Chianti Region Holidays & Package Deals

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Chianti Region Holiday

Our pick of the best Chianti Region Hotel Deals

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Fully refundableReserve now, pay when you stay

NZ$129

23 Aug - 24 Aug

includes taxes & fees

8.2/10 Very good! (359 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

NZ$326

20 Sept - 21 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

NZ$710

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

See all 4,898 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 stunning cathedral and wineries in this walkable area.

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A grand, illuminated building with arched windows and a central fountain.

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.

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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.

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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.

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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.

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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.

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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.

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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.

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What to do in Chianti Region

Express Pasta & Tiramisù Small Group Cooking Class With Unlimited Wine

NZ$69

per adult

88% of travellers recommend

Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour

NZ$96

per adult

96% of travellers recommend

Accademia timed-entry Ticket with Instant Delivery & Priority Access

NZ$81

per adult

94% of travellers recommend

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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Car hire Greve in Chianti

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

Chianti Region Holidays

Book a Hotel + Flight or Car together to unlock savings

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Find the right fit

Rest easy