Castel San Gimignano Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Castel San Gimignano
Price found within the past 48 hours. Click for updated prices.
Grand Hotel Cavour
Historic Centre of Florence
€859
per person
25 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
They were very accommodating and helped with suggestions for places to eat local shops and their breakfast buffet was amazing
Reviewed on 23 Aug 2026
Top hotels in Castel San Gimignano
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
€170
27 Aug - 28 Aug
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"The hotel was close downtown Siena and parking was on site. The continental breakfast was delicious. The room was clean and bed was comfortable. The AC keep shutting off in the night, made it uncomfortable for sleep."
Reviewed on 18 Aug 2026
Castelfalfi
Loc. Castelfalfi Montaione FI
€986
17 Sept - 18 Sept
includes taxes & fees
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
€430
27 Aug - 28 Aug
includes taxes & fees
9.2/10 Wonderful! (624 reviews)
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Reviewed on 18 Aug 2026
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.
What to do in Castel San Gimignano
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
€49
per adult
78% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
€139
per adult
86% of travellers recommend
Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
€35
per adult
Frequently asked questions
How much does a Castel San Gimignano holiday package cost?
You'll find cheap prices from €619 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 holiday to Castel San Gimignano costs.
What are the cheapest months to go to Castel San Gimignano?
The off-season is the best time to visit Castel San Gimignano if you're on a budget. Another tip for scoring cheap Castel San Gimignano holiday packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Castel San Gimignano?
The ideal duration for your Castel San Gimignano holiday depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to hit all the leading sights and discover some hidden treasures along the way.
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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Castel San Gimignano holiday as a package?
You can enjoy significant savings on your next Castel San Gimignano break by booking a customised holiday 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 holiday 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.
How to plan a trip to Castel San Gimignano?
- Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to visit Castel San Gimignano.
- Set your budget: Consider costs like flights, transportation and food when working out how much to put aside for your trip to Castel San Gimignano. Then, select a hotel that works with your budget, whether that's a low-cost stay or a lavish getaway.
- Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Castel San Gimignano. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your accommodation and airfare: Once you've nailed down your travel dates and duration, lock in the perfect Castel 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.
