Chianti Region Vacations 2025 from CA $2,028

Chianti Region flight + hotel packages

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

Aurum Uffizi

Santa Croce

Save 100% on your flight

per person

Jun. 3 - Jun. 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star 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 Historic Centre of Florence are located nearby.

The Moon Boutique Hotel & Spa

Santa Maria Novella

Save 100% on your flight

per person

Jun. 3 - Jun. 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star 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 Historic Centre of Florence and Cathedral of Santa Maria del Fiore are located nearby.

Dimora Palanca Boutique & SPA

Santa Maria Novella

per person

Jun. 26 - Jul. 2

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 5-star luxury hotel in Florence. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Historic Centre of Florence and Cathedral of Santa Maria del Fiore are located nearby.

Art Hotel Villa Agape

Oltrarno

Save 100% on your flight

per person

Jun. 3 - Jun. 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star hotel in Florence. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Uffizi Gallery and Historic Centre of Florence are located nearby.

Villa Neroli

Coverciano

per person

Jun. 26 - Jul. 2

found 21 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 free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Historic Centre of Florence 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

CA $145

CA $169 total

includes taxes & fees

May 12 - May 13

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.

Pool

Breakfast included

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13, Gaiole in Chianti, SI

Free cancellation

Reserve now, pay when you stay

CA $588

CA $663 total

includes taxes & fees

Apr 30 - May 1

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.

Pool

Breakfast included

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Free cancellation

Reserve now, pay when you stay

CA $93

CA $112 total

includes taxes & fees

May 11 - May 12

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.

Pet-friendly

Free WiFi

Il Borro - Relais & Châteaux

Località Borro, 1, San Giustino Valdarno, Loro Ciuffenna, AR

Free cancellation

Reserve now, pay when you stay

CA $762

CA $838 total

includes taxes & fees

May 6 - May 7

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

COMO Castello Del Nero

Strada Spicciano 7, Barberino Tavarnelle, FI

Free cancellation

Reserve now, pay when you stay

CA $1,648

CA $1,825 total

includes taxes & fees

Apr 28 - Apr 29

Stay at this 5-star luxury hotel in Barberino Tavarnelle. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Antinori nel Chianti Classico and Santa Lucia al Borghetto Church are located nearby.

Pool

Breakfast included

Villa I Barronci Resort & Spa

Via Sorripa 10, (GPS: Via Empolese), San Casciano in Val di Pesa, FI

Free cancellation

Reserve now, pay when you stay

CA $188

CA $216 total

includes taxes & fees

May 4 - May 5

Stay at this 4-star luxury hotel in San Casciano in Val di Pesa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Antinori nel Chianti Classico and Monastary of Sorelle Clarisse are located nearby.

Pool

Hot tub

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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 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 $2,028. 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.