Castelfalfi Vacations from $1,310

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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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,867, price is now $1,310 per person
$1,310
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
The location is perfect, you can see the stunning view from the breakfast area. But if the breakfast items can be more choice. Shower room a bit small

Reviewed on May 9, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $4,196, price is now $2,765 per person
$2,765
per person
Jun 19 - Jun 23
found 12 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (61 reviews)
Fabulous old building but fully refurbished with modern suites. Only 12 suites, all unique with 2 on each floor. Loads of room. Staff fabulous. Only minus point is there’s no bar or restaurant, but it is located within an area that has literally hundreds on its doorstep. Would definitely stay there again.

Reviewed on Apr 23, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,914, price is now $1,328 per person
$1,328
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
I had a wonderful stay at Aurum Uffizi. The staff were kind, friendly, and very helpful throughout my stay. The room was clean and comfortable, and the AC worked perfectly. The food was always fresh and enjoyable. Even though the hotel is close to shops, restaurants, and major tourist attractions, the area felt very safe and quiet, making it a perfect place to relax during my holiday. Highly recommended!

Reviewed on May 14, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $1,968, price is now $1,409 per person
$1,409
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (486 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $9,055, price is now $6,500 per person
$6,500
per person
Jun 19 - Jun 23
found 12 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (473 reviews)
Amazing service and staff. Wow!

Reviewed on Feb 21, 2026

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Discover the most popular places to visit in Castelfalfi

Castelfalfi Golf Course

Enjoy a round of golf in Castelfalfi at Castelfalfi Golf Course. Discover the beautiful countryside in this relaxing area.

Castelfalfi Golf Course

Monastery of San Vivaldo

Monastery of San Vivaldo is just one of the places to see in San Vivaldo, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and wineries in this relaxing area.

Monastery of San Vivaldo

What to do in Castelfalfi

Small Group Chianti Wineries Tuscan Lunch San Gimignano and more

Small Group Chianti Wineries Tuscan Lunch San Gimignano and more

$224
per adult
100% of travellers recommend
Small Group Chianti Wineries Tuscan Lunch San Gimignano and more
Discover San Miniato

Discover San Miniato

$42
per adult
Discover San Miniato
Vinci: wine-experience among the Tuscan hills

Vinci: wine-experience among the Tuscan hills

$41
per adult
Vinci: wine-experience among the Tuscan hills
See all activities in Castelfalfi

Castelfalfi Hotel Deals

Castelfalfi

Castelfalfi

5 out of 5
Loc. Castelfalfi Montaione FI
$942 nightly
The price is $1,048 total per night from May 18 to May 19
$1,048 total
May 18 - May 19
Total with taxes and fees
9.6/10 Exceptional! (165 reviews)
Excellent service, stunning property.

Reviewed on Apr 30, 2026

Castelfalfi
Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $76 total per night from Jun 4 to Jun 5
$76 total
Jun 4 - Jun 5
Total with taxes and fees
8.2/10 Very Good! (336 reviews)
We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, ...

Reviewed on Nov 27, 2025

Hotel Toscana Ambassador
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

3 out of 5
Loc. San Donato San Gimignano SI
$154 nightly
The price is $177 total per night from Jun 14 to Jun 15
$177 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (458 reviews)
We had the loveliest stay in Hotel Casolare! From the minute we arrived the staff were warm and welcoming and couldn't be more helpful! We stayed in the Cipresso apartment and it was perfect for the 4 of us staying with a well equipped kitchenette and a lovely patio area to sit out on! All very clean ...

Reviewed on May 6, 2026

Hotel Casolare Le Terre Rosse
See all 6,352 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 $1,310 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.