Chianti Region Vacation Packages 2025 from $1,211

Chianti Region flight + hotel vacation packages

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

Tenuta di Artimino Member of Meliá Collection

per person

Jul 22 - Jul 27

found 1 day ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

This Tuscan-style hotel features an attached winery, a full-service spa, and 2 restaurants. There's fun for all ages with a playground and an arcade/game room, and babysitting is an added bonus. Enjoy the outdoor tennis court and perks like free self parking and free WiFi.

Precise Tale Poggio Alla Sala

Save 100% on your flight

per person

Jul 22 - Jul 27

found 1 day ago

Roundtrip 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.

Castello di Spaltenna- Small Luxury Hotels of the World

Save 100% on your flight

per person

Aug 2 - Aug 9

found 18 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

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.

Hotiday Room Collection - Marinetta

Save 100% on your flight

per person

Aug 2 - Aug 9

found 18 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

This smoke-free hotel's full-service spa and 2 outdoor pools are some of the highlights. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking. Free WiFi in public areas, a terrace, and luggage storage are also on offer.

ADLER Spa Resort Thermae

Save 100% on your flight

per person

Jul 22 - Jul 27

found 1 day ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

This smoke-free hotel features an attached winery, a full-service spa, and hot springs. There's fun for all ages with a free kid's club and a playground, and barbecue grills are available on site. Enjoy the 2 outdoor pools and free perks like cooked-to-order breakfast and valet parking.

Top Chianti Region hotels deals

Hotel Borgo di Cortefreda Relais

Via Roma 191, Barberino Tavarnelle, FI

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$140 total

Jun 2 - Jun 3

Total includes taxes and fees

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.

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

$441 nightly

$497 total

Jun 6 - Jun 7

Total includes taxes and fees

Pool

Breakfast included

Hu Norcenni Girasole Village

Via Norcenni 7, Figline e Incisa Valdarno, FI

$60 nightly

$70 total

Jun 5 - Jun 6

Total includes taxes and fees

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.

Pool

Hot Tub

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$80 total

Jun 22 - Jun 23

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

Pet friendly

Free WiFi

Hotel Le Pozze Di Lecchi

Loc. Molinaccio, Gaiole in Chianti, SI

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$134 total

Jun 5 - Jun 6

Total includes taxes and fees

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

Borgo Vescine

Località Vescine, Radda in Chianti, SI

Free Cancellation

Reserve now, pay when you stay

$356 nightly

$401 total

Jun 4 - Jun 5

Total includes taxes and fees

An attached winery, 2 restaurants, and an outdoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and airport shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like buffet 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.

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 $1,211. 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.