Montecastelli Vacations from $749

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The Latest Montecastelli 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
Price was $1,087, price is now $749 per person
$749
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
19.2/10 Exceptional! (495 reviews)
Everything—the breakfast, the staff, and the cleanliness—was perfect. The room was quiet and supremely comfortable. Highly recommend!

Reviewed on Nov 17, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,676, price is now $1,568 per person
$1,568
per person
Feb 16 - Feb 22
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
19.6/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,221, price is now $760 per person
$760
per person
Feb 8 - Feb 14
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
15.6/10 Exceptional! (1,000 reviews)
Breakfast was good. Staff super friendly. Overall the expected quality for the paid price.

Reviewed on Nov 20, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was $1,264, price is now $873 per person
$873
per person
Feb 8 - Feb 14
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
19.2/10 Exceptional! (1,001 reviews)
Amazing location along the river, sandwiched between the Ponte Vecchio and the Uffizi, and a short walk to many of Florence’s highlights. We were in the new building which was very nice but lacking the charm of the original building. Breakfast was great and the staff were all lovely.

Reviewed on Nov 19, 2025

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,462, price is now $1,010 per person
$1,010
per person
Feb 16 - Feb 22
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
18.4/10 Exceptional! (1,002 reviews)
Wonderful staff, Great location, and the rooms were nice!

Reviewed on Nov 24, 2025

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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 Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A Poggibonsi SI
Fully refundableReserve now, pay when you stay
$52 nightly
The price is $57 total per night from Nov 30 to Dec 1
$57 total
Nov 30 - Dec 1
Total with taxes and fees
8/10 Very Good! (460 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
RELAIS SANTA CHIARA - TUSCANY CHARME

RELAIS SANTA CHIARA - TUSCANY CHARME

4 out of 5
Via Giacomo Matteotti, 15 San Gimignano SI
8.6/10 Excellent! (417 reviews)
The breakfast had lovely pastries, fruit and cheese. Staff were friendly. The view - stunning.

Reviewed on Oct 24, 2025

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RELAIS SANTA CHIARA - TUSCANY CHARME
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 Nov 30 to Dec 1
$79 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (983 reviews)
Highly recommended. The hotel was a block from the escalator flight that comes up from the train station, so no taxi required to transfer. Hotel staff was terrific and the room nicely appointed. I was about a 20-minute walk to the Duomo, almost all of it through the historic medieval city so a beautiful ...

Reviewed on Nov 7, 2025

Hotel Italia
See all 4,076 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 $749 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.