Castiglion Fiorentino Vacation Packages 2026 from $1,705

Castiglion Fiorentino flight + hotel vacation packages

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

Hotel Bencista

$1,705

per person

Jun 26 - Jul 2

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) 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 a garden are also on offer.

Residenza Florentia

Historic Centre of Florence

$1,854

per person

May 25 - May 31

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

This hotel features a bar/lounge, free WiFi in public areas, and express check-out. Luggage storage, concierge services, and a virtual front desk are also on offer.

Eurostars Florence Boutique

Historic Centre of Florence

$1,853

per person

May 25 - May 31

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) 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.

Roccamare Resort - Hotel Casa di Ponente

$2,446

per person

Jun 26 - Jul 2

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

A private beach, 2 restaurants, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a free kid's club and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and free self parking.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$3,164

per person

Jun 5 - Jun 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 Castiglion Fiorentino hotels deals

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino

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An outdoor pool is featured at this villa, along with a terrace and a garden. A library, laundry facilities, and barbecue grills are also on offer.

Pool

Kitchen

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

$631 nightly

$704 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and airport shuttle. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26 Pienza SI

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This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Pool

Breakfast included

Precise Tale Poggio Alla Sala

Via Poggio alla Sala 10 Montepulciano SI

Free Cancellation

Reserve now, pay when you stay

$394 nightly

$441 total

May 3 - May 4

Total with taxes and fees

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.

Pool

Breakfast included

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Free Cancellation

Reserve now, pay when you stay

$329 nightly

$371 total

Apr 26 - Apr 27

Total with taxes and fees

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.

Pool

Hot Tub

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI

$283 nightly

$316 total

May 14 - May 15

Total with taxes and fees

An attached winery and an outdoor pool are featured at this smoke-free country house. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.

Pool

Parking 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

Cassero Tower

Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Agricola Buccelletti Winery

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

Frequently asked questions

How much are vacation packages to Castiglion Fiorentino?

$1,705 is all you'll need for a wonderful escape in Castiglion Fiorentino. Bundle your hotel and flights into a vacation package with Travelocity and see your savings add up. With these kinds of prices, you'll want to start packing your bags now!

How long should my Castiglion Fiorentino vacation be?

Many people choose to spend around 2 nights in Castiglion Fiorentino, but it's your choice. If you're hoping to explore all the incredible things this location has to offer, why not hang around another few nights?

Where can I get the best vacation package deals for Castiglion Fiorentino?

It's hard to beat Travelocity when it comes to finding your Castiglion Fiorentino package deal. There are as many as 400 airlines and 1,000,000 worldwide properties to select from. Secure your trip now and get ready to cross another exciting destination off your list.

Why should I book my Castiglion Fiorentino vacation package via Travelocity?

Fantastic savings, an abundance of breathtaking destinations and a team of customer service experts available 24/7 — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.

Can I save money on my Castiglion Fiorentino car rental if I bundle it with hotels and flights?

With a Castiglion Fiorentino vacation package, you can bundle your car, hotel and flight bookings and save tons. If you'd love to uncover the best of this fantastic area, why not make tracks to St. Peter's Basilica? This renowned sight is 100 mi from Castiglion Fiorentino. With your own rental car, you'll be there soon enough.

Which airport is best for Castiglion Fiorentino?

Peretola Airport (FLR), 50 mi northwest of the city center, is where many visitors start their adventures in Castiglion Fiorentino. But it's possible that Federico Fellini Intl. Airport (RMI) (60 mi away from central Castiglion Fiorentino) could be a handier option for you.

What is there to do in Castiglion Fiorentino?

You'll feel an undeniable magic as you stroll the streets of Castiglion Fiorentino. Vasari Loggia and Tennis Club Castiglionese are just a couple of famous sights that make this city so popular, so put them at the top of your to-do list.

Where should I stay when visiting Castiglion Fiorentino?

Many people opt to spend their nights at the Charming and inviting vacation home with communal pool.. It's the perfect base for your Castiglion Fiorentino vacation.