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.
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Siena

Siena

Top hotels in Province of Siena

Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 13 Jul to 14 Jul
S$149
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very good! (543 reviews)
"Nice clean hotel. Breakfast ok. Good parking"

Reviewed on 6 Jul, 2026

Hotel Executive
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 S$794 per night from 5 Aug to 6 Aug
S$794
5 Aug - 6 Aug
includes taxes & fees
9.6/10 Exceptional! (148 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on 19 Jun, 2026

Precise Tale Poggio Alla Sala
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
The price is S$709 per night from 13 Jul to 14 Jul
S$709
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (210 reviews)
"Absolutely wonderful stay. The onsite restaurant was amazing and the staff was very attentive and helpful. There are nice wineries and restaurants nearby too and the concierge made very helpful recommendations and reservations for us. Use the hotel name (and not just the address) since the Apple ..."

Reviewed on 8 Jul, 2026

Borgo Scopeto Wine & Country Relais
See all 6,216 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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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

S$117
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

S$207
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

S$129
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
See all activities in Province of Siena

* 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.