Montecastelli Vacations from $1,395

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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 $1,983, price is now $1,395 per person
$1,395
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Clean room and bathroom and confortable bed and pillows, perfect to be happy after a busy and wonderful day! The location is very convenient and safe, with too many restaurants around. No AC but if is cold outside you will be fine :)

Reviewed on Apr 25, 2026

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $15,479, price is now $10,500 per person
$10,500
per person
May 26 - Jun 1
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (473 reviews)
Amazing service and staff. Wow!

Reviewed on Feb 21, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,049, price is now $1,419 per person
$1,419
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Location is great, walking-distance to main attractions. Breakfast could be much better. Staff was always friendly and helpful. Room was clean although some mosquitoes were around the bathroom.

Reviewed on Apr 21, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,229, price is now $1,555 per person
$1,555
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (484 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

Hotel Palazzo Ognissanti

Hotel Palazzo Ognissanti

4 out of 5
Historic Centre of Florence
Price was $2,536, price is now $1,832 per person
$1,832
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (491 reviews)
Very clean room. Helpful staff

Reviewed on Jan 24, 2026

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Discover the most popular places to visit in Montecastelli

Biolago Geotermico Acqua Harda

You can take time to visit Biolago Geotermico Acqua Harda during your travels to Sasso Pisano. Discover the area's countryside and spas.

Biolago Geotermico Acqua Harda

Montecastelli Hotel Deals

Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

3 out of 5
Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $167 total per night from May 6 to May 7
$167 total
May 6 - May 7
Total with taxes and fees
9.2/10 Wonderful! (455 reviews)
Great staff who were amazing with my 1 year old. Beautiful grounds and the patio area outside the room was lovely and gave us some free time whilst baby slept. The bar food and breakfast was excellent and the restarting on the 2nd evening was equally has good. Thank you!!

Reviewed on Apr 21, 2026

Hotel Casolare Le Terre Rosse
Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $159 total per night from May 15 to May 16
$159 total
May 15 - May 16
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Excellent staff, great location, wonderful breakfast.

Reviewed on Apr 23, 2026

Hotel Italia
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $148 total per night from Apr 28 to Apr 29
$148 total
Apr 28 - Apr 29
Total with taxes and fees
9/10 Wonderful! (334 reviews)
Grounds are stunning with views in all direction's! Room is nice and big with a gorgeous view. Breakfast buffet is ok, dinner wasn’t that great, especially for the price. Quick 15 minute drive into San Gimignano. Pool area wasn’t open yet when we were there but looks great for when it is!

Reviewed on Apr 21, 2026

Poderi Arcangelo
See all 4,252 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 $1,395 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.