Castelfiorentino Vacations from $748

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Your Castelfiorentino Vacation

Reserve a Castelfiorentino vacation package that includes everything you need without any unnecessary extras. Good for walking, views and nature, think about basing yourself in the neighborhood of Montelupo Fiorentino. If your trip to Castelfiorentino includes a little sightseeing, hit up much-loved attractions like Castello Sonnino, Teatro del Popolo and Castle of Oliveto. Whoever you're traveling with and whatever your budget, your ultimate Castelfiorentino vacation is just a few clicks away with Expedia.

The Latest Castelfiorentino vacation packages

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great location and very clean

Reviewed on Aug 12, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (218 reviews)
AMAZING! Gorgeous! I would recommend to everyone!

Reviewed on Jul 29, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.

Reviewed on Aug 14, 2025

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Discover the most popular places to visit in Castelfiorentino

Benozzo Gozzoli Museum

You can spend an afternoon studying the exhibits at Benozzo Gozzoli Museum in Castelfiorentino. Discover the beautiful countryside and wineries in this relaxing area.

Benozzo Gozzoli Museum

Teatro del Popolo

You can make plans for a show at Teatro del Popolo during your stay in Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area.

Teatro del Popolo

What to do in Castelfiorentino

Having fun while tasting Chianti

Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

$221
per adult
100% of travellers recommend
Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence
Students and family friendly tours

Tuscany Vespa Tour from Florence with Wine Tasting

$232
per adult
100% of travellers recommend
Tuscany Vespa Tour from Florence with Wine Tasting
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$138
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
See all activities in Castelfiorentino

Castelfiorentino Hotel Deals

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72, Florence, FI
Fully refundable
$116 nightly
The price is $144 total per night from Aug 29 to Aug 30
$144 total
Aug 29 - Aug 30
Total includes taxes and fees
8.8/10 Excellent! (1,129 reviews)
"Great location. Beautiful view and pool. Pool closes pretty early."

Reviewed on Aug 13, 2025

The Social Hub Florence Lavagnini
c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3, Florence, FI
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $126 total per night from Aug 31 to Sep 1
$126 total
Aug 31 - Sep 1
Total includes taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Very good location. Ideal for the train station and walking into Florence. Very nice dinning area and breakfast selection. Can get a little crowded outside the hotel with people waiting for trams/buses. But that’s no fault of the hotel."

Reviewed on Aug 13, 2025

c-hotels Ambasciatori
Hotel Machiavelli Palace

Hotel Machiavelli Palace

3 out of 5
Via Nazionale 10, Florence, FI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $104 total per night from Aug 18 to Aug 19
$104 total
Aug 18 - Aug 19
Total includes taxes and fees
8.6/10 Excellent! (68 reviews)
"The hotel and staff were excellent. The hotel is very near the train station and all the main items are within walking distance."

Reviewed on Aug 9, 2025

Hotel Machiavelli Palace
See all 14,596 properties in Castelfiorentino
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.

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Frequently asked questions

How much does a Castelfiorentino vacation package cost?
Offering great value package deals from $748 on Expedia, you'll be thrilled with how little a vacation to Castelfiorentino costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Castelfiorentino?
November, December and January are great times to look for cheap Castelfiorentino vacation packages. Opting to travel in quieter periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Castelfiorentino?
When planning your Castelfiorentino vacation, a few days will be enough to tour the top spots. Be sure to stop by Benozzo Gozzoli Museum — it's one of the major attractions in this destination. If you want more activities, consider basing yourself here and setting off on some day trips from Castelfiorentino.
Is it worth booking a vacation package to Castelfiorentino?
Castelfiorentino has all the ingredients you need for the perfect break — walking trails, history and views are just the start. Whether you want to check out sights such as Castle of Oliveto and Teatro del Popolo, or take the path less traveled, there's plenty to explore on your Castelfiorentino vacation.
How to find the best Castelfiorentino package deals?
Finding a cheap Castelfiorentino package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Castelfiorentino package deals. Want a simple trick to get 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 Castelfiorentino vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels individually. Better still, you can personalize your Castelfiorentino escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Castelfiorentino?
Score fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Castelfiorentino adventure.
How to plan a trip to Castelfiorentino?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to visit Castelfiorentino.
  2. Plan your budget wisely: As well as the cost of your accommodations, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may crop up during your trip to Castelfiorentino.
  3. Use our trip planning tool to discover Castelfiorentino: Research every part of your trip to Castelfiorentino with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you're more familiar with Castelfiorentino, you can work out the perfect length of your vacation. Put together a rough plan and give yourself enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Castelfiorentino vacation package.
  6. Book activities and experiences ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on Castelfiorentino's highlights. Find all the incredible things to do in Castelfiorentino with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Castelfiorentino vacation packages?
If you're like us, you love exploring new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Castelfiorentino trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure 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.