Montecastelli Vacations from $1,599

Book a Hotel + Flight or Car together to unlock savings

Photo by LigaDue

Your Montecastelli Vacation

Get ready to experience Montecastelli in your own style with a custom Montecastelli vacation package! Discovering the treasures of this lively city is made simpler with a base in a neighborhood such as San Secondo, which is great for walking, among lots of other things. If a sightseeing tour is part of the program during your trip to Montecastelli, look around popular attractions like Villa Valentina Resort e Spa, Civitella Ranieri Castle and Santa Croce Museum. Check out Expedia's wide range of travel options and book your ultimate vacation to Montecastelli today.

The Latest Montecastelli vacation packages

Price found within the past 48 hours. Click for updated prices.
Casablanca Hotel

Casablanca Hotel

3 out of 5
Price was $1,623, price is now $1,599 per person
$1,599
per person
Jan 2 - Jan 5
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Ancona (AOI)
9.6/10 Exceptional! (27 reviews)
Owners and staff go out of the way to make you feel at home.

Reviewed on Jun 21, 2024

View Place & Spa

View Place & Spa

5 out of 5
Price was $1,687, price is now $1,652 per person
$1,652
per person
Jan 2 - Jan 5
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Ancona (AOI)
9.6/10 Exceptional! (33 reviews)
Un nuovissimo hotel

Reviewed on Jul 6, 2025

SeePort Hotel

SeePort Hotel

4 out of 5
Price was $1,650, price is now $1,623 per person
$1,623
per person
Jan 2 - Jan 5
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Ancona (AOI)
9.4/10 Exceptional! (443 reviews)
Perfect location and great views of the ocean

Reviewed on Sep 28, 2025

Pineta Hotel

Pineta Hotel

4 out of 5
Price was $1,642, price is now $1,616 per person
$1,616
per person
Jan 2 - Jan 5
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Ancona (AOI)
9.4/10 Exceptional! (232 reviews)
We drove in late in the evening and was delighted to wake up to a tasty breakfast buffet and the stunning location in the hills. It was a very spacious room with modern amenities.

Reviewed on Sep 26, 2025

Marino1958 RTA

Marino1958 RTA

3 out of 5
Price was $1,672, price is now $1,646 per person
$1,646
per person
Jan 2 - Jan 5
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Ancona (AOI)
8.8/10 Excellent! (3 reviews)
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

Civitella Ranieri Castle

You can find out about the history of Umbertide with a trip to Civitella Ranieri Castle. Make time to visit the spas and cathedral while you're in the area.

Civitella Ranieri Castle

Abbey San Salvatore di Montecorona

Learn about the local history of Umbertide when you take a trip to Abbey San Salvatore di Montecorona. In the area, take in the jazz scene and countryside.

Abbey San Salvatore di Montecorona

Villa Valentina Resort e Spa

You can take time to visit Villa Valentina Resort e Spa during your travels to Umbertide. Discover the area's countryside and spas.

Villa Valentina Resort e Spa

What to do in Montecastelli

Perugia: Old Town Walking Tour, Piazza IV Novembre

Perugia: Old Town Walking Tour, Piazza IV Novembre

$35
per adult
Perugia: Old Town Walking Tour, Piazza IV Novembre
Umbria: guided tour to traditional oil mill + tasting

Umbria: guided tour to traditional oil mill + tasting

$16
per adult
Umbria: guided tour to traditional oil mill + tasting
Perugia: San Lorenzo Cathedral Audioguide Tour

Perugia: San Lorenzo Cathedral Audioguide Tour

$5
per adult
Perugia: San Lorenzo Cathedral Audioguide Tour
See all activities in Montecastelli

Montecastelli Hotel Deals

Best Western Hotel Quattrotorri Perugia

Best Western Hotel Quattrotorri Perugia

4 out of 5
Via Corcianese 260, Perugia, PG
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Nov 30 to Dec 1
$111 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (340 reviews)
A lovely comfortable hotel
We chose this hotel because it was on the outskirts of Perugia and it had a carpark. It is a lovely comfortable modern hotel. The room was spotless when I moved in, but the bins weren't always emptied completely. The breakfast buffet was plentiful and varied. We tried the restaurant for dinner: it ...

Reviewed on Sep 6, 2025

Best Western Hotel Quattrotorri Perugia
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
$280 nightly
The price is $313 total per night from Nov 20 to Nov 21
$313 total
Nov 20 - Nov 21
Total with taxes and fees
9.8/10 Exceptional! (249 reviews)
Incredible hotel with amazing staff

Reviewed on Nov 1, 2025

Monastero di Cortona Hotel & Spa
Hotel Fortuna

Hotel Fortuna

3 out of 5
Via Bonazzi 19, Perugia, PG
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $113 total per night from Nov 9 to Nov 10
$113 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (527 reviews)
Fabulous location, great hotel

Reviewed on Oct 26, 2025

Hotel Fortuna
See all 3,099 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
Closest Airport
Sant Egidio Airport (PEG)
Top Sights
Civitella Ranieri Castle, Church of Santa Maria della Reggia and Villa Valentina Resort e Spa

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 excellent value package deals from $1,599 on Expedia, you'll be thrilled with how little a vacation to Montecastelli costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Montecastelli?
You're likely to find lower prices and better availability in August, November and December. Take a look at our cheap Montecastelli vacation packages and you could get some excellent off-season deals.
How many days is enough for Montecastelli?
The ideal length of your Montecastelli vacation depends on what you'd like to do and see. Generally, a few days to a week will give you plenty of time to go to all the major attractions and explore some hidden spots along the way.
How to find the best Montecastelli package deals?
Landing a cheap Montecastelli package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Montecastelli package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Montecastelli vacation as a package?
You can enjoy significant savings on your next Montecastelli retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Montecastelli?
If you have your Montecastelli vacation dates locked in, book as soon as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Montecastelli vacation packages?
Set off on your perfect trip to Montecastelli with our Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stick to your budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.