Castel San Gimignano Vacations from $1,162
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The Latest Castel San Gimignano Vacation Packages
- Aurum Firenze
Sep 28 - Oct 3Aurum Firenze + Flight
Historic Centre of Florence4 nights4.0 star property7.4/10 - Good (1,009 reviews)Roundtrip • New York (EWR) - Florence (FLR)EWR - FLR • 1 stop FLR - EWR • 2 stops$1,610$1,162found 0 hours agoper traveler - The Moon Boutique Hotel & Spa
Oct 19 - Oct 25The Moon Boutique Hotel & Spa + Flight
Historic Centre of Florence5 nights4.0 star property9.6/10 - Exceptional (580 reviews)"Everything was great! Friendly staff, clean and comfortable rooms, and a relaxing atmosphere overall. We really enjoyed our stay!"Reviewed August 1, 2026Roundtrip • New York (EWR) - Florence (FLR)EWR - FLR • 1 stop FLR - EWR • 1 stop$2,721$1,834found 23 hours agoper traveler - The Rif - Boutique Hotel
Oct 5 - Oct 11The Rif - Boutique Hotel + Flight
Pisa City Centre5 nights3.0 star property8.8/10 - Excellent (69 reviews)Roundtrip • New York (JFK) - Florence (FLR)JFK - FLR • 1 stop FLR - JFK • 1 stop - Hotel Duomo Firenze
Oct 19 - Oct 24Hotel Duomo Firenze + Flight
Historic Centre of Florence5 nights3.0 star property9.2/10 - Wonderful (1,003 reviews)"We had a wonderful time celebrating ahead of our wedding at Hotel Duomo! The desk was so warm and welcoming. We truly had an authentic experience."Reviewed August 4, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FCO • Nonstop FCO - EWR • 1 stop$2,094$1,489found 1 day agoper traveler - Villa Cora
Oct 21 - Oct 25Villa Cora + Flight
Oltrarno3 nights5.0 star property9.8/10 - Exceptional (481 reviews)Roundtrip • New York (JFK) - Florence (FLR)JFK - FLR • 1 stop FLR - JFK • 1 stop$2,894$2,064found 1 day agoper traveler
Castel San Gimignano Hotel Deals
Antico Borgo il Cardino
Antico Borgo il Cardino"Super friendly staff, this is a family run b&b & they also have a restaurant in the village an easy 10 minute walk away where the food is fabulous. Breakfast is delivered to your room terrace, you order what you want the night before. The choice is great, eggs, fruit, pastries, yogurt, ham, cheese etc. The rooms are comfortable & clean. The swimming pool and surrounding views are lovely and there are children’s facilities such as swings, slides etc. What makes this place are the staff, all...
Hotel Casolare Le Terre Rosse
Hotel Casolare Le Terre Rosse"This hotel is located in the most beautiful place in Tuscany. My husband and I were very impressed with the tranquility and picturesque beauty we were awed by daily. The staff are very friendly, the food is fabulous and it was just the perfect environment to explore wineries and castles or just lay back having a cocktail and swimming in their pool."
Hotel Pescille by Double Hospitality
Hotel Pescille by Double Hospitality
Hotel Palazzo Renieri - 3stelle S
Hotel Palazzo Renieri - 3stelle S"We never had time for breakfast unfortunately "
"Martina was incredibly kind and helpful throughout our stay. The hotel facilities and breakfast were amazing. The property is located just a few minutes from the town of San Gimignano, making it a perfect base for exploring the area."
"Room was clean, staff was helpful and easy to park."
Frequently Asked Questions
How much does a Castel San Gimignano vacation package cost?
You'll find cheap prices from $1,162 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.