Montecastelli Vacations from $1,009
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The Latest Montecastelli vacation packages
Price found within the past 48 hours. Click for updated prices.
Grand Hotel Cavour
Historic Centre of Florence
$1,199
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Wonderful, central hotel (we walked from the train station and only yards from the Doumas) with really helpful staff who recommended a fantastic restaurant when we explained the kind of thing we were looking for. Very classic decor style. Great breakfast. Surely the best rooftop bar in town and it gives priority to residents, even letting us take our children up. Would thoroughly recommend.
Reviewed on Aug 28, 2026
The Sense Experience Resort - Preferred Hotels & Resorts
$1,641
per person
Oct 5 - Oct 10
found 2 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (228 reviews)
Best sand beach in Italy :), Superior rooms have no views and are relatively Dark… Breakfast was very good. No comment to Staff
Reviewed on Aug 17, 2026
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Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$110 nightly
$127 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Staff were most courteous, both at front desk (local map offered on checkin) and in breakfast room. Breakfast buffet offered plenty of choices. Room and bathroom clean and tidy. City attractions dispersed throughout city, but walking made them accessible."
Reviewed on Aug 25, 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
$137 nightly
$156 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (367 reviews)
"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the ..."
Reviewed on Aug 26, 2026
Villa Ermellina Siena, a Tribute Portfolio Hotel
Via Custoza 2 Siena SI
Fully refundableReserve now, pay when you stay
$234 nightly
$263 total
Sep 1 - Sep 2
Total with taxes and fees
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 $1,009 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.
