Montecastelli Vacations from $924
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The Latest Montecastelli vacation packages
Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique
Historic Centre of Florence
$1,462
per person
Oct 22 - Oct 27
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (500 reviews)
mattresses were impossible to sleep on
Reviewed on Sep 14, 2026
Palazzo Castri 1874 Spa & Garden
Historic Centre of Florence
$967
per person
Nov 19 - Nov 25
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,003 reviews)
Highly recommend this. While short walk to everywhere in the city, the garden and pool are so secluded you get the best of both worlds. Breakfast was included, and having late night wine in the garden could not have been more perfect
Reviewed on Sep 12, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
$1,012
per person
Nov 9 - Nov 14
found 12 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
We had a wonderful stay at The Moon hotel. The staff are excellent and we had a speedy and very easy check in experience. The Moon is a beautiful, calm place slightly out of the central sights of Florence, but within an easy walk. Our rooms were beautiful. Great showers and the beds were so comfortable. We slept very well. Breakfast was of a high quality, the fresh egg dishes were delicious. If you like cake for breakfast, you will be spoilt for choice. We used the spa area which was lovely at the end of the day. If not included in your room deal it is extra and you need to book a slot. The hydrotherapy pool is not huge, but works well. Sauna and steam room were very good. Overall a wonderful experience and special thanks to Giorgio for his quick check in and excellent and friendly customer service throughout our stay.
Reviewed on Sep 13, 2026
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Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$120 nightly
$138 total
Oct 11 - Oct 12
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Clean, well maintained property that you’ll feel safe spending the night."
Reviewed on Sep 12, 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
$121 nightly
$139 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (368 reviews)
"Most of the staff were not pleasant. We had issues checking in. They gave us a smaller room than we booked and then had to pay to upgrade to an apartment which was all they had available that was bigger. Service at supper was not good. Food was good one night and not the other. Rooms smell musty. ..."
Reviewed on Sep 16, 2026
Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
$142 nightly
$163 total
Oct 13 - Oct 14
Total with taxes and fees
9.2/10 Wonderful! (487 reviews)
"If you are driving around in Tuscany and need a place to stay, look no further! The place is beautiful, clean, friendly staff and feels like a 5 star hotel without the price. location was central to all the wineries and Tuscany sites. Breakfast was fantastic. Awesome place!"
Reviewed on Sep 15, 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 $924 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.
