Chianti Region Vacation Packages 2026 from $1,225

Chianti Region flight + hotel vacation packages

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

Grand Universe Lucca, Autograph Collection

Lucca Historical Center

$1,225

per person

Nov 1 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a terrace, and a garden are also on offer.

Villa Cora

Oltrarno

Save 100% on your flight

$2,786

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking and a free area shuttle.

Aurum Uffizi

Historic Centre of Florence

$1,308

per person

Oct 23 - Oct 29

found 21 hours ago

Roundtrip flight included

New York (JFK) 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.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,370

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A coffee shop, a terrace, and dry cleaning are also on offer.

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence

$1,603

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Florence (FLR)

This hotel features a bar/lounge, free WiFi in public areas, and a snack bar/deli. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Top Chianti Region hotels deals

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$345 nightly

$387 total

Oct 12 - Oct 13

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

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$203 total

Oct 8 - Oct 9

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

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

$399 nightly

$450 total

Oct 5 - Oct 6

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

Relais Vignale & Spa

Via Pianigiani 9 Radda in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$233 total

Oct 8 - Oct 9

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the seasonal outdoor pool and perks like free self parking.

Pool

Hot Tub

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI

Free Cancellation

Reserve now, pay when you stay

$929 nightly

$1,031 total

Oct 6 - Oct 7

Total with taxes and fees

A full-service spa, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free hotel. Families will appreciate the playground, kid-friendly dining, and babysitting. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Park Hotel Chianti

Via Michelangelo, 5 Barberino Tavarnelle FI

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$113 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel features a bar/lounge, a poolside bar, and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, a library, and a hair salon are also on offer.

Pool

Pet friendly

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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 $1,225. 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.