Castel San Gimignano Vacations from $1,057

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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.
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $1,474, price is now $1,057 per person
$1,057
per person
Apr 16 - Apr 20
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (476 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Casual Rinascimento Firenze Hotel

Casual Rinascimento Firenze Hotel

3 out of 5
Historic Centre of Florence
Price was $1,712, price is now $1,117 per person
$1,117
per person
Apr 13 - Apr 15
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.2/10 Wonderful! (268 reviews)
We did not have the breakfast, so no comment to make. The pool was really nice. Our room was immaculate and very spacious. The location was so close to everything nearby we wanted to see. Maybe a small gripe: WiFi showed 2 to 3 bars, but seemed to disconnect for our devices. Still, this was minor and figured it was related to the soundproof like stone walls. Certainly, not a reason to complain to staff or deduct from the overall review. We would 100% choose to stay here again. Thanks

Reviewed on Jan 10, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,699, price is now $1,130 per person
$1,130
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
This is not a typical hotel where there is a lobby or staff to greet you . Instead it is a set of apartments in a corner building . The person who let us in was awaiting for us at the door at check in. Breakfast was serve in a buffet style . Staff would ask if you would order something else if you like. Continental breakfast is available .Overall it was comfortable and easy to find . Shops and restaurants are all walking distance.

Reviewed on Jan 15, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,629, price is now $1,103 per person
$1,103
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
9 day stay. The property hit my must-haves! Central location, clean, affordable, and safe. 5/5 in all these areas! There is nothing they can do about dirty streets but the filth did not cross the threshold. T2 tram from the airport is 2 blocks away. The central market is 2 blocks in the other direction. Key card swipe after dark. 24 hour desk service. Breakfast on the 5th floor with views. Very courteous staff. The only complaint is breakfast tables are cleared very quickly while I went for a americano refill. Will definitely return here.

Reviewed on Jan 3, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,489, price is now $2,467 per person
$2,467
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (299 reviews)
Great location and got fantastic service from the hotel. Room was very clean and comfortable. Definitely my first choice for staying in Firenze!

Reviewed on Nov 17, 2025

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Discover the most popular places to visit in Castel San Gimignano

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
landscapes of Italy. medieval San Gimignano - Tuscany, Shutterstock ID 383524231, SF SSA Case with Manager Approval: Case 07151371, Job: Prepay credit, Client/Licensee: , Other:

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

What to do in Castel San Gimignano

Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$48
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$162
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
The Winery view

Discover Chianti Through its Wines

$49
per adult
Discover Chianti Through its Wines
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
$94 nightly
The price is $107 total per night from Feb 22 to Feb 23
$107 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
It’s very beautiful

Reviewed on Jan 9, 2026

Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$280 nightly
The price is $315 total per night from Feb 23 to Feb 24
$315 total
Feb 23 - Feb 24
Total with taxes and fees
9.2/10 Wonderful! (577 reviews)
Staff is amazing! The hotel is beautiful! Hotel is very clean and a respite from walking all day! Be sure and ask for different pillows if you are particular... they have many kinds to choose from!

Reviewed on Jan 20, 2026

Grand Hotel Continental Siena – Starhotels Collezione
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A Poggibonsi SI
Fully refundableReserve now, pay when you stay
$53 nightly
The price is $58 total per night from Feb 15 to Feb 16
$58 total
Feb 15 - Feb 16
Total with taxes and fees
8/10 Very Good! (462 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
See all 6,158 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 $1,057 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.