Castel San Gimignano Vacations from $974

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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
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
I’ve had a wonderful stay at Autumn Hotel! It was very clean! The staff was amazing the room was perfect with a balcony you didn’t hear the busy noise from the street at night I will definitely book with them again! Thank you!

Reviewed on Jul 19, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
Everything was perfect! Thank you!!

Reviewed on Jul 20, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 8 - Oct 14
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun 6, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Excellent location right in the middle of everything. If thinking about using public transportation The hotel is on the C bus line these are small electric buses very difficult to get luggage on had to get a taxi

Reviewed on Jul 15, 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

Students and family friendly tours

Tuscany Vespa Tour from Florence with Wine Tasting

$235
per adult
100% of travellers recommend
Tuscany Vespa Tour from Florence with Wine Tasting
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$140
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
San Gimignano: Chianti wine tasting and lunch

San Gimignano: Chianti wine tasting and lunch

$82
per adult
San Gimignano: Chianti wine tasting and lunch
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 refundable
$132 nightly
The price is $151 total per night from Jul 30 to Jul 31
$151 total
Jul 30 - Jul 31
Total includes taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"The front desk that was exceptional"

Reviewed on Jul 18, 2025

Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Aug 20 to Aug 21
$137 total
Aug 20 - Aug 21
Total includes taxes and fees
8/10 Very Good! (993 reviews)
Very nice hotel
"Very nice and clean hotel. Just outside the ztl, close to historic city centre area."

Reviewed on Jul 10, 2025

NH Siena
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $208 total per night from Jul 28 to Jul 29
$208 total
Jul 28 - Jul 29
Total includes taxes and fees
9.2/10 Wonderful! (429 reviews)
"We were a group of 10 who just returned from a 4 night stay at this beautiful hotel. It exceeded our groups expectations. It is quaint, in a beautiful setting. The staff was excellent, accommodating any request that was made. Restaurant is very good, included breakfast was great, many choices. We ..."

Reviewed on Jun 29, 2025

Hotel Borgo di Cortefreda Relais
See all 6,699 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 $974 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.