Montecastelli Vacations from $1,308

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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 $1,897, price is now $1,308 per person
$1,308
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Breakfast was ok but we found it difficult to get healthy food. There seemed to be a finite amount of fruit and yogurt (managed to get a yogurt one morning out of four). That said we opted for 8 am breakfast and might have had more luck earlier. Hotel was well located and felt really secure. I would stay there again.

Reviewed on Apr 13, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $5,741, price is now $3,626 per person
$3,626
per person
May 27 - Jun 2
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Absolutely an amazing stay. Very charming and well kept. Essentially a resort with a palatial feel. Loved walking the grounds and relaxing. Excellent restaurant, breakfast was included. The setting is quiet and beautiful. Will book again.

Reviewed on Apr 13, 2026

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Save 100% on your flight
Price was $4,460, price is now $3,113 per person
$3,113
per person
May 21 - May 26
found 13 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (192 reviews)
This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint

Reviewed on Sep 2, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,460, price is now $1,745 per person
$1,745
per person
May 23 - May 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Park Hotel Villa Ariston

Park Hotel Villa Ariston

4 out of 5
Price was $2,601, price is now $1,865 per person
$1,865
per person
Jun 19 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.8/10 Excellent! (128 reviews)
Amazing property with good facilities. Easy access to the beach and local restaurants. Simming pool is excellent and the staff very friendly. You can have a nice and peaceful stay there

Reviewed on Sep 8, 2024

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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
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $72 total per night from Apr 26 to Apr 27
$72 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (481 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
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
$141 nightly
The price is $162 total per night from Apr 26 to Apr 27
$162 total
Apr 26 - Apr 27
Total with taxes and fees
9.2/10 Wonderful! (452 reviews)
.

Reviewed on Apr 7, 2026

Hotel Casolare Le Terre Rosse
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
$130 nightly
The price is $149 total per night from Apr 28 to Apr 29
$149 total
Apr 28 - Apr 29
Total with taxes and fees
9/10 Wonderful! (332 reviews)
Below expectations for the price – nice location but disappointing experience We stayed for three nights in early April as a couple. During the same trip, we stayed in other agriturismos in a similar price range, and this one unfortunately did not compare well in terms of value and overall experience. ...

Reviewed on Apr 12, 2026

Poderi Arcangelo
See all 4,241 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 $1,308 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.