Chianti Region Holidays
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Where to stay in Chianti Region
Find the best Chianti Region areas and neighborhoods for the activities you enjoy most. Learn more about Chianti Region
Tavarnelle Val di Pesa
Tavarnelle Val di Pesa is noteworthy for its wineries, and you can make a stop at top attractions like Passignano Abbey and Abbey of Passignano.
Barberino Val d'Elsa
Barberino Val d'Elsa is noteworthy for its wineries, and you can make a stop at top attractions like Casa Sola - Chianti Winery and Castello di Monsanto.
San Donato in Poggio
Travellers like the restaurants in San Donato in Poggio, and Pieve di San Donato in Poggio is a top attraction you might want to visit.
Certaldo Alto
You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Palazzo Pretorio or Casa del Boccaccio.
Sambuca
While Sambuca may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Abbey of Passignano and Passignano Abbey.
Top hotels in Chianti Region
Villa I Barronci Resort & Spa
Via Sorripa 10 San Casciano in Val di Pesa FI
Fully refundableReserve now, pay when you stay
Rp2.855.020
Rp3.263.463 total
6 Oct - 7 Oct
includes taxes & fees
Fattoria di Vegi
Località Vegi, 16 Castellina in Chianti SI
Fully refundableReserve now, pay when you stay
Rp5.436.236
Rp6.102.780 total
29 Sept - 30 Sept
includes taxes & fees
10/10 Exceptional! (18 reviews)
"Amazing! I wish I could have stayed forever!"
Reviewed on 4 Sept 2026
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
Rp7.041.153
Rp7.950.170 total
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 churches 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 wineries 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.
Castello di Radda Winery
9.2/10 (12 reviews)
You can enjoy a tasting or tour at Castello di Radda Winery during your travels to Radda in Chianti. 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
Florence: Pasta Cooking Class with Unlimited Wine
Rp329.881
per adult
94% of travellers recommend
Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour
Rp1.010.055
per adult
96% of travellers recommend
Best of Florence Tour with David at Accademia & Duomo (with VIP option)
Rp1.298.907
per adult
96% of travellers recommend
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
