Chianti Region Vacation Packages 2025/2026 from $723

Chianti Region flight + hotel vacation packages

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

The Moon Boutique Hotel & Spa

Historic Centre of Florence

Save 100% on your flight

per person

Oct 30 - Nov 4

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

The Sense Experience Resort

per person

Sep 21 - Sep 27

found 19 hours ago

Roundtrip flight included

New York (JFK) 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.

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

per person

Sep 26 - Oct 1

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.

Grand Hotel Cavour

Historic Centre of Florence

Save 100% on your flight

per person

Sep 23 - Sep 29

found 18 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

This hotel features a gym and a rooftop terrace. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.

Palazzo Firenze by Baglioni Hotels & Resorts

Historic Centre of Florence

Save 100% on your flight

per person

Oct 30 - Nov 4

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the free buffet breakfast each morning.

Top Chianti Region hotels deals

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Free Cancellation

Reserve now, pay when you stay

$51 nightly

$63 total

Aug 31 - Sep 1

Total includes 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

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13, Gaiole in Chianti, SI

Free Cancellation

Reserve now, pay when you stay

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

Hotel Borgo di Cortefreda Relais

Via Roma 191, Barberino Tavarnelle, FI

Free Cancellation

Reserve now, pay when you stay

$157 nightly

$180 total

Aug 28 - Aug 29

Total includes taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the children's pool, picnic area, and in-room childcare. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Il Borro - Relais & Châteaux

Località Borro, 1, San Giustino Valdarno, Loro Ciuffenna, AR

$632 nightly

$695 total

Aug 31 - Sep 1

Total includes taxes and fees

An attached winery, 2 restaurants, and 2 outdoor tennis courts are all featured at this Tuscan-style 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

Castello di Fonterutoli Wine Resort

Via Puccini 4, Castellina in Chianti, SI

Free Cancellation

Reserve now, pay when you stay

$191 nightly

$214 total

Aug 23 - Aug 24

Total includes taxes and fees

An attached winery and a restaurant are featured at this smoke-free bed & breakfast. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Limo/town car service, a snack bar/deli, and a library are also on offer.

Pet friendly

Free WiFi

Salvadonica - Borgo del Chianti

Via Grevigiana, 82, San Casciano in Val di Pesa, FI

Free Cancellation

Reserve now, pay when you stay

$276 nightly

$308 total

Aug 25 - Aug 26

Total includes 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

Castello di Meleto, Gaiole in Chianti, Tuscany

Meleto Castle

Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

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 churches and wineries in this walkable area.

The Mall Luxury Outlet

4.5/5(138 reviews)

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

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only $723. 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.