Chianti Region Holidays
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Your Chianti Region Holiday
Lock in a holiday package to Chianti Region and enjoy what it means to travel on your own terms. You'll be charmed by its walking trails, cycling and views. Start your trip to Chianti Region with some time exploring San Gimignano visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Gaiole in Chianti is another city that draws travellers from near and far. Castello di Albola and Meleto Castle are two of the leading places to see in this destination. If you're ready to stop dreaming and start travelling, Expedia will help turn your Chianti Region holiday into reality.
Chianti Region Holiday
Chianti Region Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Galileo Galilei Airport (PSA) |
Top Sights | Sentierelsa Trail, Castelvecchio Natural Reserve and Valle dellInferno e Bandella |
Our pick of the best Chianti Region Hotel Deals
Hotel Toscana Ambassador
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
AU$110
23 Aug - 24 Aug
includes taxes & fees
8.2/10 Very good! (358 reviews)
"Room was clean, staff was helpful and easy to park."
Reviewed on 27 June 2026
Villa I Barronci Resort & Spa
Via Sorripa 10 San Casciano in Val di Pesa FI
Fully refundableReserve now, pay when you stay
AU$271
17 Sept - 18 Sept
includes taxes & fees
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
AU$590
6 Sept - 7 Sept
includes taxes & fees
9.6/10 Exceptional! (281 reviews)
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Reviewed on 4 Aug 2026
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.
Stay near popular Chianti Region attractions
Antinori nel Chianti Classico
9.4/10 (16 reviews)
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.
The Mall Luxury Outlet
8.8/10 (355 reviews)
During your visit to Leccio, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.
Tenuta Torciano Winery
9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
Castle of Brolio
9.2/10 (44 reviews)
You can find out about the history of Gaiole in Chianti with a visit to Castle of Brolio. Discover the beautiful countryside and cosy cafes in this walkable area.
Verrazzano Castle
9.8/10 (10 reviews)
You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.
Castello di Albola
9.0/10 (9 reviews)
You can enjoy a tasting or tour at Castello di Albola during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area or enjoy its local tours.
Piazza Matteotti
9.4/10 (21 reviews)
Find out about the history of Greve in Chianti with a stop at Piazza Matteotti. Discover the beautiful countryside in this quaint area or enjoy its local tours.
Meleto Castle
8.6/10 (10 reviews)
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.
What to do in Chianti Region
City Sightseeing Florence Hop-on Hop-off Bus Tour
AU$40
per adult
76% of travellers recommend
Florence Accademia Gallery Tour with Entrance Ticket Included
AU$78
per adult
92% of travellers recommend
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
AU$30
per adult
Frequently asked questions
How much does a Chianti Region holiday package cost?
Live it up in Chianti Region from as low as . Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of tours or experiences to your package.
How do I get a cheap travel package to Chianti Region?
Find flights that suit your busy schedule, add a hotel to your booking and watch how much you save with a Chianti Region holiday package. It's that easy! From flights and hotels to rental cars and activities, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1 000 000 properties around the world to pick from, you won't be short of choice.
Where should I stay in Chianti Region?
Val dElsa is in the top spot on many Chianti Region must-see lists. Collegiate Church of Santa Maria Assunta is one reason why.
What are the top hotels in Chianti Region?
When it comes to hotels in Val dElsa, Grand Hotel Baglioni and Hotel Spadai are among the favourites. If you're spending time in Greve in Chianti, Hotel Pendini and The Market Urban Hotel will make you feel at home.
How far in advance should I book my Chianti Region holiday?
While prices change from time to time, we generally suggest booking your flight as soon as possible. Many international airfares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Low prices to Chianti Region sometimes emerge only weeks before departure.
What does an Expedia Chianti Region travel package include?
Much of that is up to you. You can pick from a variety of Chianti Region packages, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Chianti Region holiday looks like, get set to save!
What should I know before booking a Chianti Region travel package?
When you book your flights, hotels and car rentals together, you'll pick up fantastic discounts. Whether you're organising a mountain getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Chianti Region Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines across the globe, so you have loads of choice when creating your Chianti Region adventure.
If I'm not able to travel, can I cancel my Chianti Region holiday package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region holiday package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge additional fees. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
Explore a world of travel with Expedia
- Villa Nemora
- Holiday Homes in Castellina in Chianti
- Casa Anita
- Detached villa with private pool and garden
- Fattoria di Vegi
- Isola SERENA Newly Expanded Private Luxury Villa
- Relais Villa Casalta
- Restored farmhouse in heart of chianti with swimming pool and tennis court.
- Castellina in Chianti Hotels
- Casa Maravilla 6 in Castelnuovo Berardenga
- Dievole Wine Resort
- Borgo San Felice Resort
- Villa Santa Maria 14
- Winery Hotels in Chianti Region
- Colle di Val d'Elsa Hotels
- 4 Bedroom Villa in Figline Valdarno
- Palagina la Dimora
- Villa Norcenni Aparthotel
- Campo al Sole
- Villa Gaia
- Villa Vistarenni
- Holiday Homes in Greve in Chianti
- Castello Di Montemasso
- Charming castle apartement with glorious views
- Foresteria Castello di Verrazzano
- Winery Hotels in Greve in Chianti
- Greve in Chianti Hotels
- Laquerciaestate
- Villa Beltrami 14
- Villa Belvedere in the heart of Chianti
- Mercatale Val di Pesa Hotels
- B&B in Montefioralle
- Il Poderino
- Panzano in Chianti Hotels
- Pietraviva Hotels
- Villa Ferdinando
- Villas in Poggibonsi
- Lgbt Welcoming Hotels in Ponte Agli Stolli
- Borgo Vescine
- Relais & Chateaux Hotels in Radda in Chianti
- Radda in Chianti Hotels
- Sambuca Hotels
- Salvadonica
- Apartments in Siena
- B&B in Siena
- Siena City Centre Hotels
- Siena Historical Center Hotels
- Cheap Hotels in Siena
- Hotel Palazzetto Rosso
- Hotels with Pool in Siena
- La Terrazza Sul Campo Rooming House
- Nh Hotels in Siena
- Palazzo Ravizza
- Villa Il Castagno Wine & Resort
- Winery Hotels in Siena
- Siena Hotels
- Villas in Siena
- Tavarnelle Val di Pesa Hotels
- Romignano wine farm. Your villa in TUSCANY.
- Hotels near The Mall Luxury Outlet
- Ulignano Hotels
- Villa A Sesta Hotels
- Visit Antella
- Visit Castellina in Chianti
- Castello di Albola
- Visit Chianti Region
- Fortezza Medicea
- Visit Greve in Chianti
- Isole e Olena Winery
- Visit Levane
- Meleto Holidays
- Visit Panzano in Chianti
- Piazza del Campo
- Piazza delle Erbe
- Visit Ponte Agli Stolli
- Radda in Chianti Holidays
- Visit Radda in Chianti
- Siena Cathedral
- Siena Holidays
- Visit Siena
- The Mall Luxury Outlet
- Car hire Barberino Val d'Elsa
- Car hire Bucine
- Car hire Castellina in Chianti
- Car hire Greve in Chianti
- Car hire Montevarchi
- Car hire Panzano in Chianti
- Car hire Poggibonsi
- Car hire Radda in Chianti
- Car hire San Giovanni Valdarno
- Car hire Siena
- Car hire Tavarnelle Val di Pesa
- Europcar Rental Cars in Siena
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
