Montecastelli Vacations from $914

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The Latest Montecastelli 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 $1,397, price is now $914 per person
$914
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
The room was clean and the staff was extra helpful with touring suggestions. They were also helpful with directions.

Reviewed on Jun 26, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,117, price is now $1,271 per person
$1,271
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Room was clean and bed was comfortable however windows weren't soundproof. Location is fantastic. Fire alarm went off multiple times during my stay including once in the middle of the night. Breakfast was very basic.

Reviewed on Jun 29, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,395, price is now $1,459 per person
$1,459
per person
Sep 19 - Sep 24
found 2 days ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.8/10 Excellent! (1,001 reviews)
We had a wonderful stay at this hotel in Florence. From the moment we arrived, the staff was kind, welcoming, and very helpful. The communication before and during our stay was excellent, which made everything feel smooth and easy. The location was perfect for enjoying Florence, and the hotel itself felt comfortable, clean, and well cared for. After long days walking through the city, it was a great place to come back to and relax. What stood out most was the hospitality. The staff made us feel taken care of without it ever feeling forced. You can tell they genuinely care about their guests having a great experience. We would absolutely stay here again and highly recommend it to anyone visiting Florence.

Reviewed on Jun 16, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,264, price is now $2,721 per person
$2,721
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $4,318, price is now $2,784 per person
$2,784
per person
Sep 19 - Sep 24
found 2 days ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (548 reviews)
Beautiful hotel in a perfect location.

Reviewed on Jun 13, 2026

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Montecastelli Hotel Deals

Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Jul 29 to Jul 30
$104 total
Jul 29 - Jul 30
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the ..."

Reviewed on Jun 27, 2026

Hotel Italia
Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $78 total per night from Jul 6 to Jul 7
$78 total
Jul 6 - Jul 7
Total with taxes and fees
8.2/10 Very Good! (347 reviews)
"Room was clean, staff was helpful and easy to park."

Reviewed on Jun 27, 2026

Hotel Toscana Ambassador
Mormoraia

Mormoraia

Agriturismo San Gimignano San Gimignano SI
$279 nightly
The price is $313 total per night from Jun 30 to Jul 1
$313 total
Jun 30 - Jul 1
Total with taxes and fees
Mormoraia
See all 4,435 properties in Montecastelli
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 Montecastelli Vacation Packages

Montecastelli Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Max Temp Winter
50ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does a Montecastelli vacation package cost?
Offering great value package deals from $914 on Expedia, you'll be thrilled with how little a vacation to Montecastelli costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Montecastelli?
November, December and January are great times to search for cheap Montecastelli vacation packages. Opting to travel in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Montecastelli?
The ideal length of your Montecastelli vacation depends on what you'd like to do. Usually, a handful of days to a week will give you time to go to all the leading sights and explore some hidden spots along the way.
How to find the best Montecastelli package deals?
Landing a cheap Montecastelli package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Montecastelli package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Montecastelli 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 tailor your Montecastelli trip to fit 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 Montecastelli?
If you're planning a spontaneous Montecastelli vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Montecastelli vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Montecastelli trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great 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.