Val d'Orcia Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top hotels in Val d'Orcia

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
The price is S$121 per night from 16 Mar to 17 Mar
S$121
16 Mar - 17 Mar
includes taxes & fees
8.8/10 Excellent! (635 reviews)
A little tired, extremely clean, with an amazing staff

Reviewed on 1 Jan, 2026

Hotel Relais II Chiostro di Pienza
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Fully refundableReserve now, pay when you stay
The price is S$214 per night from 23 Mar to 24 Mar
S$214
23 Mar - 24 Mar
includes taxes & fees
9.4/10 Exceptional! (135 reviews)
Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!

Reviewed on 25 Oct, 2025

Hotel San Gregorio
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is S$1,596 per night from 21 Mar to 22 Mar
S$1,596
21 Mar - 22 Mar
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
See all 626 properties in Val d'Orcia
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.

Popular places to visit

Abbazia di Sant'Antimo

5/5(1 review)

You can learn about the history of Montalcino with a visit to Abbazia di Sant'Antimo. Visit the area's spas or simply enjoy its wineries.

Abbazia di Sant'Antimo

What to do in Val d'Orcia

Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

S$37
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Montalcino, Pienza & Montepulciano Wine & Food Tour

Tuscany Wine & Hills from Florence

S$192
per adult
84% of travellers recommend
Tuscany Wine & Hills from Florence
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

S$67
per adult
Montalcino: Guided Winery Tour and Wine Tasting
See all activities in Val d'Orcia

Frequently asked questions

Can I cancel my flight booking to Val d'Orcia due to COVID-19?
In these times of uncertainty, many carriers are offering greater flexibility. Head to our Customer Service Portal for important information about changing or cancelling your booking due to COVID-19.
What's the best way to find cheap flights to Val d'Orcia that have flexible change policies?
At Expedia, we've been channeling our inner Olympic gymnast to offer you the most flexible fares in town. Just tick the "No change fee" box directly under the filter heading "Flexible change policies" to find your ideal flight to Val d'Orcia.
What are some of the general tips for travellers to Val d'Orcia during the COVID-19 outbreak?
COVID-19 has led to major changes to the way we travel. If you're planning a holiday in Val d'Orcia, the following tips will help you navigate these new challenges and rules:
  • Find out if any travel restrictions apply to your origin and destination before booking your flight. Also check if there are any conditions you'll have to follow on arrival, such as taking a COVID-19 test.
  • When you pass through airport checkpoints, do not remove your face mask. You will be required to briefly lower it to confirm your identity. Passengers who refuse to wear a mask may face civil penalties and may also be escorted from the building.
  • You're no longer required to hand your boarding pass directly to a TSA employee. Instead, position the pass on the scanner and then hold it up for the agent to visually inspect it.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for X-ray screening.
  • To minimize handling during the screening process, put items such as your phone and loose change into your carry-on rather than into the bins.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA employee will need to open your bag for inspection.

Which airlines fly to Val d'Orcia?
Alitalia is a widely known carrier servicing Val d'Orcia. Search for a fare to Peretola Airport (FLR) and you'll have 121 Alitalia flights every month to choose from.
How can I find cheap tickets to Val d'Orcia?
In the last seven days, was the lowest price for a flight to Val d'Orcia. For an even cheaper fare, book ahead of time and be flexible with your travel dates. Search for your flight to Val d'Orcia, then compare prices for nearby days by clicking on our "flexible dates" link.
How much is a flight to Val d'Orcia?
You could have locked in a return airfare to Val d'Orcia from anywhere between and in the last seven days. For one-way journeys from (), the lowest amount paid during this time was just .
What are the most popular airports to fly into in Val d'Orcia?
Val d'Orcia's primary airport is Peretola Airport (FLR). Get your next thrilling adventure underway by reserving an airfare on one of the 1323 flights every month to this destination.
When is the cheapest time to fly to Val d'Orcia?
Take off to Val d'Orcia early on in the week and you'll usually be rewarded with more affordable fares. Tuesday is typically the cheapest day to hop on a plane, with Monday a close second. If you'd like to avoid the priciest flights, give Saturdays a wide berth.
How much is a plane ticket to Val d'Orcia?
Airfares ranged anywhere from to over the last seven days. When you're ready to book, we'll help you lock in a great deal to Val d'Orcia.
Which airlines with flights to Val d'Orcia employ COVID-19 cleanliness policies?
In response to the continuing pandemic, most airlines have adopted new rules and measures to help their passengers and crew take to the skies again. Here are a few examples:
  • Alitalia - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Vueling - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Ryanair - this airline is known for cleaning with disinfectant and providing passenger masks.

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.