Castel San Gimignano Vacations from $738

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Villa Olmi Firenze

Villa Olmi Firenze

4 out of 5
Price was $1,043, price is now $738 per person
$738
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (739 reviews)
Beautiful property & amazing staff

Reviewed on Jul 8, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,028, price is now $1,091 per person
$1,091
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,004 reviews)
Very clean, aircon definitely welcome in summer temperatures, breakfast buffet very good. All within walkable distance of the Palazzo Vecchio and other attractions.

Reviewed on Aug 30, 2025

Cala Beach Resort

Cala Beach Resort

5 out of 5
Save 100% on your flight
Price was $3,368, price is now $1,880 per person
$1,880
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (1 review)
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,569, price is now $886 per person
$886
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,008 reviews)
Close to centre of Florence, room ok, clean

Reviewed on Aug 28, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $17,174, price is now $10,463 per person
$10,463
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on Aug 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Castel San Gimignano
View all trips

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
Students and family friendly tours

Tuscany Vespa Tour from Florence with Wine Tasting

$232
per adult
100% of travellers recommend
Tuscany Vespa Tour from Florence with Wine Tasting
San Gimignano: Chianti wine tasting and lunch

San Gimignano: Chianti wine tasting and lunch

$81
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 refundableReserve now, pay when you stay
$207 nightly
The price is $234 total per night from Sep 1 to Sep 2
$234 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"Excellent staff who are always on standby for anything that you need."

Reviewed on Aug 23, 2025

Hotel Athena
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 $66 total per night from Sep 7 to Sep 8
$66 total
Sep 7 - Sep 8
Total with taxes and fees
Hotel Ristorante Alcide
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
$422 nightly
The price is $476 total per night from Sep 8 to Sep 9
$476 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (181 reviews)
"Beautiful property, excellent service"

Reviewed on May 31, 2025

Borgo Scopeto Wine & Country Relais
See all 6,748 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Castel San Gimignano vacation package cost?
You'll find cheap prices from $738 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.