Villastrada Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Villastrada

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$432 per night from 24 Aug to 25 Aug
S$432
24 Aug - 25 Aug
includes taxes & fees
9.8/10 Exceptional! (229 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on 7 Aug, 2025

Monastero di Cortona Hotel & Spa
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (582 reviews)
"Great experience"

Reviewed on 13 Aug, 2025

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Hotel Relais II Chiostro di Pienza
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$845 per night from 23 Aug to 24 Aug
S$845
23 Aug - 24 Aug
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"

Reviewed on 29 Jul, 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 4,599 properties in Villastrada
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 Villastrada

Wine Tasting & Tour Premium

Wine Tasting & Tour Premium

S$69
per adult
Wine Tasting & Tour Premium
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

S$133
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

S$78
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
See all activities in Villastrada

Frequently asked questions

How much does a Villastrada holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Villastrada costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Villastrada?
January, February and March are the best times to look for cheap Villastrada holiday packages. Travelling in less busy months means you can generally find better prices on flights and hotels.
How many days is enough for Villastrada?
The ideal length for your Villastrada holiday depends on what you'd like to do and see. Usually, a few days to a week will give you time to visit all the top attractions and discover some hidden spots along the way.
How to find the best Villastrada package deals?
Use Expedia's handy filters to find some of the best Villastrada package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Villastrada package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Villastrada holiday as a package?
You can enjoy significant savings on your Villastrada break by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Villastrada?
If you have your Villastrada holiday dates locked in, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Villastrada?

  1. Choose when to travel: Check your diary and get packing. Your preferred time of year and the activities on offer will also help you decide when to visit Villastrada.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Villastrada.
  3. Decide how long to go for: Now that you're up to speed on Villastrada, you can work out the right length of your holiday. Pull together a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Villastrada 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.