Castelfalfi Vacations from $562

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Your Castelfalfi Vacation

The stress-free way to experience this unique city is with a tailor-made Castelfalfi vacation package. Base yourself in the neighborhood of Capannoli, which is good for walking, nature and history or choose someplace else — our packages are all about you. If visiting the sights is a must during your trip to Castelfalfi, make sure you swing by popular attractions like Castelfalfi Golf Course and Monastery of San Vivaldo. Don't delay your visit to this city any longer. Your perfect Castelfalfi vacation is only a few clicks away with Expedia.

The Latest Castelfalfi vacation packages

Price found within the past 48 hours. Click for updated prices.
Castello di Bossi

Castello di Bossi

2 out of 5
Price was $685, price is now $562 per person
$562
per person
Dec 9 - Dec 13
found 17 hours ago
Roundtrip flight included
Tel Aviv (TLV) to Florence (FLR)
7.8/10 Good! (8 reviews)

The Place Firenze

The Place Firenze

5 out of 5
Historic Centre of Florence
Price was $2,138, price is now $1,616 per person
$1,616
per person
Dec 9 - Dec 13
found 5 hours ago
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.8/10 Exceptional! (203 reviews)

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $1,075, price is now $860 per person
$860
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.2/10 Wonderful! (78 reviews)
All

Reviewed on Oct 31, 2026

The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was $1,067, price is now $853 per person
$853
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Very nice staff, clean rooms and great room service and nice furniture ! Close to the main touristy places in the city, maximum of 30 minutes walk radius from everything that I wanted to visit!

Reviewed on Nov 2, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was $1,476, price is now $1,198 per person
$1,198
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.8/10 Exceptional! (82 reviews)
Great location. Historical building. Rooms were stunning. Lovely breakfast box delivered daily. Nice staff. The only negative is the roof is €250 per 2 hour booking, which I didn't expect, and would have been a reason for booking. Hence 4/5.

Reviewed on Oct 19, 2026

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Stay near popular Castelfalfi attractions

Castelfalfi Golf Course

9.6/10 (11 reviews)
Enjoy a round of golf in Castelfalfi at Castelfalfi Golf Course. Discover the beautiful countryside in this relaxing area.
See properties

What to do in Castelfalfi

San Gimignano: Evening Flavors Dinner & Wine tasting

San Gimignano: Evening Flavors Dinner & Wine tasting

$63
per adult
San Gimignano: Evening Flavors Dinner & Wine tasting
Frantoio di San Gimignano: tour of the oil mill and tasting

Frantoio di San Gimignano: tour of the oil mill and tasting

$22
per adult
Frantoio di San Gimignano: tour of the oil mill and tasting
Private Wine & Oil Tasting with Lunch

Private Wine & Oil Tasting with Lunch

$76
per adult
Private Wine & Oil Tasting with Lunch
See all activities in Castelfalfi

Castelfalfi Hotel Deals

Castelfalfi

Castelfalfi

5 out of 5
Località Castelfalfi Montaione FI
$823 nightly
The price is $916 total per night from Nov 8 to Nov 9
$916 total
Nov 8 - Nov 9
Total with taxes and fees
9.6/10 Exceptional! (190 reviews)
"Get ready to be impressed if you stay here. Every staff member from our arrival to our departure genuinely greeted us and welcomed us and many remembered our name. They always asked if we needed anything or offered help or suggestions in a genuine “we want to help way”. The concierge before our stay ..."

Reviewed on Oct 29, 2026

Castelfalfi
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Nov 26 to Nov 27
$124 total
Nov 26 - Nov 27
Total with taxes and fees
Poderi Arcangelo
Villa Petriolo

Villa Petriolo

Via di Petriolo 7 Cerreto Guidi FI
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $245 total per night from Dec 4 to Dec 5
$245 total
Dec 4 - Dec 5
Total with taxes and fees
Villa Petriolo
See all 6,233 properties in Castelfalfi
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.

Find the Best Castelfalfi Vacation Packages

Castelfalfi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)
Top Sights
Castelfalfi Golf Course, Monastery of San Vivaldo and Villa da Filicaja

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Frequently asked questions

How much does a Castelfalfi vacation package cost?
Offering excellent value package deals from $562 on Expedia, you'll be thrilled with how little a vacation to Castelfalfi costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Castelfalfi?
You can typically find lower rates and greater availability in October, November and December. Check out our cheap Castelfalfi vacation packages and you could land some great off-season deals.
How many days is enough for Castelfalfi?
The ideal duration for your Castelfalfi vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to hit all the top sights and explore some hidden gems along the way.
How to find the best Castelfalfi package deals?
Begin your search for a Castelfalfi package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Castelfalfi package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Castelfalfi getaway off to a flying start.
Is it cheaper to book a Castelfalfi vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Castelfalfi escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Castelfalfi?
If you're planning a spontaneous Castelfalfi getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Castelfalfi?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Castelfalfi.
  2. Set your budget: Factor in costs such as food, flights and transportation when working out how much to put aside for your trip to Castelfalfi. Then, choose a hotel that matches your budget, whether that's a low-cost stay or a lavish getaway.
  3. Use our trip planning tool to explore Castelfalfi: Research every part of your trip to Castelfalfi with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how long to go for: Now that you know more about Castelfalfi, you can work out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Castelfalfi vacation package.
  6. Book experiences or activities in advance: Whether it's a ticket to a major attraction or a day trip in nature, you won't have to worry about missing out on the highlights of Castelfalfi. Find all the exciting things to do in Castelfalfi with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Castelfalfi vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Castelfalfi vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.