places to visit

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

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

The Mall Luxury Outlet

4/5(18 reviews)

During your visit to Reggello, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and churches in this walkable area.

The Mall Luxury Outlet

What to do in Chianti Region

Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

£74
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
Chianti Wineries Tour with Food and Wine Tasting from Florence

Chianti Wineries Tour with Food and Wine Tasting from Florence

£74
per adult
Chianti Wineries Tour with Food and Wine Tasting from Florence
Vintage Fiat 500 Tuscany Drive with Winery Lunch

Vintage Fiat 500 Tuscany Drive with Winery Lunch

£129
per adult
90% of travellers recommend
Vintage Fiat 500 Tuscany Drive with Winery Lunch
See all activities in Chianti Region

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.

* 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.