Chianti Region Vacation Packages 2025 from $966

Chianti Region flight + hotel vacation packages

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

Hotel Borgo di Cortefreda Relais

per person

Aug 31 - Sep 5

found 18 hours ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

The Sense Experience Resort

Save 100% on your flight

per person

Jul 11 - Jul 18

found 1 day ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

A private beach, 3 restaurants, and an outdoor tennis court are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and complimentary bicycles are available on site. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Orto De Medici Hotel

Historic Centre of Florence

per person

Aug 7 - Aug 9

found 12 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

This hotel features free WiFi in public areas, laundry facilities, and valet parking. A terrace, a garden, and a library are also on offer.

Hotel Garibaldi Blu

Historic Centre of Florence

per person

Aug 6 - Aug 9

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms and airport shuttle. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Hotel Pendini

Historic Centre of Florence

per person

Aug 7 - Aug 9

found 12 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

A bar/lounge and a 24-hour front desk are featured at this hotel, along with valet parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. Express check-out, dry cleaning, and luggage storage are also on offer.

Top Chianti Region hotels deals

Hotel Borgo di Cortefreda Relais

Via Roma 191, Barberino Tavarnelle, FI

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A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Free Cancellation

Reserve now, pay when you stay

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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. Self parking, a terrace, and a snack bar/deli are also offered.

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13, Gaiole in Chianti, SI

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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.

Hotel Le Pozze Di Lecchi

Loc. Molinaccio, Gaiole in Chianti, SI

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A full-service spa, an outdoor pool, and a restaurant are all featured at this Tuscan-style hotel. Enjoy the sauna and free perks like buffet breakfast and free self parking. A bar/lounge, a poolside bar, and a terrace are also provided.

Pool

Breakfast included

Hu Norcenni Girasole Village

Via Norcenni 7, Figline e Incisa Valdarno, FI

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This smoke-free campground features free water park access, an attached winery, and a nightclub. There's fun for all ages with a lazy river and a free kid's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free self parking and free train station pick-up.

Hotel Villa Cesi

via delle terre bianche 1, Impruneta, FI

Free Cancellation

Reserve now, pay when you stay

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A full-service spa, a 24-hour gym, and a restaurant 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 seasonal outdoor pool and perks like free self parking.

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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

Castello di Meleto, Gaiole in Chianti, Tuscany

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.

Cascate del Diborrato - Parco fluviale dell'Elsa

Inside the residential area of Colle Val d'Elsa is a historic and natural landscape of enormous value thanks to the Elsa River which crosses the Val d'Elsa creating a unique territory. The river creates enchanting corners for hiking and observing: the engineering works for gathering water, the artifical canal system for carrying the water to the city, the caves. A particularly suggestive point is the Diborrato water falls, a 15m jump which is more than 10m deep, a sort of small lake where the locals used to go to cool off. Other places not to miss are the Grotta dell'Orso, the Conchina, the Masso Bianco, the Nicchia and the Spianata dei Falchi, each with its own particularities. This natural richness has been recognized with the institution of a protected area in the River Park of the Upper Val d'Elsa which includes the path of the river from the city of Colle Val d'Elsa which stretches from Ponte Santa Giulia to Ponte di Spugna and includes the Caldane, thermal springs which were known to the Etruscans and Romans.

Alta Val d'Elsa River Park

Explore the great outdoors at Alta Val d'Elsa River Park, a lovely green space in Colle di Val d'Elsa. Discover the countryside and spas in this quaint area.

The Mall Luxury Outlet

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 $966. 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.