Chianti Region Vacation Packages

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Your Chianti Region Vacation

Lock in a vacation package to Chianti Region and enjoy what it means to travel on your own terms. You'll be charmed by its walking trails, cycling and views. Start your trip to Chianti Region with some time exploring San Gimignano visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Gaiole in Chianti is another city that draws travellers from near and far. Castello di Albola and Meleto Castle are two of the leading places to see in this destination. If you're ready to stop dreaming and start travelling, Expedia will help turn your Chianti Region vacation into reality.

Top Chianti Region Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Santa Croce
per person
Jul. 20 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.8/10 Good! (1,006 reviews)
Nice and clean room, good sheets and towels. Staff very nice, they allow to leave your luggage after checkout and come pick it up later.

Reviewed on Apr. 29, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Santa Maria Novella
per person
Jul. 12 - Jul. 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (436 reviews)
Wonderful stay. Staff very warm and friendly. Celebrating daughter's birthday, they offered a bottle of prosecco but we can't handle our booze in such quantity so we got some lovely juice drinks. The rooms are spotless, bedding and linens top quality, location is very quiet. Breakfast was excellent with a very large selection of items. We did not have room for the hot selections but they looked delicious. Wish we could have stayed more than one night, will certainly be our top choice for our next stay. Location is very walkable to the main train station and to the city center, but set back enough that you have a quiet neighborhood feel.

Reviewed on Apr. 26, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Duomo
per person
Jul. 20 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (1,002 reviews)
We couldn’t be happier with the location, the staff, the rooms, the dining options, and the views from the rooftop bar. Amazing!

Reviewed on Apr. 29, 2025

Glance Hotel In Florence

Glance Hotel In Florence

4 out of 5
San Lorenzo
per person
Jun. 5 - Jun. 11
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Staff very helpful and friendly. Room was clean and modernized. Unbelievable view from rooftop pool area. Walking distance to just about everything. Even walked to and from Piazzale Michelangelo.

Reviewed on Apr. 19, 2025

Hotel Santa Maria Novella

Hotel Santa Maria Novella

4 out of 5
Santa Maria Novella
per person
Jun. 5 - Jun. 11
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (1,004 reviews)
Excellent location Clean Great stai

Reviewed on Apr. 27, 2025

Ready to book your vacation to Chianti Region?

 

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Chianti Region Hotel Deals

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 CA $180 per night from May 12 to May 13
CA $180
CA $208 total
includes taxes & fees
May 12 - May 13
9.2/10 Wonderful! (407 reviews)
"Great location. Amazing and helpful staff. Highly recommend"

Reviewed on Apr. 20, 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
The price is CA $556 per night from May 15 to May 16
CA $556
CA $627 total
includes taxes & fees
May 15 - May 16
9.4/10 Exceptional! (221 reviews)
"Great spot. Terrace restaurant decent but food was served cold and undercooked. Bar pours a little light."

Reviewed on Apr. 29, 2025

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 CA $93 per night from May 11 to May 12
CA $93
CA $112 total
includes taxes & fees
May 11 - May 12
8/10 Very Good! (443 reviews)
"Very good property"

Reviewed on Sep. 26, 2024

Hotel Ristorante Alcide
See all 5,057 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chianti Region vacation package cost?
Live it up in Chianti Region from as low as CA $1,760. 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.

Discover the most popular places to visit in Chianti Region

Castellina in Chianti showing farmland

Buondonno Winery

You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area.

Buondonno Winery

Tenuta Torciano Winery

5/5(1 review)

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this relaxing area.

Tenuta Torciano Winery

Montegufoni Castle

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

Montegufoni Castle

What to do in Chianti Region

Chianti Wineries Tour with Food and Wine Tasting from Florence

Chianti Wineries Tour with Food and Wine Tasting from Florence

CA $138
per adult
Chianti Wineries Tour with Food and Wine Tasting from Florence
Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

CA $138
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
Siena, San Gimignano and Chianti Full Day Trip with Wine Tastings

Chianti, San Gimignano and Siena Full Day Trip with Wine Tastings

CA $242
per adult
Chianti, San Gimignano and Siena Full Day Trip with Wine Tastings
See all activities in Chianti Region
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.