Montecastelli Vacations from $937
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The Latest Montecastelli vacation packages
Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Historic Centre of Florence
$937
per person
Nov 8 - Nov 14
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The room was clean, staff reasonably friendly, breakfast breads were stale, air conditioning worked well. Conveniently located for train station
Reviewed on Sep 2, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$969
per person
Nov 9 - Nov 14
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,010 reviews)
Had a great stay! Staff was friendly and helpful. Room was clean and updated.
Reviewed on Sep 4, 2026
Eden Rock Resort
$1,479
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on Jul 18, 2026
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Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
$129 nightly
$148 total
Sep 11 - Sep 12
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Our stay was fantastic. The room was genuinely luxurious with marble fittings everywhere. The staff were brilliant and really knew what to recommend. The breakfast was good but rather crowded on the day we were there."
Reviewed on Sep 2, 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
$124 nightly
$142 total
Sep 28 - Sep 29
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
Hotel Pescille by Double Hospitality
Strada Statale 47 San Gimignano SI
$126 nightly
$145 total
Oct 6 - Oct 7
Total with taxes and fees
9.2/10 Wonderful! (369 reviews)
"Superb stay, lovely pool, views are amazing, really nice breakfast and evening meal. Highly recommended."
Reviewed on Jun 18, 2026
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 $937 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.
