Castiglioncello del Trinoro Vacations from $704

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Your Castiglioncello del Trinoro Vacation

From its highlights to its hidden gems, this city is best experienced with a Castiglioncello del Trinoro vacation package. Look for places to stay in Villastrada, which is good for festivals, culture and nature. Eager to do some sightseeing? A trip to Castiglioncello del Trinoro wouldn't be complete without exploring Sarteano Castle, Archaeological Museum of Sarteano and other big-name attractions. No matter your travel plans or the size of your budget, organizing a tailored Castiglioncello del Trinoro vacation is easy with Expedia.

The Latest Castiglioncello del Trinoro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,200, price is now $704 per person
$704
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (470 reviews)
Hotel was clean and nice. The staff was genuinely very welcoming, helpful and hospitable. Breakfast was delicious everyday.

Reviewed on Sep 3, 2025

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Save 100% on your flight
Price was $4,723, price is now $2,898 per person
$2,898
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (220 reviews)
The best hotel we’ve ever stayed in

Reviewed on Sep 2, 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,297 per person
$1,297
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (132 reviews)
This is a lovely hotel. The rooms in the village are fresh and clean. The walk to the hotel was pleasant and looking at the views are stunning. The staff are all professional and curtious. A special thanks to Auri for always smiling. Most important question' would I recommend this hotel, Definitely !

Reviewed on Aug 21, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was $2,372, price is now $1,659 per person
$1,659
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (230 reviews)
Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect

Reviewed on Aug 7, 2025

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Save 100% on your flight
Price was $2,627, price is now $1,876 per person
$1,876
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (182 reviews)
This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint

Reviewed on Sep 2, 2025

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Discover the most popular places to visit in Castiglioncello del Trinoro

Sarteano Castle

Sarteano Castle is just one of the places to see in Sarteano, so why not enjoy the other things to explore during your travels? Visit the area's spas, or simply enjoy its wineries.

Sarteano Castle

Archaeological Museum of Sarteano

You can spend an afternoon browsing the exhibits at Archaeological Museum of Sarteano during your travels in Sarteano. Discover the area's countryside and wineries.

Archaeological Museum of Sarteano

What to do in Castiglioncello del Trinoro

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

$104
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal

Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal

$116
per adult
100% of travellers recommend
Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
See all activities in Castiglioncello del Trinoro

Castiglioncello del Trinoro Hotel Deals

Monteverdi Tuscany

Monteverdi Tuscany

Via di Mezzo, 2 Castiglioncello del Trinoro, Sarteano, SI
Fully refundableReserve now, pay when you stay
$981 nightly
The price is $1,083 total per night from Sep 23 to Sep 24
$1,083 total
Sep 23 - Sep 24
Total with taxes and fees
Monteverdi Tuscany
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $119 total per night from Sep 8 to Sep 9
$119 total
Sep 8 - Sep 9
Total with taxes and fees
Hotel Relais II Chiostro di Pienza
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
$401 nightly
The price is $448 total per night from Oct 4 to Oct 5
$448 total
Oct 4 - Oct 5
Total with taxes and fees
Precise Tale Poggio Alla Sala
See all 3,678 properties in Castiglioncello del Trinoro
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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Frequently asked questions

How much does a Castiglioncello del Trinoro vacation package cost?
Offering great value package deals from $704 on Expedia, you'll be pleasantly surprised at how much a vacation to Castiglioncello del Trinoro costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Castiglioncello del Trinoro?
August, November and December are the best times to search for cheap Castiglioncello del Trinoro vacation packages. Choosing to travel in quieter months means you can usually find lower prices on flights and hotels.
How many days is enough for Castiglioncello del Trinoro?
Typically, a handful of days is enough to check out the major attractions during your Castiglioncello del Trinoro vacation. However, if you want to have time to unwind or take day trips, consider extending your itinerary.
How to find the best Castiglioncello del Trinoro package deals?
Begin your search for a Castiglioncello del Trinoro package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Castiglioncello del Trinoro package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Castiglioncello del Trinoro escape underway.
Is it cheaper to book a Castiglioncello del Trinoro vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Castiglioncello del Trinoro vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Castiglioncello del Trinoro?
If you've got your Castiglioncello del Trinoro vacation dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Castiglioncello del Trinoro vacation packages?
If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Castiglioncello del Trinoro break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.