Chianti Region Vacation Packages 2026 from $1,694

Chianti Region flight + hotel vacation packages

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

Eurostars Florence Boutique

Historic Centre of Florence

$1,694

per person

May 12 - May 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hotel Santa Maria Novella

Historic Centre of Florence

$2,563

per person

May 12 - May 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a gym and a rooftop terrace. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

Hotel L'Orologio Firenze

Historic Centre of Florence

$2,312

per person

May 12 - May 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a gym and a bar/lounge. WiFi in public areas is free. Self parking, a business center, and a coffee shop are also offered.

Hotel Balestri

Historic Centre of Florence

$2,156

per person

May 12 - May 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hotel degli Orafi

Historic Centre of Florence

$2,010

per person

Jun 29 - Jul 3

just found

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a rooftop terrace and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Chianti Region hotels deals

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

Free Cancellation

$68 nightly

$81 total

Apr 12 - Apr 13

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.

Borgo Vescine

Località Vescine Radda in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$462 nightly

$518 total

Apr 8 - Apr 9

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.

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$198 total

Apr 27 - Apr 28

Total with taxes and fees

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 buffet 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

$378 nightly

$427 total

Apr 10 - Apr 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.

Il Borro - Relais & Châteaux

Località Borro, 1 Loro Ciuffenna AR

Free Cancellation

Reserve now, pay when you stay

$632 nightly

$695 total

Apr 27 - Apr 28

Total with taxes and fees

An attached winery, 2 restaurants, and 2 outdoor tennis courts are all featured at this luxury farm stay. Enjoy the 24-hour gym and perks like free self parking and free WiFi. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$126 total

Apr 16 - Apr 17

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.

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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

A woman on a spiral stairway, part of the modern architecture at Antinori Winery Nel Chianti Classico, San Casciano in Val di Pesa, Tuscany, Italy.

Antinori nel Chianti Classico

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the stunning cathedral and wineries in this walkable area.

Night view of the architecture of the small town of Florence, Shanghai

The Mall Luxury Outlet

During your visit to Leccio, you can search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene and stunning cathedral in this walkable area.

Tenuta Torciano Winery

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this relaxing area.

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $1,694. 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.