Chianti Region Vacations 2025 from CA $1,739

Chianti Region flight + hotel packages

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

Hotel Duomo Firenze

Historic Centre of Florence

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 3-star family-friendly hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Uffizi Gallery and Ponte Vecchio are located nearby.

Palazzo Firenze by Baglioni Hotels & Resorts

Historic Centre of Florence

per person

Aug 12 - Aug 17

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 5-star luxury hotel in Florence. Enjoy free breakfast, free WiFi, and 24-hour room service. Popular attractions Uffizi Gallery and Cathedral of Santa Maria del Fiore are located nearby.

San Firenze Suites & Spa

Historic Centre of Florence

per person

Aug 12 - Aug 17

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star spa hotel in Florence. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Uffizi Gallery and Cathedral of Santa Maria del Fiore are located nearby.

Cappuccina Country Resort

per person

Aug 2 - Aug 8

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star business-friendly hotel in San Gimignano. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Sant'Agostino Church and Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery are located nearby.

Hotel Roma

Historic Centre of Florence

per person

Jul 23 - Jul 29

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Historic Centre of Florence and Cathedral of Santa Maria del Fiore are located nearby.

Top Chianti Region hotels deals

Hotel Borgo di Cortefreda Relais

Via Roma 191, Barberino Tavarnelle, FI

Free cancellation

Reserve now, pay when you stay

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Stay at this 4-star spa hotel in Barberino Tavarnelle. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Santa Lucia al Borghetto Church and Abbey of Passignano are located nearby.

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Free cancellation

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Stay at this 4-star business-friendly hotel in Poggibonsi. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Church of San Lorenzo and Archeodromo di Poggibonsi are located nearby.

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13, Gaiole in Chianti, SI

Free cancellation

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Stay at this 5-star spa hotel in Gaiole in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Church of San Sigismondo and Gaiole in Chianti Stadium are located nearby.

Hu Norcenni Girasole Village

Via Norcenni 7, Figline e Incisa Valdarno, FI

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Stay at this 4-star spa campground in Figline e Incisa Valdarno. Enjoy free parking, 7 outdoor pools, and 3 restaurants. Popular attractions Franciscan Monastery of St. Francis and Museum of Terranuova Tuscany are located nearby.

Hotel Le Pozze Di Lecchi

Loc. Molinaccio, Gaiole in Chianti, SI

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Stay at this 4-star spa hotel in Gaiole in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Meleto Castle and Castello di Meleto Cantina are located nearby.

Borgo Vescine

Località Vescine, Radda in Chianti, SI

Free cancellation

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Stay at this 5-star luxury hotel in Radda in Chianti. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Castellina Fortress and Casa Vinicola Luigi Cecchi are located nearby.

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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.

Popular places to visit

Meleto Castle

Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Alta Val d'Elsa River Park

Explore the great outdoors at Alta Val d'Elsa River Park, a lovely green space in Colle di Val d'Elsa. Discover the countryside and spas in this quaint area.

The Mall Luxury Outlet

4/5(15 reviews)

During your visit to Reggello, you can search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene and stunning cathedral in this walkable area.

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only CA $1,739. Let Travelocity save you money and hassle with our awesome vacation package deals. With hotels, flights and tours all ready to go at our one-stop shop, why wait?

Where can I get the best vacation package deals for Chianti Region?

For an amazing Chianti Region package deal, turn to Travelocity. Take your pick of 400 partner airlines and 1,000,000 properties worldwide to create your ultimate trip — simple as that.

Why should I book my Chianti Region vacation package via Travelocity?

From our 24/7 customer support to our range of amazing destinations, we are committed to giving you the most unforgettable escape. All you need to do is click and book — our Price Match Guarantee will ensure you score the best price.

Will I save money on my Chianti Region car rental if I book it with hotels and flights?

Bundling your bookings into a Chianti Region vacation package will save you a tidy sum. You can bundle a car and flight; a hotel, car and flight; or a hotel and car. You won’t find a better way to discover the greater Chianti Region area than from the comfort of your own rental car. You can also add experiences and tours to your Travelocity package.

Which airport is best for Chianti Region?

Arranging where you land in Chianti Region is a breeze — most airlines fly in and out of Peretola Airport (FLR).

What is there to do in Chianti Region?

Chianti Region boasts hidden surprises around every turn, but be sure you get to Collegiate Church of Santa Maria Assunta and Antinori nel Chianti Classico while you’re here. These attractions can’t be missed.