Montecastelli Vacations from $1,015

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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 $1,483, price is now $1,015 per person
$1,015
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.4/10 Good! (1,016 reviews)

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $1,385, price is now $1,063 per person
$1,063
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (508 reviews)

The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was $1,517, price is now $1,082 per person
$1,082
per person
Jan 18 - Jan 25
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Staff lovely, chatty, smiley, helpful. Food good if a little limited evening choice if staying more than a few nights (but so many other retaurants around) Bathroom great hot water but decor could be sharper - bit tatty in couple of places. Superior room as the picture, comfy bed and pillows. Trouble with mosquitos which could have been living in the aircon vents (take a swatter and anti bite - may just be a bad year) Good quiet area away from centre but easily walkable, tram very close. It has a bright, welcoming and relaxed atmosphere.

Reviewed on Oct 28, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,071, price is now $1,481 per person
$1,481
per person
Dec 30 - Jan 4
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (612 reviews)
Everything was wonderful about our stay at The Moon Hotel and Spa. The room was beautiful and clean, the staff were friendly and helpful and it was a great location for sightseeing in Florence. We especially appreciated the very generous breakfast that was always served efficiently and with a smile. We would definitely stay again.

Reviewed on Oct 23, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,502, price is now $1,108 per person
$1,108
per person
Jan 18 - Jan 25
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location, very clean and beautiful views. Staff was very kind and helpful

Reviewed on Oct 28, 2026

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Montecastelli Hotel Deals

Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Nov 29 to Nov 30
$77 total
Nov 29 - Nov 30
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the ..."

Reviewed on Oct 21, 2026

Hotel Italia
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Nov 13 to Nov 14
$123 total
Nov 13 - Nov 14
Total with taxes and fees
Poderi Arcangelo
Hotel Borgo San Luigi

Hotel Borgo San Luigi

4 out of 5
STRADA DELLA CERRETA,7 Monteriggioni SI
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Nov 8 to Nov 9
$129 total
Nov 8 - Nov 9
Total with taxes and fees
9.2/10 Wonderful! (455 reviews)
"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. ..."

Reviewed on Oct 25, 2026

Hotel Borgo San Luigi
See all 4,245 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 $1,015 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.