Chianti Region Vacations

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Find the Best Chianti Region Vacation Packages

Chianti Region Hotel Deals

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! (240 reviews)
"This is truly my favorite place in the world—peaceful, beautiful, and filled with the kindest staff. I’m so glad we found it. I didn’t want to leave and joked with my family that I might just run away and stay forever. The location and scenery are absolutely stunning. We enjoyed fantastic meals during ..."

Reviewed on 2025/7/16

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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
Fully refundableReserve now, pay when you stay
The price is NT$1,847 per night from Aug 20 to Aug 21
NT$1,847
NT$2,240 total
Aug 20 - Aug 21
includes taxes & fees
8/10 Very Good! (450 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on 2025/7/7

Hotel Ristorante Alcide
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 NT$5,363 per night from Aug 28 to Aug 29
NT$5,363
NT$6,107 total
Aug 28 - Aug 29
includes taxes & fees
9.4/10 Exceptional! (436 reviews)
Adults don’t want baby food!
"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken ..."

Reviewed on 2025/7/28

Hotel Borgo di Cortefreda Relais
See all 5,172 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.

Discover the most popular places to visit in Chianti Region

Tenuta Torciano Winery

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.

Tenuta Torciano Winery

Montegufoni Castle

4/5(2 reviews)

Find out about the history of Montegufoni with a stop at Montegufoni Castle. Visit the stunning cathedral and notable monuments in this walkable area.

Montegufoni Castle

Isole e Olena Winery

You can enjoy a tasting or tour at Isole e Olena Winery during your travels to Barberino Val d'Elsa. Discover the beautiful countryside in this relaxing area, or enjoy its local tours.

Isole e Olena Winery

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