Chianti Region Vacation Packages 2026 from $559

Chianti Region flight + hotel vacation packages

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

Aurum Firenze

Historic Centre of Florence

$559

per person

Jan 15 - Jan 20

found 10 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

Free WiFi in public areas and a safe deposit box are available at this hotel. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Aurum Uffizi

Historic Centre of Florence

$662

per person

Feb 22 - Feb 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Enjoy the free buffet breakfast each morning. A snack bar/deli and a safe deposit box are also provided.

The St. Regis Florence

Historic Centre of Florence

Save 100% on your flight

$1,810

per person

Jan 12 - Jan 17

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

This hotel features a restaurant, a hot tub, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport shuttle. There's a steam room on site, and laundry facilities and free newspapers are also offered.

Eurostars Florence Boutique

Historic Centre of Florence

$592

per person

Jan 15 - Jan 20

found 10 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Villa Cora

Oltrarno

$2,142

per person

Feb 21 - Feb 26

found 21 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking and a free area shuttle.

Top Chianti Region hotels deals

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$48 nightly

$52 total

Dec 14 - Dec 15

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.

Hotel Borgo di Cortefreda Relais

Via Roma 191 Barberino Tavarnelle FI

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$111 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 free perks like buffet breakfast and free self parking.

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

$67 nightly

$74 total

Dec 23 - Dec 24

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.

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$112 total

Dec 14 - Dec 15

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.

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Get rates

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.

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.

Don't see what you're looking for?

See all available properties in Chianti Region

View all properties

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 $559. 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.