Province of Siena Holidays

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Top destinations in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.

Siena

Siena
A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

San Gimignano

San Gimignano
A hillside town with historic buildings and a prominent church.

Montepulciano

Montepulciano
A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti

Castellina in Chianti
A narrow street with stone buildings, a 'Zona traffico limitato' sign, and people walking.

Radda in Chianti

Radda in Chianti

Our pick of the best Province of Siena Hotel Deals

La Certosa di Pontignano

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
NZ$210
6 Oct - 7 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

La Certosa di Pontignano
Hotel Executive

Hotel Executive

Via Nazareno Orlandi 32 Siena SI
NZ$200
12 Oct - 13 Oct
includes taxes & fees
Hotel Executive
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
NZ$466
20 Oct - 21 Oct
includes taxes & fees
Hotel Athena
See all 6,182 properties in Province of Siena
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 . 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

A historic square with cobblestone pavement, surrounded by multi-story buildings with traditional architecture.

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.
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A historic building with a tower, a fountain, and a courtyard.

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.
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A grand cathedral with intricate Gothic architecture, a prominent bell tower, and a bustling square with people.

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.
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A historic church with a bell tower, arched windows, and a central dome.

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.
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A stone lion sculpture on a building facade.

Piazza Grande

9.4/10 (125 reviews)
You can find out about the history of Montepulciano with a trip to Piazza Grande. While you're here, you can savour the wineries.
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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.
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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.
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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.
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What to do in Province of Siena

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

NZ$139
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

NZ$43
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting

NZ$91
per adult
90% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
See all activities in Province of Siena

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