Chianti Region Vacations

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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
A rural landscape with vineyards, rolling hills, and scattered houses.

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.

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A historic stone church with a bell tower, surrounded by well-maintained hedges and a stone wall.

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 della Paneretta.

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San Donato in Poggio

Travelers like the restaurants in San Donato in Poggio, and Pieve di San Donato in Poggio is a top attraction you might want to visit.

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A dilapidated brick structure with a chimney, surrounded by grass and trees.

Certaldo Alto

You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.

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Sambuca

If you're looking for some top things to see and do in Sambuca and surrounding area, you can visit Abbey of Passignano and Passignano Abbey.

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Find the Best Chianti Region Vacation Packages

Chianti Region Hotel Deals

Fattoria di Vegi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI
NT$9,631
NT$10,812 total
Oct 22 - Oct 23
includes taxes & fees
10/10 Exceptional! (27 reviews)
"All aspects were superb and I highly recommend Vegi to friends, family and others. Beautiful locale and facility aesthetics, very well appointed, and excellent service."

Reviewed on 2026/9/23

Fattoria di Vegi
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
Fully refundableReserve now, pay when you stay
NT$4,335
NT$4,986 total
Oct 23 - Oct 24
includes taxes & fees
Villa I Barronci Resort & Spa
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI
NT$12,478
NT$14,089 total
Oct 21 - Oct 22
includes taxes & fees
9.6/10 Exceptional! (287 reviews)
"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."

Reviewed on 2026/9/15

Castello di Spaltenna- Small Luxury Hotels of the World
See all 4,918 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. Check out the churches 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 search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene 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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Verrazzano Castle

9.8/10 (10 reviews)
You can find out about the history of Greve in Chianti with a trip to Verrazzano Castle. Discover the area's countryside and wineries.
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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 stop at Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area.
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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 spend time at 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 when you take a trip to Piazza Matteotti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
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Frequently asked questions

How much does a Chianti Region vacation 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 vacation 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 favorites. 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 vacation?
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 vacation 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 organizing 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 vacation 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 vacation package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region vacation 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.