Montecastelli Vacations from $994

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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 $1,353, price is now $994 per person
$994
per person
Feb 5 - Feb 10
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.4/10 Good! (1,016 reviews)
Nice place, good location

Reviewed on Nov 11, 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was $1,582, price is now $1,222 per person
$1,222
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (177 reviews)
We loved the location and proximity to major attractions and great restaurants. Breakfast in the morning was delicious and in a lovely space. Our room was spacious, unfortunately it smelled like mildew. Our travel companions had the room next door which did not have the same issue. We also experienced a lot of noise in the middle of the night on two of the four nights we stayed. Overall, I would recommend this hotel, just a different hotel room in the future.

Reviewed on Nov 3, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was $2,754, price is now $1,915 per person
$1,915
per person
Feb 5 - Feb 10
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (82 reviews)
Great boutique hotel with good size room and bathroom. Very clean and helpful staff. Would definitely stay here again.

Reviewed on Nov 9, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,480, price is now $1,039 per person
$1,039
per person
Feb 5 - Feb 10
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,003 reviews)

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $4,413, price is now $3,147 per person
$3,147
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Amazing location. So cool to be literally across from the Duomo. Easy walk to so many places to shop and eat. Free sparkling and still water was great. Snacks and free gelato! Staff was the most friendly and helpful. Highly recommend this place!

Reviewed on Nov 3, 2026

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Montecastelli Hotel Deals

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 13 to Nov 14
$124 total
Nov 13 - Nov 14
Total with taxes and fees
Poderi Arcangelo
Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $79 total per night from Dec 13 to Dec 14
$79 total
Dec 13 - Dec 14
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Staff at front desk very helpful and breakfast was very good kitchen staff. Dry attentive. Close walk to downtown and plazza"

Reviewed on Nov 8, 2026

Hotel Italia
La Cisterna

La Cisterna

3 out of 5
Piazza Della Cisterna 23 San Gimignano SI
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $104 total per night from Nov 13 to Nov 14
$104 total
Nov 13 - Nov 14
Total with taxes and fees
La Cisterna
See all 4,188 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 $994 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.