Montecastelli Vacations from $962

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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.
Hotel Villa Paradiso

Hotel Villa Paradiso

4 out of 5
per person
Oct 1 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Ancona (AOI)
7.6/10 Good! (86 reviews)
The hotel it’s really nice and staff

Reviewed on Jul 9, 2023

Natural Village Resort

Natural Village Resort

4 out of 5
per person
Sep 20 - Sep 24
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Ancona (AOI)
8.4/10 Very Good! (109 reviews)
It was so peaceful, entire facility from the private beach to the pool and family friendly property were top notch.

Reviewed on Jul 3, 2025

Hotel Priori Secret Garden

Hotel Priori Secret Garden

4 out of 5
Old Town Perugia
per person
Sep 20 - Sep 24
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Ancona (AOI)
9.6/10 Exceptional! (152 reviews)
In the heart of the action, yet removed enough to sleep like a baby, we had a fabulous stay at Priori Secret Garden. Looking forward to going back next year.

Reviewed on Jul 20, 2025

Hotel Perugia Plaza

Hotel Perugia Plaza

4 out of 5
per person
Sep 20 - Sep 24
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Ancona (AOI)
8.2/10 Very Good! (200 reviews)
Staff excellent. Would have been nice to get a coffee, tea or a drink in the lobby area.

Reviewed on May 17, 2025

Fortino Napoleonico

Fortino Napoleonico

4 out of 5
per person
Sep 20 - Sep 24
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Ancona (AOI)
9.4/10 Exceptional! (100 reviews)
Wonderful historical fort turned hotel. Beautiful gardens, rocky beach, crystal clear water. A private hidden gem we happened to stumble upon through Expedia.

Reviewed on Jul 20, 2025

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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

Umbria - Horse Riding Through The Wonderful Valleys Of Umbria, Lunch Included

Umbria, Horseback riding in the Umbrian countryside with lunch

$339
per adult
Umbria, Horseback riding in the Umbrian countryside with lunch
Cooking Class in a Historical Oil Mill near Trasimeno Lake

Cooking Class in a Historical Oil Mill near Trasimeno Lake

$153
per adult
Cooking Class in a Historical Oil Mill near Trasimeno Lake
Truffle hunting or Olive harvest - seasonal

Truffle hunting or Olive harvest - seasonal

$105
per adult
Truffle hunting or Olive harvest - seasonal
See all activities in Montecastelli

Montecastelli Hotel Deals

Hotel Sangallo Palace

Hotel Sangallo Palace

4 out of 5
Via L Masi 9, Perugia, PG
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $147 total per night from Aug 11 to Aug 12
$147 total
Aug 11 - Aug 12
Total includes taxes and fees
8.8/10 Excellent! (573 reviews)
"What a lovely hotel. Rooms really comfortable and balcony a surprise extra"

Reviewed on Aug 2, 2025

Hotel Sangallo Palace
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
$272 nightly
The price is $309 total per night from Aug 22 to Aug 23
$309 total
Aug 22 - Aug 23
Total includes taxes and fees
9.8/10 Exceptional! (227 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on Aug 7, 2025

Monastero di Cortona Hotel & Spa
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
$574 nightly
The price is $640 total per night from Aug 11 to Aug 12
$640 total
Aug 11 - Aug 12
Total includes taxes and fees
9.6/10 Exceptional! (218 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"

Reviewed on Jul 29, 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 3,174 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.

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Frequently asked questions

How much does a Montecastelli vacation package cost?
Offering excellent value package deals from $962 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.