Castel San Gimignano Vacations from $559

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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 $847, price is now $559 per person
$559
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
Breakfast was excellent

Reviewed on Sep 29, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $955, price is now $599 per person
$599
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Basic , clean and nice staff

Reviewed on Oct 10, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,577, price is now $1,835 per person
$1,835
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Park Palace

Park Palace

4 out of 5
Oltrarno
Price was $926, price is now $669 per person
$669
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9/10 Wonderful! (356 reviews)
Stayed here for four nights with my husband and it was amazing! The breakfast in the morning was delicious and the staff was so friendly and helpful. We loved that it was outside of the busyness of the city but close enough to have a taxi take us back and forth throughout the day. We had the hotel call us a taxi multiple times but also downloaded AppTaxi to get rides back to the hotel which was very convenient. The room was very comfortable and the pool area very peaceful - we loved coming here to wind down after exploring all day! I could not recommend this hotel more!!!

Reviewed on Oct 4, 2025

Palazzo Lorenzo Hotel Boutique & Spa

Palazzo Lorenzo Hotel Boutique & Spa

4 out of 5
San Lorenzo
Price was $1,079, price is now $811 per person
$811
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (585 reviews)
Beautiful hotel, clean room beautifully decorated and with everything needed to make our stay feel luxurious and comfortable. Friendly helpful staff. Delicious buffet breakfast and free use of spa facilities. It felt 5 star!

Reviewed on Sep 27, 2025

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Discover the most popular places to visit in Castel San Gimignano

San Gimignano Communal Palace

San Gimignano Communal Palace

You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

San Gimignano Communal Palace
Piazza Duomo showing a church or cathedral and heritage architecture

Piazza Duomo

Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.

Piazza Duomo
Piazza della Cisterna which includes a city, street scenes and a square or plaza

Piazza della Cisterna

Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.

Piazza della Cisterna

What to do in Castel San Gimignano

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$138
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$57
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Castel San Gimignano

Castel San Gimignano Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Nov 11 to Nov 12
$102 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (999 reviews)
"NA"

Reviewed on Sep 28, 2025

Hotel Athena
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
$50 nightly
The price is $56 total per night from Nov 9 to Nov 10
$56 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (454 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on Jul 7, 2025

Hotel Ristorante Alcide
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Nov 5 to Nov 6
$112 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (723 reviews)
"What a unique and wonderful experience! This hotel is situated in the walled city and they helped us navigate in and out of the limited traffic zone. They also made a reservation for us at the most amazing little restaurant in Siena and just treated us spectacularly! Thank you for taking care of ..."

Reviewed on Oct 6, 2025

Palazzo Ravizza
See all 6,670 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.

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 $559 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.