Chianti Region Vacation Packages 2026 from $1,292

Chianti Region flight + hotel vacation packages

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

Monastero di Cortona Hotel & Spa

Cortona Old Town

$1,292

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

A full-service spa and an indoor pool are featured at this luxury hotel. Enjoy the hot tub and free perks like full breakfast and WiFi in public areas. You'll appreciate the sauna, bar/lounge, and snack bar/deli.

Aurum Uffizi

Historic Centre of Florence

$1,581

per person

Dec 26 - Jan 1

found 20 hours ago

Roundtrip non-stop flight included

New York (JFK) 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.

Aurum Firenze

Historic Centre of Florence

$1,497

per person

Dec 26 - Jan 1

found 20 hours ago

Roundtrip non-stop flight included

New York (JFK) 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.

Glance Hotel In Florence

Historic Centre of Florence

$2,087

per person

Nov 21 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This hotel features a bar/lounge, a poolside bar, and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.

Hotel Roma

Historic Centre of Florence

$2,193

per person

Dec 29 - Jan 4

found 1 hour ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Florence (FLR)

This hotel features a gym and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and limo/town car service are also offered.

Top Chianti Region hotels deals

hu Firenze Certosa camping in town

Via San Cristofano 2 Impruneta FI

Free Cancellation

Reserve now, pay when you stay

$42 nightly

$50 total

Oct 21 - Oct 22

Total with taxes and fees

This campground features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop is provided and the front desk is staffed around-the-clock.

Pool

Pet friendly

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

$332 nightly

$376 total

Oct 30 - Oct 31

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.

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$270 total

Oct 26 - Oct 27

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

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$75 total

Nov 1 - Nov 2

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

$78 nightly

$92 total

Nov 6 - Nov 7

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.

Il Borro - Relais & Châteaux

Località Borro, 1 Loro Ciuffenna AR

$483 nightly

$532 total

Nov 2 - Nov 3

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.

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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 $1,292. 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.