Chianti Region Vacation Packages 2026 from $1,085

Chianti Region flight + hotel vacation packages

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

Aurum Firenze

Historic Centre of Florence

$1,085

per person

Sep 28 - Oct 3

found 11 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Precise Tale Poggio Alla Sala

Save 100% on your flight

$3,162

per person

Sep 6 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Family-friendly amenities include a playground and in-room childcare. Enjoy the 24-hour gym and free perks like buffet breakfast and WiFi in public areas.

Residenza Florentia

Historic Centre of Florence

$1,275

per person

Sep 28 - Oct 3

found 10 hours ago

Roundtrip non-stop flight included

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

This hotel features a bar/lounge, free WiFi in public areas, and express check-out. Luggage storage, concierge services, and a virtual front desk are also on offer.

Il Rivalta - Place of Charme

Historic Centre of Florence

Save 100% on your flight

$2,664

per person

Sep 20 - Sep 24

found 4 hours ago

Roundtrip non-stop flight included

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

The apartment's gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Valet parking, a garden, and a snack bar/deli are also offered.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

Save 100% on your flight

$2,034

per person

Sep 20 - Sep 24

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.

Top Chianti Region hotels deals

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$76 total

Jul 26 - Jul 27

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.

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$147 total

Jul 19 - Jul 20

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.

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$180 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features an attached winery, a full-service spa, and 2 restaurants. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the indoor pool and perks like free self parking.

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$393 nightly

$444 total

Aug 10 - Aug 11

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.

Castello Vicchiomaggio

Via Vicchiomaggio, 4 Greve in Chianti FI

$170 nightly

$187 total

Jul 19 - Jul 20

Total with taxes and fees

An attached winery and a restaurant are featured at this smoke-free farm stay. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A terrace, a garden, and wedding services are also on offer.

Pool

Parking included

Villa Il Palagio

Via Il Palagio 59 Rignano sull'Arno FI

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$138 total

Jul 19 - Jul 20

Total with taxes and fees

A nightclub and a restaurant are featured at this smoke-free apartment. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.

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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 $1,085. 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.