Castelfiorentino Vacations from $1,095

Book a Hotel + Flight or Car together to unlock savings

Photo by Vanessa Sgaravizzi

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel Botticelli

Hotel Botticelli

4 out of 5
Historic Centre of Florence
Price was $1,460, price is now $1,095 per person
$1,095
per person
Dec 19 - Dec 23
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (980 reviews)
Booked a room for 1 and it was quite small, not worth the price for me but good location

Reviewed on Sep 25, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,749, price is now $1,186 per person
$1,186
per person
Dec 19 - Dec 23
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (477 reviews)
Superb hotel. Rooms magnificent, reflect the photos. Staff amazingly friendly and helpful.

Reviewed on Sep 27, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,025, price is now $1,389 per person
$1,389
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $1,731, price is now $1,275 per person
$1,275
per person
Nov 3 - Nov 8
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (51 reviews)
Property is beautiful and quiet. Would stay there again.

Reviewed on Sep 13, 2025

Hotel Ville sull'Arno

Hotel Ville sull'Arno

5 out of 5
Campo di Marte
Price was $1,481, price is now $1,103 per person
$1,103
per person
Dec 19 - Dec 23
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (748 reviews)
Exceptional staff and breakfast.

Reviewed on Sep 23, 2025

Don't see what you're looking for?
See all available trips from Columbus to Castelfiorentino
View all trips

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 quaint 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 relaxing area.

Teatro del Popolo

What to do in Castelfiorentino

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$141
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Discover San Miniato

Discover San Miniato

$42
per adult
Discover San Miniato
Private Wine & Oil Tasting with Lunch

Private Wine & Oil Tasting with Lunch

$74
per adult
Private Wine & Oil Tasting with Lunch
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
$161 nightly
The price is $194 total per night from Oct 31 to Nov 1
$194 total
Oct 31 - Nov 1
Total with taxes and fees
8.8/10 Excellent! (1,237 reviews)
"Great spot, pool view is epic!"

Reviewed on Sep 25, 2025

The Social Hub Florence Lavagnini
Hotel Machiavelli Palace

Hotel Machiavelli Palace

3 out of 5
Via Nazionale 10, Florence, FI
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $202 total per night from Oct 26 to Oct 27
$202 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (92 reviews)
"Place was in a busy area which was convenient, not so quiet, bathroom is very small. Staff were very nice and breakfast is a bonus."

Reviewed on Sep 27, 2025

Hotel Machiavelli Palace
c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3, Florence, FI
$198 nightly
The price is $235 total per night from Oct 31 to Nov 1
$235 total
Oct 31 - Nov 1
Total with taxes and fees
8.2/10 Very Good! (1,012 reviews)
"Great staff rooms a bit too different for my taste."

Reviewed on Sep 19, 2025

c-hotels Ambasciatori
See all 14,603 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Castelfiorentino vacation package cost?
Offering great value package deals from $1,095 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.