Chianti Region Vacations from $677

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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 travelers 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 traveling, Expedia will help turn your Chianti Region vacation into reality.

The Latest Chianti Region vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Tenuta di Artimino Member of Meliá Collection
Villa di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala
 La Bagnaia Golf Resort
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Discover the most popular places to visit in Chianti Region

What to do in Chianti Region

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
$149 nightly
The price is $171 total per night from Jul 6 to Jul 7
$171 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (425 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
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
$396 nightly
The price is $447 total per night from Jul 20 to Jul 21
$447 total
Jul 20 - Jul 21
Total includes taxes and fees
9.4/10 Exceptional! (229 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 Ristorante Alcide
Hotel Ristorante Alcide
4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $79 total per night from Jul 13 to Jul 14
$79 total
Jul 13 - Jul 14
Total includes taxes and fees
8/10 Very Good! (448 reviews)
"Room was nice and spacious. Air conditioner barely kept up with the heat. Had mosquitoes in the room the second night and don’t know how it got in the room. Overall all it’s a decent place to stay."

Reviewed on May 28, 2025

Hotel Ristorante Alcide
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.

Find the Best Chianti Region Vacation Packages

Chianti Region Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)

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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.