Santa Maria Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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 Flight + Hotel Deals in Santa Maria

Price found within the past 48 hours. Click for updated prices.
Hotel San Luca

Hotel San Luca

4 out of 5
Cortona Old Town
Price was €655, price is now €500 per person
€500
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (434 reviews)
Wonderful place to stay in Cortona Great breakfast

Reviewed on 23 Jul 2026

Villa Neroli

Villa Neroli

4 out of 5
Coverciano
Save 100% on your flight
Price was €1,253, price is now €849 per person
€849
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (636 reviews)
We loved this place! We are a family of 4 and got a joined room. It was lovely. Would stay here again.

Reviewed on 14 Jul 2026

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
San Lorenzo
Save 100% on your flight
Price was €1,253, price is now €858 per person
€858
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,461 reviews)
Very nice hotel in a nice part of town. The best two features were the pool overlooking Florence and the gym, also with fantastic views.

Reviewed on 23 Jul 2026

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Save 100% on your flight
Price was €1,145, price is now €820 per person
€820
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (499 reviews)
The resort is absolutely gorgeous and tranquil. We loved the pool, the delicious breakfast included with our stay in the spacious king suite with its own huge patio! Wish we were able to stay longer!

Reviewed on 23 Jul 2026

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Santa Maria Novella
Price was €1,047, price is now €954 per person
€954
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (627 reviews)
A

Reviewed on 23 Jul 2026

Top hotels in Santa Maria

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is €701 per night from 5 Aug to 6 Aug
€701
5 Aug - 6 Aug
includes taxes & fees
9.6/10 Exceptional! (154 reviews)
"Magical location, pools, staff, property."

Reviewed on 19 Jul 2026

Precise Tale Poggio Alla Sala
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 €671 per night from 18 Aug to 19 Aug
€671
18 Aug - 19 Aug
includes taxes & fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"

Reviewed on 15 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 €366 per night from 16 Aug to 17 Aug
€366
16 Aug - 17 Aug
includes taxes & fees
10/10 Exceptional! (296 reviews)
"The food was amazing in the hotel. Staff was amazing. We felt at home from the moment we walked in. The amenities were wonderful."

Reviewed on 14 Jul 2026

Monastero di Cortona Hotel & Spa
See all 5,189 properties in Santa Maria
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

2-Hour Private Wine Tasting in the Cellar in Mugliano

Private Tasting of Organic Wines in the Cellar in Mugliano

€30
per adult
Private Tasting of Organic Wines in the Cellar in Mugliano
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

€20
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

€25
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
See all activities in Santa Maria

Frequently asked questions

How much does a Santa Maria holiday package cost?
You'll find cheap prices from €500 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.