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.
Cappuccina Country Resort

Cappuccina Country Resort

4 out of 5
per person
Aug 17 - Aug 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (69 reviews)
We absolutely loved our stay. I wish we got to stay longer. The hotel and the town are so lovely and peaceful. I could have easily stayed there for three days. The staff was so kind. The room was comfortable and very luxurious. Breakfast was yummy.

Reviewed on May 28, 2025

Collegio alla Querce - Auberge Resorts

Collegio alla Querce - Auberge Resorts

5 out of 5
Le Cure
Save 100% on your flight
per person
Aug 17 - Aug 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (1 review)
Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 22 - Sep 28
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location and lovely breakfast.

Reviewed on Jul. 9, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 18 - Sep 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
The staff is very friendly.

Reviewed on Jul. 11, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 21 - Sep 27
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (462 reviews)
Breakfast was very good and the staff were excellent. Expresso in the morning was on point.

Reviewed on Jul. 5, 2025

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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
The price is CA $536 per night from Aug 12 to Aug 13
CA $536
CA $606 total
Aug 12 - Aug 13
includes taxes & fees
9.4/10 Exceptional! (232 reviews)
"We stayed here as a family of six, including our two 3-year-olds, and it was by far our favorite place during our time in Italy! The kids absolutely loved swimming in the pools and running around the beautiful property. It felt peaceful, safe, and perfect. The breakfast was lovely each morning—fresh, ..."

Reviewed on Jun. 28, 2025

Castello di Spaltenna- Small Luxury Hotels of the World
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 $182 per night from Jul 13 to Jul 14
CA $182
CA $210 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (428 reviews)
"We were a group of 10 who just returned from a 4 night stay at this beautiful hotel. It exceeded our groups expectations. It is quaint, in a beautiful setting. The staff was excellent, accommodating any request that was made. Restaurant is very good, included breakfast was great, many choices. We ..."

Reviewed on Jun. 29, 2025

Hotel Borgo di Cortefreda Relais
Hotel Ristorante Alcide
Hotel Ristorante Alcide
4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundable
The price is CA $71 per night from Jul 13 to Jul 14
CA $71
CA $88 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (449 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 Jul. 7, 2025

Hotel Ristorante Alcide
See all 5,178 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

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 relaxing 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 quaint area.

Tenuta Torciano Winery

Montegufoni Castle

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

What to do in Chianti Region

VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti

VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti

CA $191
per adult
92% of travellers recommend
VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti
Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

CA $137
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
Siena: Horseback Adventure in the Tuscan Countryside

Siena: Horseback Adventure in the Tuscan Countryside

CA $112
per adult
Siena: Horseback Adventure in the Tuscan Countryside
See all activities in Chianti Region

Frequently asked questions

How much does a Chianti Region vacation package cost?
Live it up in Chianti Region from as low as CA $1,491. 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.