Province of Siena Holidays
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Top destinations in Province of Siena
Siena
San Gimignano
Montepulciano
Pienza
Castellina in Chianti
Radda in Chianti
Top Flight + Hotel Deals in Province of Siena
Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
€1,397
per person
25 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.
Reviewed on 21 Sept 2026
Villa Tolomei Hotel & Resort
Oltrarno
€499
per person
30 Nov - 6 Dec
found 17 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (431 reviews)
Stay was excellent. Breakfast and one dinner at the Villa were very good. Only minor issue was the extender for the WiFi was not working, which limited the WiFi to only the living room and kitchen area. Still workable.
Reviewed on 12 Sept 2026
Top hotels in Province of Siena
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
€101
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (564 reviews)
"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"
Reviewed on 16 Sept 2026
Hotel Executive
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
€94
25 Oct - 26 Oct
includes taxes & fees
NH Siena
Piazza La Lizza 1 Siena SI
Fully refundableReserve now, pay when you stay
€139
25 Oct - 26 Oct
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"El hotel está fuera de las murallas de la ciudad, fuera de la zona restringida para autos, pero cerca de las atracciones de la parte histórica de la ciudad."
Reviewed on 19 Sept 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.
Frequently asked questions
How much does a Province of Siena holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Province of Siena from just €375. And the more you bundle, the more cash you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Province of Siena?
Our Province of Siena holiday packages offer plenty of savings for the savvy traveller. For the best deal, simply bundle your hotel, flights and extras (including activities) into an affordable package. But cheap prices are just the beginning of your next awesome adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels worldwide to choose from. Whatever your budget, there's a package with your name on it.
Where should I stay in Province of Siena?
Siena is an awesome city to visit. This city is where you'll find impressive sights such as Siena Cathedral and Torre del Mangia. Val dOrcia also draws in many jetsetters eager to explore some of the best attractions in Province of Siena. These include Pienza Cathedral and Palazzo Piccolomini.
What are the top hotels in Province of Siena?
Check out Hotel Athena and NH Siena. They're top picks for many travellers to Crete Senesi. If San Gimignano features in your travel itinerary, Pensione Palazzo Ravizza and Grand Hotel Continental Siena – Starhotels Collezione are two welcoming options.
How far in advance should I book my Province of Siena holiday?
Reserving your tickets early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to a year in advance. This is generally the cheapest time to book. If circumstances have left you booking late, low prices to Province of Siena occasionally appear in the weeks leading up to departure.
What does an Expedia Province of Siena travel package include?
Much of that is up to you. You can select from a variety of Province of Siena packages, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your Province of Siena trip looks like, get ready to save!
What should I know before booking a Province of Siena travel package?
A travel package can be tailored to your budget and is a terrific way to stretch your hard-earned dollars. What you include is totally up to you. Rental cars, hotels and flights — mix and match whatever combination works with your plans.
Can I choose my airline with a Province of Siena Expedia holiday package?
Yes, so take your pick! We have access to over 550 partner airlines globally, so you can customize your Province of Siena getaway according to your needs and budget.
If I'm not able to travel, can I cancel my Province of Siena holiday package?
Don't worry if you're rethinking your Province of Siena 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 totally get that life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
Stay near popular Province of Siena attractions
Piazza del Campo
9.6/10 (1,995 reviews)
Learn about the local history of Siena when you spend time at Piazza del Campo. Discover the area's beautiful countryside or seek out its local tours.
Monte Amiata
9.0/10 (100 reviews)
Explore the great outdoors at Monte Amiata, a lovely green space in Abbadia San Salvatore. Discover the area's countryside and wineries.
Siena Cathedral
9.6/10 (1,693 reviews)
Siena Cathedral is just one of the places to see in Siena, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside while you're in the area.
Pienza Cathedral
9.4/10 (460 reviews)
Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.
Tenuta Torciano Winery
9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
Castello Banfi
9.4/10 (51 reviews)
You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas or simply enjoy its wineries.
San Giovanni Terme Rapolano
9.2/10 (69 reviews)
You can take time to visit San Giovanni Terme Rapolano during your travels to Rapolano Terme. Discover the countryside and wineries in this romantic area.
Terme Antica Querciolaia
8.6/10 (8 reviews)
You can take time to visit Terme Antica Querciolaia during your travels to Rapolano Terme. Discover the countryside and wineries in this romantic area.
What to do in Province of Siena
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
€79
per adult
88% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
€49
per adult
78% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
€47
per adult
90% of travellers recommend
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
