Chianti Region Vacation Packages 2026 from $914

Chianti Region flight + hotel vacation packages

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

Grand Hotel Cavour

Historic Centre of Florence

$914

per person

Jan 19 - Jan 24

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a gym and a rooftop terrace. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Aurum Uffizi

Historic Centre of Florence

$1,132

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Enjoy the free buffet breakfast each morning. A snack bar/deli and a safe deposit box are also provided.

Aurum Firenze

Historic Centre of Florence

$1,099

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

Free WiFi in public areas and a safe deposit box are available at this hotel. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Hotel Duomo Firenze

Historic Centre of Florence

$971

per person

Jan 19 - Jan 24

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

A bar/lounge and a 24-hour front desk are featured at this hotel, along with self parking. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.

Monastero di Cortona Hotel & Spa

Cortona Old Town

$1,181

per person

Dec 7 - Dec 12

found 18 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

A full-service spa and an indoor pool are featured at this luxury hotel. Enjoy the hot tub and free perks like full breakfast and WiFi in public areas. You'll appreciate the sauna, bar/lounge, and snack bar/deli.

Top Chianti Region hotels deals

hu Firenze Certosa camping in town

Via San Cristofano 2 Impruneta FI

Free Cancellation

Reserve now, pay when you stay

$32 nightly

$38 total

Nov 5 - Nov 6

Total with taxes and fees

This campground features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop is provided and the front desk is staffed around-the-clock.

Pool

Pet friendly

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$71 total

Nov 27 - Nov 28

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and a terrace are also offered.

Parking included

Free WiFi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI

$242 nightly

$273 total

Oct 30 - Oct 31

Total with taxes and fees

An attached winery and a restaurant are featured at this Tuscan-style hotel. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas. You'll appreciate the a rooftop terrace, bar/lounge, and snack bar/deli.

Pool

Breakfast included

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

$330 nightly

$374 total

Oct 30 - Oct 31

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$87 total

Nov 27 - Nov 28

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate kid-friendly dining and in-room childcare, along with mountain biking. Enjoy the a rooftop terrace and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Salvadonica - Borgo del Chianti

Via Grevigiana, 82 San Casciano in Val di Pesa FI

$68 nightly

$80 total

Nov 9 - Nov 10

Total with taxes and fees

An attached winery and an outdoor pool are featured at this smoke-free farm stay. Families will appreciate the bowling alley, onsite laundry facilities, and in-room childcare. Enjoy a meal from the restaurant and perks like free full breakfast and free self parking.

Pool

Breakfast included

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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.

Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)

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.

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Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $914. 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.