Castel San Gimignano Holidays

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Top Flight + Hotel Deals in Castel San Gimignano

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
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Very small rooms and bathrooms. Breakfast and breakfast staff were awesome and on the top floor. Hotel room small and nothing special. Great location and quiet…but good luck getting out of a car with luggage.

Reviewed on 4 Aug 2025

Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (190 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on 22 Jun 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
per person
9 Sept - 14 Sept
found 13 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (387 reviews)
Great place to stay near Florence, it’s quite and relaxing. The pool is great.

Reviewed on 31 Jul 2025

Villa Olmi Firenze

Villa Olmi Firenze

4 out of 5
per person
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (735 reviews)
Beautiful property & amazing staff

Reviewed on 8 Jul 2025

Rivalta Hotel

Rivalta Hotel

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (361 reviews)
Amazing location!!! Staff are super nice and welcoming.

Reviewed on 2 Aug 2025

Top hotels in Castel San Gimignano

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
The price is €142 per night from 10 Aug to 11 Aug
€142
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"This is a great location if you are driving to Siena. It was close to all the attractions. Great view from our room. Easy to find by car and on foot."

Reviewed on 1 Aug 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
The price is €119 per night from 17 Aug to 18 Aug
€119
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (682 reviews)
"Amazing property with a back patio to die for. Nothing like eating a superb breakfast and enjoying a view of the hills and city."

Reviewed on 2 Aug 2025

Palazzo Ravizza
Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67, Siena, SI
9/10 Wonderful! (982 reviews)
"Our host was incredibly helpful to our itinerary questions. The breakfast was good. The only minor points to note are the presence of mosquitoes and the shared bathroom, but these are the personal preferences"

Reviewed on 2 Aug 2025

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Hotel Italia
See all 6,716 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.

Popular places to visit

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

Medieval Criminal and Torture Museum

This intriguing museum highlights the callousness of humans via displays of authentic and gruesome torture devices from around the world.

Medieval Criminal and Torture Museum

Vernaccia di San Gimignano Wine Museum

You can browse the exhibits at Vernaccia di San Gimignano Wine Museum, a museum with a storied past, during your holiday in San Gimignano. Discover the area's beautiful countryside or seek out its local tours.

Vernaccia di San Gimignano Wine Museum

What to do in Castel San Gimignano

Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

€49
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

€119
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
San Gimignano oil mill experience and oil tasting

San Gimignano oil mill experience and oil tasting

€20
per adult
San Gimignano oil mill experience and oil tasting
See all activities in Castel San Gimignano

Frequently asked questions

How much does a Castel San Gimignano holiday package cost?
You'll find cheap prices from €447 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.