Chianti Region Vacation Packages 2026 from $1,229

Chianti Region flight + hotel vacation packages

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

Aurum Firenze

Historic Centre of Florence

$1,229

per person

Oct 21 - Oct 26

found 5 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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.

Eurostars Florence Boutique

Historic Centre of Florence

$1,444

per person

Oct 21 - Oct 26

found 5 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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.

Aurum Uffizi

Historic Centre of Florence

$1,233

per person

Oct 21 - Oct 26

found 5 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,668

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Florence (FLR)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A coffee shop, a terrace, and dry cleaning are also on offer.

Hotel Caravaggio

Historic Centre of Florence

$1,478

per person

Oct 21 - Oct 26

found 5 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Florence (FLR)

A bar/lounge and a 24-hour front desk are featured at this hotel, along with valet parking. WiFi in public areas is free. A coffee shop, a terrace, and limo/town car service are also on offer.

Top Chianti Region hotels deals

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$92 total

Aug 22 - Aug 23

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

$136 nightly

$157 total

Aug 7 - Aug 8

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.

Pool

Hot Tub

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$396 nightly

$447 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.

Pool

Breakfast included

Castello Vicchiomaggio

Via Vicchiomaggio, 4 Greve in Chianti FI

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$224 total

Sep 1 - Sep 2

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

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$279 nightly

$314 total

Aug 24 - Aug 25

Total with taxes and fees

An attached winery and a restaurant are featured at this Tuscan-style hotel. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas. You'll appreciate the a rooftop terrace, bar/lounge, and snack bar/deli.

Pool

Breakfast included

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$171 total

Aug 27 - Aug 28

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.

Pool

Spa

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.

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.

See properties

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $1,229. 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.