Chianti Region Vacation Packages 2026 from $1,102

Chianti Region flight + hotel vacation packages

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

Maxim Axial

Historic Centre of Florence

$1,102

per person

Apr 15 - Apr 21

just found

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

A bar/lounge and a terrace are featured at this hotel, along with valet parking. WiFi in public areas is free. A garden, luggage storage, and concierge services are also on offer.

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

$1,486

per person

May 12 - May 18

found 1 day ago

Roundtrip non-stop 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.

Aurum Firenze

Historic Centre of Florence

$1,388

per person

May 21 - May 26

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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

Save 100% on your flight

$1,418

per person

May 12 - May 18

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 La Scaletta Al Ponte Vecchio

Historic Centre of Florence

Save 100% on your flight

$2,213

per person

May 21 - May 26

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Top Chianti Region hotels deals

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$49 nightly

$61 total

Mar 15 - Mar 16

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.

Pet friendly

Free WiFi

Borgo Vescine

Località Vescine Radda in Chianti SI

$455 nightly

$510 total

Apr 2 - Apr 3

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

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI

Get rates

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 full breakfast and free self parking.

Pool

Breakfast included

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Get rates

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

Il Borro - Relais & Châteaux

Località Borro, 1 Loro Ciuffenna AR

Free Cancellation

Reserve now, pay when you stay

$522 nightly

$575 total

Mar 12 - Mar 13

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.

Pool

Spa

Salvadonica - Borgo del Chianti

Via Grevigiana, 82 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$112 total

Mar 10 - Mar 11

Total with taxes and fees

An attached winery and an outdoor pool are featured at this smoke-free farm stay. Families will appreciate the bowling alley, onsite laundry facilities, and in-room childcare. Enjoy a meal from the restaurant and perks like free full breakfast and free self parking.

Pool

Breakfast included

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

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

5/5(1 review)

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

4.5/5(138 reviews)

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

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.

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $1,102. 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.