Montecastelli Vacations from $559

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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 $847, price is now $559 per person
$559
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
Breakfast was excellent

Reviewed on Sep 29, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $955, price is now $599 per person
$599
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Basic , clean and nice staff

Reviewed on Oct 10, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,577, price is now $1,835 per person
$1,835
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Park Palace

Park Palace

4 out of 5
Oltrarno
Price was $926, price is now $669 per person
$669
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9/10 Wonderful! (356 reviews)
Stayed here for four nights with my husband and it was amazing! The breakfast in the morning was delicious and the staff was so friendly and helpful. We loved that it was outside of the busyness of the city but close enough to have a taxi take us back and forth throughout the day. We had the hotel call us a taxi multiple times but also downloaded AppTaxi to get rides back to the hotel which was very convenient. The room was very comfortable and the pool area very peaceful - we loved coming here to wind down after exploring all day! I could not recommend this hotel more!!!

Reviewed on Oct 4, 2025

Palazzo Lorenzo Hotel Boutique & Spa

Palazzo Lorenzo Hotel Boutique & Spa

4 out of 5
San Lorenzo
Price was $1,079, price is now $811 per person
$811
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (585 reviews)
Beautiful hotel, clean room beautifully decorated and with everything needed to make our stay feel luxurious and comfortable. Friendly helpful staff. Delicious buffet breakfast and free use of spa facilities. It felt 5 star!

Reviewed on Sep 27, 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
$50 nightly
The price is $56 total per night from Nov 9 to Nov 10
$56 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (454 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on Jul 7, 2025

Hotel Ristorante Alcide
Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67, Siena, SI
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $103 total per night from Nov 9 to Nov 10
$103 total
Nov 9 - Nov 10
Total with taxes and fees
9/10 Wonderful! (983 reviews)
"The service was really the highlight of our stay. Everyone was so friendly and helpful! Our room was perfect and we really loved the large bathroom and shower. Breakfast was good and the service there was very good as well. A very enjoyable stay!"

Reviewed on Oct 7, 2025

Hotel Italia
RELAIS SANTA CHIARA - TUSCANY CHARME

RELAIS SANTA CHIARA - TUSCANY CHARME

4 out of 5
Via Giacomo Matteotti, 15, San Gimignano, SI
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $91 total per night from Nov 2 to Nov 3
$91 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (390 reviews)
"Perfect stay in San Gimiano - thank you! The reception staff are fantastic - polite and very helpful. We loved our balcony Will be back hopefully for longer"

Reviewed on Sep 24, 2025

RELAIS SANTA CHIARA - TUSCANY CHARME
See all 4,322 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.

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 $559 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.