Chianti Region Vacation Packages 2026 from $1,015

Chianti Region flight + hotel vacation packages

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

Residenza Florentia

Historic Centre of Florence

Save 100% on your flight

$1,015

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) 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.

Hotel La Gemma

Historic Centre of Florence

Save 100% on your flight

$2,136

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This smoke-free hotel features a full-service spa and 2 restaurants. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Valet parking and luggage storage are also offered on site.

Hotel Balestri

Historic Centre of Florence

$1,417

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This hotel features a rooftop terrace and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.

FH55 Hotel Calzaiuoli

Historic Centre of Florence

$1,407

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This hotel features a coffee shop, concierge services, and valet parking. WiFi in public areas is free. Express check-in, dry cleaning, and luggage storage are also on offer.

Loggiato dei Serviti

Historic Centre of Florence

$1,205

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

A coffee shop, free WiFi in public areas, and luggage storage are available at this hotel. There's a safe deposit box and multilingual staff can provide around-the-clock assistance.

Top Chianti Region hotels deals

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$51 nightly

$56 total

Jan 4 - Jan 5, 2026

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

Pet friendly

Free WiFi

Hotel Borgo di Cortefreda Relais

Via Roma 191 Barberino Tavarnelle FI

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$101 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

This Tuscan-style hotel features a full-service spa and a restaurant. Families will appreciate the children's pool, picnic area, and in-room childcare. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Pool

Spa

Villa La Borghetta Resort

Via del Cesto Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

Get rates

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Enjoy the hot tub and perks like free WiFi.

Pool

Hot Tub

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$75 total

Jan 5 - Jan 6, 2026

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

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$116 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

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

Pool

Spa

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI

Get rates

An attached winery and a restaurant are featured at this smoke-free residence. Families will appreciate the onsite laundry facilities and in-room childcare. Enjoy the seasonal outdoor pool and free perks like 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.

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.

Castellina in Chianti which includes farmland

Buondonno Winery

You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area.

Antinori nel Chianti Classico

5/5(1 review)

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.

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $1,015. 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.