Chianti Region Vacation Packages 2026 from $1,283

Chianti Region flight + hotel vacation packages

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

Aurum Uffizi

Historic Centre of Florence

$1,283

per person

Jul 24 - Jul 30

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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 Moon Boutique Hotel & Spa

Historic Centre of Florence

$2,233

per person

Jul 3 - Jul 9

found 1 hour ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

This hotel features a full-service spa and a bar/lounge. WiFi in public areas is free. Self parking, a snack bar/deli, and express check-out are also offered.

Donati Luxury Tower Suites

Historic Centre of Florence

$2,314

per person

Jul 7 - Jul 11

found 1 day ago

Roundtrip non-stop flight included

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

This hotel features free WiFi in public areas, concierge services, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,574

per person

Jul 24 - Jul 30

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

The Sense Experience Resort - Preferred Hotels & Resorts

Save 100% on your flight

$2,487

per person

Jul 21 - Jul 27

found 16 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

A private beach, 3 restaurants, and an outdoor tennis court are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and complimentary bicycles are available on site. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Top Chianti Region hotels deals

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

$63 nightly

$77 total

Jun 4 - Jun 5

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

Relais Vignale & Spa

Via Pianigiani 9 Radda in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$219 total

May 13 - May 14

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the seasonal outdoor pool and perks like 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

$424 nightly

$479 total

Jun 2 - Jun 3

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

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$226 total

Jun 5 - Jun 6

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

Hotel Borgo di Cortefreda Relais

Via Roma 191 Barberino Tavarnelle FI

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$259 total

May 27 - May 28

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 perks like free self parking and free WiFi.

Pool

Spa

Salvadonica - Borgo del Chianti

Via Grevigiana, 82 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$205 total

May 13 - May 14

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

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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.

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 romantic area.

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $1,283. 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.