Castiglion Fiorentino Vacation Packages 2025/2026 from $712

Castiglion Fiorentino flight + hotel vacation packages

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

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

$712

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) 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.

Villa Cora

Oltrarno

Save 100% on your flight

$1,219

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking and a free area shuttle.

The Moon Boutique Hotel & Spa

Historic Centre of Florence

Save 100% on your flight

$877

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) 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.

Collegio alla Querce - Auberge Collection

Le Cure

Save 100% on your flight

$1,878

per person

Nov 22 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

A full-service spa, 2 restaurants, and A 24-hour gym are all featured at this luxury hotel. Enjoy the seasonal outdoor pool and perks like free WiFi and a free area shuttle. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

Dimora Palanca Boutique & SPA

Historic Centre of Florence

Save 100% on your flight

$1,038

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

This smoke-free hotel features a full-service spa and a restaurant. Business travelers can take advantage of the free WiFi in public areas. You'll appreciate the in-room fitness, bar/lounge, and snack bar/deli.

Top Castiglion Fiorentino hotels deals

Farmhouse in the hills with panoramic view and swimming pool

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This vacation home features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

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

Hotel Panoramic

Via di Villa Bianca, 8, Montepulciano, SI

$101 nightly

$116 total

Oct 10 - Oct 11

Total with taxes and fees

This hotel features a seasonal outdoor pool and a rooftop terrace. Families will appreciate the playground and picnic area. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.

Pool

Pet friendly

Monastero di Cortona Hotel & Spa

Via del Salvatore, Cortona, AR

Free Cancellation

Reserve now, pay when you stay

$372 nightly

$419 total

Oct 19 - Oct 20

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

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6, Cortona, AR

Free Cancellation

Reserve now, pay when you stay

$504 nightly

$564 total

Oct 11 - Oct 12

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

Precise Tale Poggio Alla Sala

Via Poggio alla Sala 10, Montepulciano, SI

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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

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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

Tennis Club Castiglionese

You can take time to visit Tennis Club Castiglionese during your travels 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.

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.

Frequently asked questions

How much are vacation packages to Castiglion Fiorentino?

$712 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.