Castel San Gimignano Vacations from $1,088

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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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,656, price is now $1,088 per person
$1,088
per person
Sep 29 - Oct 3
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.

Reviewed on Jul 3, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,977, price is now $1,155 per person
$1,155
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Clean, conveniently located hotel with friendly, helpful staff.

Reviewed on Jul 5, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $1,800, price is now $1,190 per person
$1,190
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (1,002 reviews)
Great stay overall especially in the courtyard

Reviewed on Jul 7, 2026

Hotel Palazzo Ognissanti

Hotel Palazzo Ognissanti

4 out of 5
Historic Centre of Florence
Price was $2,080, price is now $1,413 per person
$1,413
per person
Sep 29 - Oct 3
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.8/10 Good! (493 reviews)
Front of house was friendly, helpful and polite. Showed us where to go, stored our luggage safe and when we came back to check in they had taken cases upstairs for us! Room was basic but clean. Lovely view of Duomo. I was offered a complementory bottle of wine which was red(i only drink white) and they were so accomodating- bringing up a tray eith crisps and ice bucket too. Breakfast was nice, basic bit almost we needed. Closest to the train station, supermarket and fruit and veg shop. Restaurant on same side of road was lovely. Could not have had a better stay. Would totally recommend .

Reviewed on May 21, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $5,300, price is now $3,800 per person
$3,800
per person
Sep 29 - Oct 3
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (315 reviews)
The staff was fantastic. Very helpful. The location is great.

Reviewed on May 4, 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

$159
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
Discover Chianti Through its Wines

Discover Chianti Through its Wines

$51
per adult
Discover Chianti Through its Wines
Small Group Chianti Wineries Tuscan Lunch San Gimignano and more

Small Group Wine Tour & San Gimignano Visit

$217
per adult
100% of travellers recommend
Small Group Wine Tour & San Gimignano Visit
See all activities in Castel San Gimignano

Castel San Gimignano Hotel Deals

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
$448 nightly
The price is $504 total per night from Jul 12 to Jul 13
$504 total
Jul 12 - Jul 13
Total with taxes and fees
9.4/10 Exceptional! (211 reviews)
"Absolutely wonderful stay. The onsite restaurant was amazing and the staff was very attentive and helpful. There are nice wineries and restaurants nearby too and the concierge made very helpful recommendations and reservations for us. Use the hotel name (and not just the address) since the Apple ..."

Reviewed on Jul 8, 2026

Borgo Scopeto Wine & Country Relais
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $162 total per night from Jul 29 to Jul 30
$162 total
Jul 29 - Jul 30
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful rooms, we had one with the terrace and a view. Very quiet. Gorgeous rooftop restaurant, easy parking. 10 min walk to the square."

Reviewed on Jul 9, 2026

Hotel Athena
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $93 total per night from Jul 20 to Jul 21
$93 total
Jul 20 - Jul 21
Total with taxes and fees
8.4/10 Very Good! (543 reviews)
"Nice clean hotel. Breakfast ok. Good parking"

Reviewed on Jul 6, 2026

Hotel Executive
See all 6,457 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 $1,088 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.