Castiglion Fiorentino Vacation Packages

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Your Castiglion Fiorentino Vacation

There's no better way to travel than with one of our vacation packages to Castiglion Fiorentino. The rich history and spectacular views are just two of the convincing reasons to visit this captivating city. If sightseeing is on the agenda during your trip to Castiglion Fiorentino, stop by top attractions like Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona. Whoever you're taking time off with and whatever you want to spend, your ultimate Castiglion Fiorentino vacation is just clicks away with Expedia.

Top Castiglion Fiorentino Vacation Deals

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
London (LON) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
The property is very centrally located—just a short walk from the Duomo and the central train station, with easy access to the tram as well. I was pleasantly surprised by how convenient the location was. The staff were friendly, and the included breakfast was a nice way to start the day with a quick bite. The only suggestion I’d make is to provide a thicker blanket for added comfort.

Reviewed on Jul. 29, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
London (LON) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun. 6, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
London (LON) to Florence (FLR)
No reviews
Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul. 18, 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (117 reviews)
Property is beautiful everywhere you turn, straight out of a movie! Hotel is located at the top of a mountain and you get to over see the vineyards and cities., absolutely beautiful views. The only downside is the hotel only has 2 restaurants that offer diner and they alternate on which night they are opened, you also need reservations in advance and even then tables with a view are not guaranteed.

Reviewed on Jul. 25, 2025

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Castiglion Fiorentino Hotel Deals

Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
9.4/10 Exceptional! (66 reviews)
Family vacation
"Was wonderful and beautiful."

Reviewed on Nov. 30, 2024

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Farmhouse in the hills with panoramic view and swimming pool
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
Fully refundableReserve now, pay when you stay
The price is CA $667 per night from Aug 25 to Aug 26
CA $667
CA $744 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (103 reviews)
"The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the ..."

Reviewed on Jul. 19, 2025

Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $832 per night from Aug 9 to Aug 10
CA $832
CA $928 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (215 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on Jul. 9, 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,816 properties in Castiglion Fiorentino
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.
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What to do in Castiglion Fiorentino

Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

CA $83
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
A Classic Tuscan Winery with Lunch in Montepulciano

A Classic Tuscan Winery with Lunch in Montepulciano

CA $144
per adult
A Classic Tuscan Winery with Lunch in Montepulciano
WELCOME!

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

CA $64
per adult
Private visit to the House of Grand Duke Leopold of Tuscany with invitation
See all activities in Castiglion Fiorentino

Frequently asked questions

How much does a Castiglion Fiorentino vacation package cost?
Offering great value package deals from CA $677 on Expedia, you'll be thrilled with how little a vacation to Castiglion Fiorentino costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Castiglion Fiorentino?
To score cheap Castiglion Fiorentino vacation packages, plan your trip outside of busy periods like public holidays and major festivals. You'll typically find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Castiglion Fiorentino?
With about 3 days, you'll have enough time to experience popular neighbourhoods like Cortona Old Town and Sodo during your Castiglion Fiorentino vacation. Make sure to also add Eremo Le Celle and Belvedere to your sightseeing list. Looking for more adventures? Consider venturing outside of Castiglion Fiorentino on tours and day trips.
Is it worth booking a vacation package to Castiglion Fiorentino?
Whether you're looking to explore top attractions like Cassero Tower and Municipal Art Gallery on your Castiglion Fiorentino vacation, or coming for its excellent nightlife, views and walking trails, there's something for everyone here. With so many things to see and do, you'll soon find out why so many families think Castiglion Fiorentino is a good vacation destination.
How to find the best Castiglion Fiorentino package deals?
Use Expedia's filters to help you find some tempting Castiglion Fiorentino package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Castiglion Fiorentino package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Castiglion Fiorentino vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Castiglion Fiorentino vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Castiglion Fiorentino?
If you're considering a spur-of-the-moment Castiglion Fiorentino vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Castiglion Fiorentino?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Castiglion Fiorentino.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Castiglion Fiorentino.
  3. Decide your trip length: Think about how long you'd like to spend discovering Castiglion Fiorentino. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Castiglion Fiorentino vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.