Castel San Gimignano Vacations from $1,349
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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 Villa Liana
Historic Centre of Florence
$1,349
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (360 reviews)
clean, spacious, well-stocked with toiletries and breakfast items too. walkable distance to all iconic sites. Grace, the breakfast host, did an incredible job, very welcoming & served with options for hot coffee drinks. All together, wonderful, memorable stay!!
Reviewed on May 23, 2026
Dimora Palanca Boutique & SPA
Historic Centre of Florence
$1,830
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (68 reviews)
Lovely hotel, very friendly staff and great location just outside hustle and bustle of Florence.
Reviewed on Apr 21, 2026
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View all tripsWhat to do in Castel San Gimignano
Florence Day Trip: Medieval Villages & Cooking Class
$158
per adult
86% of travellers recommend
Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace
$56
per adult
Castel San Gimignano Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$175 nightly
$199 total
Aug 27 - Aug 28
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"The hotel was close downtown Siena and parking was on site. The continental breakfast was delicious. The room was clean and bed was comfortable. The AC keep shutting off in the night, made it uncomfortable for sleep."
Reviewed on Aug 18, 2026
Castelfalfi
Loc. Castelfalfi Montaione FI
$982 nightly
$1,092 total
Aug 29 - Aug 30
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$403 nightly
$457 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (624 reviews)
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Reviewed on Aug 18, 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 $1,349 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.
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- Visit Lucciana
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- Visit Pignano
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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.
