Montecastelli Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Montecastelli

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
The price is S$989 per night from 29 Jul to 30 Jul
S$989
29 Jul - 30 Jul
includes taxes & fees
9.8/10 Exceptional! (240 reviews)
"10/10"

Reviewed on 7 Jul, 2026

Villa di Piazzano - Small Luxury Hotel of the World
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
The price is S$469 per night from 11 Aug to 12 Aug
S$469
11 Aug - 12 Aug
includes taxes & fees
10/10 Exceptional! (293 reviews)
"There are really no words for how amazing this resort truly is. From the second we walked through the doors, it exceeded five-star service. From the staff, to the room, to the resort amenities, to the restaurants, they don’t miss a single detail. Our stay has been so amazing that we extended our ..."

Reviewed on 12 Jul, 2026

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370 Cortona AR
The price is S$523 per night from 31 Jul to 1 Aug
S$523
31 Jul - 1 Aug
includes taxes & fees
9.4/10 Exceptional! (133 reviews)
"Ok"

Reviewed on 8 Jul, 2026

Il Falconiere - Relais e Chateaux
See all 3,092 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.

What to do in Montecastelli

Perugia: Old Town Walking Tour, Piazza IV Novembre

Perugia: Old Town Walking Tour, Piazza IV Novembre

S$44
per adult
Perugia: Old Town Walking Tour, Piazza IV Novembre
Perugia: Chapter Museum Entry Ticket

Perugia: Chapter Museum entry ticket

S$12
per adult
Perugia: Chapter Museum entry ticket
Perugia Walking Tour with Audio and Written Guide by a local

Perugia Walking Tour with Audio and Written Guide by a local

S$10
per adult
100% of travellers recommend
Perugia Walking Tour with Audio and Written Guide by a local
See all activities in Montecastelli

Frequently asked questions

How much does a Montecastelli holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Montecastelli costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Montecastelli?
January, February and March are great times to search for cheap Montecastelli holiday packages. Choosing to travel in less busy months means you'll typically find reduced prices on flights and accommodation.
How many days is enough for Montecastelli?
Generally, a handful of days is enough to go to the top sights during your Montecastelli holiday. However, if you prefer to have more time to unwind or go on day trips, consider extending your itinerary.
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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Montecastelli holiday as a package?
You can enjoy significant savings on your next Montecastelli retreat by booking a personalised holiday 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 holiday package to Montecastelli?
If you have your Montecastelli holiday 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.
How to plan a trip to Montecastelli?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Montecastelli.
  2. Set your budget: Factor in expenses such as transportation, flights and meals when calculating how much to put aside for your trip to Montecastelli. Then, choose a property that matches your budget, whether that's a wallet-friendly option or a more luxurious getaway.
  3. Decide your trip length: Consider how long you'd like to spend exploring Montecastelli. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the perfect Montecastelli holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.