Montecastelli Vacations from $727

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Montecastelli vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,155, price is now $727 per person
$727
per person
Mar 27 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great Locations walkable to all the placese.

Reviewed on Dec 15, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Price was $3,342, price is now $2,024 per person
$2,024
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,358, price is now $852 per person
$852
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (476 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Grand Hotel Baglioni

Grand Hotel Baglioni

4 out of 5
Historic Centre of Florence
Price was $2,371, price is now $1,493 per person
$1,493
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Very good hotel in a fantastic location. Meters from all the sites. Rooms and service excellent. Best breakfast in Italy.

Reviewed on Jan 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Montecastelli
View all trips

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
$50 nightly
The price is $56 total per night from Jan 18 to Jan 19
$56 total
Jan 18 - Jan 19
Total with taxes and fees
8/10 Very Good! (462 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
Hotel Borgo San Luigi

Hotel Borgo San Luigi

4 out of 5
STRADA DELLA CERRETA,7 Monteriggioni SI
$121 nightly
The price is $142 total per night from Feb 4 to Feb 5
$142 total
Feb 4 - Feb 5
Total with taxes and fees
9.2/10 Wonderful! (401 reviews)
Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended!

Reviewed on Dec 3, 2025

Hotel Borgo San Luigi
Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Jan 14 to Jan 15
$75 total
Jan 14 - Jan 15
Total with taxes and fees
8/10 Very Good! (312 reviews)
We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, ...

Reviewed on Nov 27, 2025

Hotel Toscana Ambassador
See all 4,033 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Montecastelli vacation package cost?
Offering great value package deals from $727 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.