Chianti Region Holidays

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Chianti Region Holiday

Our pick of the best Chianti Region Hotel Deals

Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
The price is NZ$137 per night from 16 July to 17 July
NZ$137
16 July - 17 July
includes taxes & fees
8.2/10 Very good! (350 reviews)
"Room was clean, staff was helpful and easy to park."

Reviewed on 27 June 2026

Hotel Toscana Ambassador
Castello Vicchiomaggio

Castello Vicchiomaggio

Via Vicchiomaggio, 4 Greve in Chianti FI
Fully refundableReserve now, pay when you stay
The price is NZ$335 per night from 12 July to 13 July
NZ$335
12 July - 13 July
includes taxes & fees
9.4/10 Exceptional! (396 reviews)
"Absolutely stunning building and grounds, our room was beautiful and full of character."

Reviewed on 24 June 2026

Castello Vicchiomaggio
Relais Villa Olmo

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI
Fully refundableReserve now, pay when you stay
The price is NZ$377 per night from 22 July to 23 July
NZ$377
22 July - 23 July
includes taxes & fees
9.4/10 Exceptional! (248 reviews)
"Beautiful property."

Reviewed on 28 June 2026

Relais Villa Olmo
See all 4,922 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.

Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

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.
See properties

What to do in Chianti Region

Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-Group Wine Tasting Experience in the Tuscan Countryside

NZ$176
per adult
98% of travellers recommend
Small-Group Wine Tasting Experience in the Tuscan Countryside
Skip-the-Line Duomo: Priority-Access 30-Minute Guided Tour

Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

NZ$39
per adult
82% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

NZ$32
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
See all activities in Chianti Region

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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.