Chianti Region Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chianti Region

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 4.376.121 ₫ per night from 23 Jun to 24 Jun
4.376.121 ₫
4.994.383 ₫ total
23 Jun - 24 Jun
includes taxes & fees
9.2/10 Wonderful! (419 reviews)
"The pool was very nice overlooking the hills of Tuscany. The hotel has a nice ambience, rustic but very clean an updated. I like there were big windows that could open to a garden from the room. Getting around was a bit difficult even with a car. Very steep hills and is not so walkable. Very windy ..."

Reviewed on 7 Jun 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
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (226 reviews)
"Amazing place and amazing staff. We had the Most relaxing time. Loved the place and we are coming back for sure."

Reviewed on 9 Jun 2025

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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
The price is 1.915.983 ₫ per night from 21 Jul to 22 Jul
1.915.983 ₫
2.288.232 ₫ total
21 Jul - 22 Jul
includes taxes & fees
8/10 Very Good! (447 reviews)
"Room was nice and spacious. Air conditioner barely kept up with the heat. Had mosquitoes in the room the second night and don’t know how it got in the room. Overall all it’s a decent place to stay."

Reviewed on 28 May 2025

Hotel Ristorante Alcide
See all 5,147 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.

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 1null000null000 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.

Popular places to visit

Alta Val d'Elsa River Park

Alta Val d'Elsa River Park

Explore the great outdoors at Alta Val d'Elsa River Park, a lovely green space in Colle di Val d'Elsa. Discover the countryside and spas in this quaint area.

Alta Val d'Elsa River Park

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 stunning cathedral in this walkable area.

The Mall Luxury Outlet