San Gimignano Holidays

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San Gimignano Holiday

Our pick of the best San Gimignano Hotel Deals

RELAIS SANTA CHIARA - TUSCANY CHARME

RELAIS SANTA CHIARA - TUSCANY CHARME

4 out of 5
Via Giacomo Matteotti, 15, San Gimignano, SI
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (383 reviews)
"We loved our stay. The hotel had really nice breakfasts included and the pool was fantastic after a hot day walking around the old city. We had a standard room and we were expecting it to be small. It was very small - it was difficult to find space for our cases and the shower was so small that it ..."

Reviewed on 20 Jul. 2025

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RELAIS SANTA CHIARA - TUSCANY CHARME
Villasanpaolo

Villasanpaolo

4 out of 5
Strada Provinciale Per Certaldo, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is NZ$410 per night from 24 Aug to 25 Aug
NZ$410
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (215 reviews)
"Very nice hotel. Hope to stay there again."

Reviewed on 13 Jun. 2025

Villasanpaolo
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano, San Gimignano, SI
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (302 reviews)
"Exceptional views from this property. The room was for 4. It had a rustic farm house vibe. Unfortunately there was mold in the bathroom and a nest of spiders in the beams above the bed (which my husband was happy to sleep under - so we ignored). There is no noise insulation between floors and you ..."

Reviewed on 20 Jul. 2025

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Poderi Arcangelo
See all 580 properties in 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.

Discover the most popular places to visit in San Gimignano

Tenuta Torciano Winery

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this relaxing area.

Tenuta Torciano Winery

Torre Grossa

You can find out about the history of San Gimignano with a trip to Torre Grossa. Discover the area's beautiful countryside and wineries.

Torre Grossa

What to do in San Gimignano

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

NZ$232
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
view from the terrace

Cesani Wine Experience

NZ$59
per adult
Cesani Wine Experience
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

NZ$96
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in San Gimignano

Frequently asked questions

How much does a San Gimignano holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to San Gimignano costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to San Gimignano?
If you're hoping to book a cheap San Gimignano holiday package, consider visiting in December, January and February. You'll generally find better rates on hotels and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for San Gimignano?
To get the most out of your San Gimignano holiday, we recommend staying for 3 days. Divide your time between visiting Museo Civico, Museum San Gimignano 1300 and other must-see attractions, as well as experiencing neighbourhoods like San Gimignano City Centre and Bibbiano. If you've got some time to spare, include a day trip or tour in your San Gimignano holiday itinerary.
Is it worth booking a holiday package to San Gimignano?
Whether you're looking to check out major attractions such as Piazza Duomo and Collegiate Church of Santa Maria Assunta on your San Gimignano holiday, or coming for its great nature, views and walking trails, there's something for everyone here. With so many things to see and do, you'll soon learn why so many families think San Gimignano is a good holiday destination.
How to find the best San Gimignano package deals?
Bagging a cheap San Gimignano package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can customise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly San Gimignano package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a San Gimignano holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking stays and flights separately. Better still, you can personalise your San Gimignano trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to San Gimignano?
If you've got your San Gimignano holiday dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to San Gimignano?

  1. Pick your dates: What you'd like to do in San Gimignano and your preferred season will help you decide when to get away.
  2. Budget wisely: On top of the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to San Gimignano.
  3. Decide your trip length: Consider how much time you want to spend exploring San Gimignano. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right San Gimignano holiday package for you.

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