Castel San Gimignano Vacations from $952
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Your Castel San Gimignano Vacation
With everything organized before you head off, our Castel San Gimignano vacation packages mean you can simply focus on enjoying your getaway. Whether you're staying in the neighborhood of Montegabbro, which is great for history, or someplace else, this lively city offers a wealth of discoveries. Make your trip to Castel San Gimignano even more fulfilling by including some sightseeing. Collegiate Church of Santa Maria Assunta, Piazza Duomo and Medieval Criminal and Torture Museum are some of the top attractions worth exploring. A few quick clicks is all it takes to put together your perfect Castel San Gimignano vacation on Expedia.
The Latest Castel San Gimignano vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$952
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
I would say this is a 3.5 star property. The room was clean but basic, same for the bathroom and amenities like soap etc. the location is very central but the room was still quiet. There is no concierge and the staff was not able to make any reservations for us.
Reviewed on Sep 19, 2026
Eurostars Florence Boutique
Historic Centre of Florence
$1,462
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (500 reviews)
mattresses were impossible to sleep on
Reviewed on Sep 14, 2026
Grand Hotel Cavour
Historic Centre of Florence
$2,465
per person
Nov 4 - Nov 9
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !
Reviewed on Sep 15, 2026
Aurum Firenze
Historic Centre of Florence
$1,035
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Brilliant location, no more than 15-20 maximum minutes to walk to all the main sites. The staff worked hard and were very friendly and helpful.
Reviewed on Sep 17, 2026
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See all available trips from Columbus to Castel San Gimignano
View all tripsWhat to do in Castel San Gimignano
Florence Day Trip: Medieval Villages & Cooking Class
$185
per adult
86% of travellers recommend
Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace
$40
per adult
Castel San Gimignano Hotel Deals
Castelfalfi
Loc. Castelfalfi Montaione FI
$807 nightly
$899 total
Oct 18 - Oct 19
Total with taxes and fees
9.6/10 Exceptional! (184 reviews)
"Our stay was perfect. We were given an upgrade due to the fact that it was our honeymoon. The staff was very kind and they work hard at pampering all guests. Property and rooms are extremely clean. Not sure if we went at a good time but the hotel was not crowded at all. Easy access to spa and other ..."
Reviewed on Sep 17, 2026
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$235 nightly
$264 total
Oct 20 - Oct 21
Total with taxes and fees
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
$91 nightly
$110 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (564 reviews)
"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"
Reviewed on Sep 16, 2026
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.
Find the Best Castel San Gimignano Vacation Packages
Castel San Gimignano Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Peretola Airport (FLR) |
Population | 150 |
Max Temp Winter | 50ºF |
Max Temp Summer | 85ºF |
Top Sights | Tenuta Torciano Winery, Sovestro in Poggio Winery and Museo Civico |
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Frequently asked questions
How much does a Castel San Gimignano vacation package cost?
You'll find cheap prices from $952 on Expedia for your Castel San Gimignano getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Castel San Gimignano costs.
What are the cheapest months to go to Castel San Gimignano?
November, December and January are great times to look for cheap Castel San Gimignano vacation packages. Traveling in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Castel San Gimignano?
Generally, a handful of days is enough to see the main attractions during your Castel San Gimignano vacation. But if you want to have some time to kick back or take day tours, think about extending your itinerary.
How to find the best Castel San Gimignano package deals?
Finding a cheap Castel San Gimignano package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Castel San Gimignano package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Castel San Gimignano vacation as a package?
You can enjoy significant savings on your next Castel San Gimignano break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Castel San Gimignano?
If you're planning a spur-of-the-moment Castel San Gimignano adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Castel San Gimignano vacation packages?
Secure your perfect trip to Castel San Gimignano with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stick to your budget and snap up cheap deals while they last.
Explore a world of travel with Expedia
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- Tenuta Torciano Winery
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- Visit Lucciana
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- Archeodromo di Poggibonsi
- Piazza delle Erbe
- Museum of Sacred Art
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- Sant'agostino Church
- Medieval Criminal and Torture Museum
- Ornithological Museum
- Volterra Vacations
- Visit Pignano
- Fonti Medievali
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- Torre Rognosa
- Piazza Luigi Pecori
- Torre Grossa
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- Piazza Duomo
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
