Chianti Region Vacations 2026 from CA $1,223

Chianti Region flight + hotel packages

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

Aurum Firenze

Historic Centre of Florence

CA $1,223

per person

Apr 14 - Apr 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

Stay at this hotel in Florence. Enjoy free breakfast, free WiFi, and a 24-hour front desk. 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.

Aurum Uffizi

Historic Centre of Florence

CA $1,273

per person

Apr 14 - Apr 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

Stay at this hotel in Florence. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Uffizi Gallery and Palazzo Vecchio are located nearby.

Art Atelier

Historic Centre of Florence

CA $1,599

per person

Mar 24 - Mar 30

found 1 hour ago

Roundtrip flight included

Calgary (YYC) to Florence (FLR)

Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Piazza del Duomo are located nearby.

Hotel Leonardo Da Vinci

Santa Maria Novella

CA $1,513

per person

Mar 24 - Mar 30

found 1 hour ago

Roundtrip flight included

Calgary (YYC) to Florence (FLR)

Stay at this hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Piazza del Duomo are located nearby.

The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $1,602

per person

Mar 24 - Mar 30

found 1 hour ago

Roundtrip flight included

Calgary (YYC) to Florence (FLR)

Book a stay at this spa hotel in Florence. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Ponte Vecchio are located nearby.

Top Chianti Region hotels deals

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

Free cancellation

Reserve now, pay when you stay

CA $73

CA $80 total

Feb 15 - Feb 16

includes taxes & fees

Book a stay at this business-friendly hotel in Poggibonsi. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Archeodromo di Poggibonsi and Poggio Imperiale Fortress are located nearby.

Pet-friendly

Free WiFi

Villa La Borghetta Resort

Via del Cesto Figline e Incisa Valdarno FI

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this spa hotel in Figline e Incisa Valdarno. Enjoy free WiFi, a full-service spa, and room service. Popular attractions Franciscan Monastery of St. Francis and Museum of Terranuova Tuscany are located nearby.

Pool

Hot tub

Hotel Borgo di Cortefreda Relais

Via Roma 191 Barberino Tavarnelle FI

Free cancellation

Reserve now, pay when you stay

CA $123

CA $145 total

Jan 25 - Jan 26

includes taxes & fees

Book a stay at this 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 Abbey of Passignano and Casa Sola - Chianti Winery are located nearby.

Pool

Spa

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this business-friendly hotel in Poggibonsi. Enjoy free WiFi, free parking, and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Archeodromo di Poggibonsi and Poggio Imperiale Fortress are located nearby.

Parking included

Free WiFi

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free cancellation

Reserve now, pay when you stay

CA $138

CA $155 total

Feb 10 - Feb 11

includes taxes & fees

Book a stay at this spa hotel in Figline e Incisa Valdarno. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Franciscan Monastery of St. Francis and Soffena Abbey are located nearby.

Pool

Spa

Il Borro - Relais & Châteaux

Località Borro, 1 Loro Ciuffenna AR

CA $784

CA $863 total

Feb 14 - Feb 15

includes taxes & fees

Book a stay at this golf farm stay in Loro Ciuffenna. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Il Borro Wines and La Salceta Winery are located nearby.

Pool

Spa

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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.

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 romantic area.

Antinori nel Chianti Classico

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the churches and wineries 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 $1,223. 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.