Castel San Gimignano Vacations from $1,030

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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 Certosa Di Maggiano

Hotel Certosa Di Maggiano

4 out of 5
Price was $1,417, price is now $1,030 per person
$1,030
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.8/10 Exceptional! (177 reviews)
The property and staff were amazing. The guests were treated to great music and food. We can't wait to go back!

Reviewed on Oct 2, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,136, price is now $1,491 per person
$1,491
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
Very small room and shower without door.not even place to put a chair

Reviewed on Oct 16, 2025

Hotel Ginori al DUOMO

Hotel Ginori al DUOMO

4 out of 5
Historic Centre of Florence
Price was $6,353, price is now $4,510 per person
$4,510
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
New York (LGA) to Florence (FLR)
9/10 Wonderful! (12 reviews)
Excellent hotel with excellent staff. Perfect location

Reviewed on Oct 10, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,371, price is now $1,708 per person
$1,708
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
This is a beautiful hotel.It is spotlessly clean.The staff are friendly and helpful. Breakfast exceeded our expectations. The choice of food and service were excellent. It’s a good location to see the sights and get to the train station to visit Pissa etc. We will definitely book here for our next visit.

Reviewed on Oct 11, 2025

Hotel Continentale - Lungarno Collection

Hotel Continentale - Lungarno Collection

4 out of 5
Historic Centre of Florence
Price was $1,555, price is now $1,148 per person
$1,148
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (709 reviews)
Outstanding boutique hotel and staff. Modern beautiful rooms. Staff went far out of their way to accommodate every request.

Reviewed on Sep 13, 2025

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Discover the most popular places to visit in Castel San Gimignano

San Gimignano Communal Palace

San Gimignano Communal Palace

3/5(1 review)

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

4.5/5(53 reviews)

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

4.5/5(52 reviews)

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
$96 nightly
The price is $110 total per night from Nov 12 to Nov 13
$110 total
Nov 12 - Nov 13
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"We loved that the hotel was on the edge of Siena, but just inside the city wall, so that we could drive right up to the hotel and park but then walk easily anywhere in the city. The hotel itself was lovely, with fantastic staff and excellent breakfast. Our room was clean, very comfortable, with nice ..."

Reviewed on Oct 16, 2025

Hotel Athena
Hotel Pescille - Tuscany Charme

Hotel Pescille - Tuscany Charme

3 out of 5
Strada Statale 47, Localita Pescille, San Gimignano, SI
$100 nightly
The price is $118 total per night from Oct 26 to Oct 27
$118 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (327 reviews)
"Beautiful views!!!"

Reviewed on Sep 24, 2025

Hotel Pescille - Tuscany Charme
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $113 total per night from Nov 5 to Nov 6
$113 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (729 reviews)
"We enjoyed our stay here."

Reviewed on Oct 18, 2025

Palazzo Ravizza
See all 6,560 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 $1,030 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.