Chianti Region Vacation Packages 2026 from $1,288

Chianti Region flight + hotel vacation packages

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

Boutique Hotel del Corso

Historic Centre of Florence

$1,288

per person

Oct 15 - Oct 20

found 16 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

Free WiFi in public areas, a library, and a safe deposit box are available at this hotel. Concierge services are provided for your convenience.

Precise Tale Poggio Alla Sala

Save 100% on your flight

$2,877

per person

Sep 29 - Oct 4

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.

Eurostars Florence Boutique

Historic Centre of Florence

$1,631

per person

Sep 27 - Oct 3

found 18 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This hotel features a 24-hour gym and a rooftop terrace. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, express check-out, and a computer station are also on offer.

L'Andana

$2,274

per person

Oct 11 - Oct 17

found 1 day ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

This luxury hotel features an attached winery, a full-service spa, and 2 restaurants. There's fun for all ages with a free kid's club and mini golf, and complimentary bicycles are available on site. Enjoy the 2 outdoor pools and free perks like buffet breakfast and free self parking.

Hotel Regency

Historic Centre of Florence

Save 100% on your flight

$2,599

per person

Oct 11 - Oct 17

found 1 day ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Enjoy the free buffet breakfast each morning.

Top Chianti Region hotels deals

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$77 total

Aug 5 - Aug 6

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 I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$121 total

Jul 29 - Jul 30

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.

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$391 nightly

$441 total

Aug 9 - Aug 10

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

Free Cancellation

Reserve now, pay when you stay

$209 nightly

$229 total

Jul 30 - Jul 31

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 Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$171 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.

Borgo Vescine

Località Vescine Radda in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$454 nightly

$509 total

Jul 28 - Jul 29

Total with 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.

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 $1,288. 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.