Castel San Gimignano Vacations from $996

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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

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
$996
per person
Nov 3 - Nov 8
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
Aurum Firenze

Aurum Firenze

Historic Centre of Florence
$1,191
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
N/a

Reviewed on Sep 13, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

Historic Centre of Florence
$1,200
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (500 reviews)
mattresses were impossible to sleep on

Reviewed on Sep 14, 2026

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

$1,923
per person
Nov 6 - Nov 11
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9/10 Wonderful! (367 reviews)
Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!

Reviewed on Sep 9, 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence
$2,086
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (161 reviews)
Great location!! Gorgeous room, clean, and they were very helpful. I would absolutely stay there again!

Reviewed on Sep 13, 2026

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What to do in Castel San Gimignano

Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$185
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
Tootbus Tuscany Intercity Multi-day Pass

Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace

$40
per adult
Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace
Discover Chianti Through its Wines

Discover Chianti Through its Wines

$52
per adult
Discover Chianti Through its Wines
See all activities in Castel San Gimignano

Castel San Gimignano Hotel Deals

Castelfalfi

Castelfalfi

Loc. Castelfalfi Montaione FI
$952 nightly
$1,058 total
Oct 13 - Oct 14
Total with taxes and fees
9.6/10 Exceptional! (183 reviews)
"Stunning estate. Excellent food."

Reviewed on Sep 9, 2026

Castelfalfi
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$261 nightly
$293 total
Oct 15 - Oct 16
Total with taxes and fees
9.4/10 Exceptional! (1,001 reviews)
"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing ..."

Reviewed on Sep 11, 2026

Hotel Athena
La Certosa di Pontignano

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
$116 nightly
$137 total
Oct 15 - Oct 16
Total with taxes and fees
9.4/10 Exceptional! (561 reviews)
"Beautiful place, very quiet, in love with gardens"

Reviewed on Aug 31, 2026

La Certosa di Pontignano
See all 6,352 properties in Castel San Gimignano
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 $996 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.