Chianti Region Vacations from $590

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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
Albergo Le Terme
Villa Tolomei Hotel & Resort
c-hotels Joy
Hotel degli Orafi
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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 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 $71 total per night from Oct 12 to Oct 13
$71 total
per night
Oct 12 - Oct 13
8/10 Very Good! (454 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
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 $424 total per night from Oct 26 to Oct 27
$424 total
per night
Oct 26 - Oct 27
9.4/10 Exceptional! (255 reviews)
"This hotel is wonderful with beautiful views from the terrace! The only complaint is the number of stairs you have to take if staying on upper floors (no elevator) - my husband has a bad back so that’s a consideration. Also, wish they would accommodate all the guests in the gourmet restaurant as ..."

Reviewed on Sep 27, 2025

Castello di Spaltenna- Small Luxury Hotels of the World
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

4 out of 5
Via Sorripa 10, (GPS: Via Empolese), San Casciano in Val di Pesa, FI
The price is $145 total per night from Nov 5 to Nov 6
$145 total
per night
Nov 5 - Nov 6
9.2/10 Wonderful! (398 reviews)
One of the best Hotels in Tuscany
"This magnificent Hotel exceeded all our expectations. The rooms were very generous is size and the beds were so comfy. Breakfast was exceptional too.... The heated swimming pool with Jacuzzi and the view of the countryside was breathtaking."

Reviewed on Oct 1, 2025

Villa I Barronci Resort & Spa
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.

Chianti Region Essential Information

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

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