Val d'Orcia Holidays
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Top Flight + Hotel Deals in Val d'Orcia
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
€389
per person
17 Jan - 23 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
We had a wonderful stay here. Only two nights, but the hotel was exactly what we needed!
Reviewed on 25 Oct 2026
Maxim Axial
Historic Centre of Florence
€490
per person
17 Jan - 23 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (1,009 reviews)
Great location, good breakfast, however the room did not look like the one in the pictures.
Reviewed on 26 Oct 2026
The Social Hub Florence Belfiore
Santa Maria Novella
€439
per person
17 Jan - 23 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (757 reviews)
Unbelievably great hotel.... Modern , new, fresh....the room was very modern and clean....the rooftop is a huge huge space with portions open to the public and separate pool area for guests only....spectacular views from the rooftop....the poolside lounge beds for
two was very relaxing..the pool is a long architectural masterpiece...the hotel has so many special lounges for guests only where you can relax .....the hotel is located right next to the tram train that takes you directly to the train station and all the downtown areas....the hotel has security 24-7 monitoring who goes up the elevators...
Reviewed on 26 Oct 2026
Top hotels in Val d'Orcia
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
€1,252
4 Nov - 5 Nov
includes taxes & fees
10/10 Exceptional! (86 reviews)
"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."
Reviewed on 23 Oct 2026
Corte Francigena - Apartments
Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
€127
1 Nov - 2 Nov
includes taxes & fees
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
€565
15 Nov - 16 Nov
includes taxes & fees
9/10 Wonderful! (380 reviews)
"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The ..."
Reviewed on 23 Oct 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.
Stay near popular Val d'Orcia attractions
Pienza Cathedral
9.4/10 (460 reviews)
Pope Pius II's Renaissance masterpiece showcases harmonious Gothic elements and luminous three-nave design. Arrive early to admire the 15th-century Sienese paintings and enjoy panoramic Tuscan views from the corridor.
Historic Centre of Pienza
9.6/10 (42 reviews)
Pienza's Historic Centre showcases Pope Pius II's Renaissance ideal city vision with harmonious architecture. Explore cobblestone streets, the Cathedral and Palazzo Piccolomini, and sample the town's famous pecorino cheese.
Castello Banfi
9.4/10 (51 reviews)
This medieval estate blends Tuscan tradition with world-renowned winemaking excellence. Sample award-winning Brunello di Montalcino while overlooking rolling vineyards from the restored 18th-century village.
Tenuta Greppo Franco Biondi Santi
8.6/10 (8 reviews)
Birthplace of Italy's prestigious Brunello di Montalcino wine, Tenuta Greppo has defined excellence since 1888. Tour the historic cellars and vineyards where the Biondi-Santi family's winemaking traditions thrive.
Fortress of Montalcino
9.2/10 (54 reviews)
This pentagonal medieval stronghold was the final bastion of Siena's resistance against Medici conquest. Climb its historic ramparts for panoramic Tuscan views before sampling Brunello wines at the fortress enoteca.
Castiglion del Bosco Winery
9.6/10 (5 reviews)
This historic estate, a founding consortium member, produces Italy's finest Brunello di Montalcino wines. Tour the vineyard and cellars before savouring wine pairings with local cheeses amid the Tuscan countryside.
Abbazia di Sant'Antimo
9.6/10 (111 reviews)
This medieval Romanesque abbey offers a serene glimpse into monastic life amid Tuscan olive groves. Explore the intricate stone carvings and listen for occasional Gregorian chants echoing through its ancient walls.
Palazzo Piccolomini
9.4/10 (199 reviews)
This Renaissance masterpiece was Pope Pius II's summer residence, designed by Bernardo Rossellino. From its hanging gardens, savour breathtaking panoramic views across the Val d'Orcia's rolling Tuscan landscape.
What to do in Val d'Orcia
Val d’Orcia Wine Tour with Lunch & Brunello
€119
per adult
84% of travellers recommend
Brunello di Montalcino Premium Wine Tour from Siena
€119
per adult
76% of travellers recommend
Montalcino: Brunello Wine Tasting with Tuscan Specialities
€69
per adult
Frequently asked questions
How much does a Val dOrcia holiday package cost?
Our Val dOrcia holiday packages, which start from as low as €389, are the easiest way to save big bucks. Select your favourite flights, hotels and rental cars to create a personalized escape.
How do I get a cheap travel package to Val dOrcia?
Just imagine all the fun things you could do in Val dOrcia with a wad of extra cash in your pocket. Watch your savings stack up when you bundle your flights, hotels and extras into a Val dOrcia holiday package. You have loads of choice with Expedia too. In fact, you can pick from over 550 airlines and 1,000,000 hotel options throughout the world. Whether you're enjoying a break with the family or adventuring alone, planning a getaway to Val dOrcia is better with a package.
Where should I stay in Val dOrcia?
It makes sense to stay near the action. Many visitors like to book hotels around top attractions, like Pienza Cathedral, Palazzo Piccolomini and Abbazia di SantAntimo.
What are the top hotels in Val dOrcia?
Rosewood Castiglion del Bosco in the Tavernelle neighbourhood is a wonderful choice for a Val dOrcia holiday. Book a room here and you'll be well-placed to get out and discover all that this dynamic city has to offer.
How far in advance should I book my Val dOrcia holiday?
While prices do change, we generally recommend booking your flight as soon as possible. Most international airfares can be found on Expedia up to 12 months in advance. If circumstances have left you booking late, you might still be lucky. Cheap tickets to Val dOrcia occasionally appear only weeks before departure.
What does an Expedia Val dOrcia travel package include?
Expedia has all you need to lock in Val dOrcia escape, but what your package looks like is up to you. Pick from any combination of flights, rental cars and hotels. In search of some activities or tours to keep you busy? Once you've made your booking, you can add them on too. No matter your style or budget, there's a holiday package to match your needs.
What should I know before booking a Val dOrcia travel package?
Our prices are already low. However, you'll grab even more bargains when you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and a terrific range of choice.
Can I choose my airline with a Val dOrcia Expedia holiday package?
Yes, and with more than 550 airlines to pick from worldwide, you're not short on choice. Scroll through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Val dOrcia holiday package?
Don't stress if you're rethinking your Val dOrcia holiday package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We get that your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.
Explore a world of travel with Expedia
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- Flights to Bagni San Filippo
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- Flights to Montalcino
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- Flights from Torrita di Siena
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- Flights from Piancastagnaio
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- Amorosa Holidays
- Visit Arcidosso
- Visit Brunello di Montalcino Wine Area
- Cantina Contucci
- Cantina del Redi
- Visit Chiusure
- Church of Our Lady of the Snows
- Church of St. Agnes
- Fonteverde Terme
- Mining Museum Park
- Montepulciano Holidays
- Visit Montepulciano
- Palazzo Avignonesi
- Parco Piscine Capenti Outdoor Pool
- Visit Piancastagnaio
- Piazza Italia
- Pienza Cathedral
- San Giovanni d'Asso Station
- Visit San Giovanni d'Asso
- Visit Sant'Albino
- Visit Seggiano
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
