Chianti Region Vacation Packages 2026 from $1,258

Chianti Region flight + hotel vacation packages

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

Aurum Uffizi

Historic Centre of Florence

$1,258

per person

Jul 8 - Jul 14

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

Precise Tale Poggio Alla Sala

Save 100% on your flight

$2,344

per person

Jul 30 - Aug 5

found 24 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Family-friendly amenities include a playground and in-room childcare. Enjoy the 24-hour gym and free perks like buffet breakfast and WiFi in public areas.

Hotel degli Orafi

Historic Centre of Florence

$1,560

per person

Jul 30 - Aug 5

found 24 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This hotel features a rooftop terrace and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a garden, and a snack bar/deli are also on offer.

Borgo Scopeto Wine & Country Relais

$1,989

per person

Jul 30 - Aug 5

found 24 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the 2 outdoor tennis courts and free perks like buffet breakfast and free self parking.

Aurum Firenze

Historic Centre of Florence

$1,438

per person

Jul 6 - Jul 11

found 6 hours ago

Roundtrip non-stop 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.

Top Chianti Region hotels deals

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$76 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

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$418 nightly

$472 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

Relais Vignale & Spa

Via Pianigiani 9 Radda in Chianti SI

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$227 total

May 26 - May 27

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

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$160 total

May 24 - May 25

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.

Salvadonica - Borgo del Chianti

Via Grevigiana, 82 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$247 nightly

$276 total

Jun 2 - Jun 3

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

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$180 total

May 24 - May 25

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

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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

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 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 $1,258. 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.