Santa Maria Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Santa Maria
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
S$691
29 Aug - 30 Aug
includes taxes & fees
9.6/10 Exceptional! (161 reviews)
"Horrible service at best. Not a 5 star hotel. Save your money."
Reviewed on 17 Aug, 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
S$1,003
29 Aug - 30 Aug
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on 17 Aug, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
S$483
3 Sept - 4 Sept
includes taxes & fees
10/10 Exceptional! (315 reviews)
"Amazing!!!! Very well kept place, the staff treats you like family. Room was cleaned fast in the morning. Restaurant and bar staff as well were amazing. The pool area is good vibes and the drinks and really good too 👍👍 I would definitely come back."
Reviewed on 21 Aug, 2026
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 Santa Maria
Oil museum and oil mill in Tuscany: tour and tasting
S$30
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
S$37
per adult
Tasting with Private Walk in a Cellar in Tuscany
S$37
per adult
Frequently asked questions
How much does a Santa Maria holiday package cost?
You'll find cheap prices on Expedia for your Santa Maria getaway. However, a range of factors like the season, choice of hotel and length of stay will determine how much your holiday to Santa Maria costs.
What are the cheapest months to go to Santa Maria?
If you're hoping to snag a cheap Santa Maria holiday package, consider travelling in January, February and March. You'll typically find better rates on flights and accommodation during these months — perfect for a budget-friendly break.
How many days is enough for Santa Maria?
The ideal duration for your Santa Maria holiday depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to tick off all the main attractions and explore some hidden treasures along the way.
How to find the best Santa Maria package deals?
Use Expedia's filter tool to help you find some fabulous Santa Maria package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Santa Maria package deals in the off-season. Play around with your travel dates and you may score 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 Santa Maria holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Santa Maria holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Santa Maria?
If you've got your Santa Maria holiday dates finalized, book early to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Santa Maria?
- Choose when to get away: Check your calendar and pack your bags. Your favourite season and the available activities will also help you decide when to escape to Santa Maria.
- Budget wisely: As well as the price of your accommodation, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Santa Maria.
- Decide how long to go away for: Now that you're up to speed on Santa Maria, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time for all the things you want to do.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Santa Maria holiday package that brings all your bookings together.
* 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.
