Trestina Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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$481 per night from 24 Aug to 25 Aug
S$481
24 Aug - 25 Aug
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on 7 Aug, 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
The price is S$844 per night from 23 Aug to 24 Aug
S$844
23 Aug - 24 Aug
includes taxes & fees
9.6/10 Exceptional! (219 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"

Reviewed on 29 Jul, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370, Cortona, AR
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (113 reviews)
"The propriety is one of the nicest I’ve stayed at. Very relaxing atmosphere, comfortable large pool area. Breakfast and lunch options are delicious. Room was very comfortable and spacious. The only problem I experienced was both adjacent rooms were smokers and did so on their patios. We couldn’t ..."

Reviewed on 14 Aug, 2025

Get rates
Il Falconiere - Relais e Chateaux
See all 3,323 properties in Trestina
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 Trestina

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

Umbria, Horseback riding in the Umbrian countryside with lunch

S$432
per adult
Umbria, Horseback riding in the Umbrian countryside with lunch
Cortona

Cortona Private Guided Tour

S$389
per traveller
Cortona Private Guided Tour
Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona

Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona

S$202
per adult
Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona
See all activities in Trestina

Frequently asked questions

How much does a Trestina holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday to Trestina costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Trestina?
January, February and March are the best times to look for cheap Trestina holiday packages. Opting to travel in quieter months means you'll typically find lower prices on flights and accommodation.
How many days is enough for Trestina?
The ideal duration for your Trestina holiday depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to tick off all the leading attractions and explore some hidden treasures along the way.
How to find the best Trestina package deals?
Start your search for a Trestina package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Trestina package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Trestina adventure underway.
Is it cheaper to book a Trestina holiday as a package?
You can enjoy significant savings on your next Trestina retreat by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. 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 Trestina?
If you're planning a spontaneous Trestina getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Trestina?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to visit Trestina.
  2. Calculate your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Trestina.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Trestina. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalised Trestina holiday package.

* 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.