Montecastelli Vacations from $1,052

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The Latest Montecastelli vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,426, price is now $1,052 per person
$1,052
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
The room was kept clean. The staff extremely nice and attentive. Breakfast was good and the dinning area very clean. It was walking distance from Academia gallery.

Reviewed on May 8, 2026

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $2,267, price is now $1,749 per person
$1,749
per person
Jul 25 - Jul 31
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (65 reviews)
I particularly love the authenticity of the building being hundreds of hundreds of years old and yet well cut, beautiful staff beautiful spa only lacking in the dining aspect but everything else was perfect. Highly recommend but recommend going out for dinner.

Reviewed on Nov 5, 2025

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $4,026, price is now $2,891 per person
$2,891
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (61 reviews)
Fabulous old building but fully refurbished with modern suites. Only 12 suites, all unique with 2 on each floor. Loads of room. Staff fabulous. Only minus point is there’s no bar or restaurant, but it is located within an area that has literally hundreds on its doorstep. Would definitely stay there again.

Reviewed on Apr 23, 2026

The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts

5 out of 5
Save 100% on your flight
Price was $3,375, price is now $2,487 per person
$2,487
per person
Jul 21 - Jul 27
found 6 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (211 reviews)
Everything was absolutely perfect and would definitely recommend a stay there. Can’t wait for a return visit.

Reviewed on May 5, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $1,993, price is now $1,480 per person
$1,480
per person
Jul 18 - Jul 24
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (993 reviews)
Absolutely perfect hotel - staff was simply amazing and so accommodating. The location was perfect, the room had great character and was very clean. We will certainly visit again.

Reviewed on May 9, 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 Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $77 total per night from Jun 4 to Jun 5
$77 total
Jun 4 - Jun 5
Total with taxes and fees
8.2/10 Very Good! (336 reviews)
We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, ...

Reviewed on Nov 27, 2025

Hotel Toscana Ambassador
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
$157 nightly
The price is $180 total per night from Jun 7 to Jun 8
$180 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (458 reviews)
We had the loveliest stay in Hotel Casolare! From the minute we arrived the staff were warm and welcoming and couldn't be more helpful! We stayed in the Cipresso apartment and it was perfect for the 4 of us staying with a well equipped kitchenette and a lovely patio area to sit out on! All very clean ...

Reviewed on May 6, 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
$115 nightly
The price is $132 total per night from Jun 8 to Jun 9
$132 total
Jun 8 - Jun 9
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
Through all my travels in Italy, this was probably the nicest accommodations. Centrally located and near the train station, large room and excellent breakfast.

Reviewed on May 11, 2026

Hotel Italia
See all 4,266 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 $1,052 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.