Province of Siena Vacation Packages

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Your Province of Siena Vacation

Lock in a vacation package to Province of Siena and enjoy what it means to travel on your own terms. You'll be impressed by its walking trails, nature and views. With so many things to explore on a trip to Province of Siena, it can be tricky to know where to begin. Kick off your travels in Siena at Monteriggioni Castle and Palazzo Pubblico — two leading attractions here. Another city worth adding to your itinerary is Montepulciano. Be sure not to miss Val di Chiana and Piazza Grande. Whether you're travelling on a shoestring or in the lap of luxury, Expedia are here to help you customize your next Province of Siena vacation.

Top vacation destinations in Province of Siena

FlightsFlightsHotelsHotels

Siena

Siena

Top Province of Siena Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $3,199, price is now CA $1,888 per person
CA $1,888
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $3,890, price is now CA $2,374 per person
CA $2,374
per person
May 15 - May 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Super clean room, modern, good shower and bed, nice and quiet, 10 minutes from the train station, breakfast was done in time slots and was ok maybe could have had more selection, staff were friendly, my only bugbear was the WiFi was really slow and i ended up using my hot-spot instead

Reviewed on Apr 12, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $4,050, price is now CA $2,750 per person
CA $2,750
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (483 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $7,961, price is now CA $5,595 per person
CA $5,595
per person
Jun 4 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!

Reviewed on Apr 5, 2026

Bob W Florence Santa Croce

Bob W Florence Santa Croce

3 out of 5
Historic Centre of Florence
Price was CA $4,379, price is now CA $3,119 per person
CA $3,119
per person
Jun 4 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.8/10 Excellent! (3 reviews)

Province of Siena Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Apr 16 to Apr 17
CA $266
CA $300 total
Apr 16 - Apr 17
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
Walkable to town center. Comfy beds and spotless rooms. Front desk is delightful and helpful. Excellent breakfasts that you will miss later :)

Reviewed on Apr 5, 2026

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Apr 27 to Apr 28
CA $275
CA $310 total
Apr 27 - Apr 28
includes taxes & fees
9.4/10 Exceptional! (776 reviews)
Excellent location. Less than 15 minute walk to major attractions. Numerous restaurants close by.

Reviewed on Apr 9, 2026

Palazzo Ravizza
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Apr 20 to Apr 21
CA $199
CA $227 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Pretty basic stay, the bed was very hard and the pillows thin. Breakfast was generous in portions and okay given the accommodations. Staff was helpful and kind, including when we had a problem with the heating.

Reviewed on Apr 7, 2026

Hotel Chiusarelli
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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.
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Frequently asked questions

How much does a Province of Siena vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Province of Siena from just CA $1,888. 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 vacation packages offer plenty of savings for the savvy traveler. 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 travelers 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 vacation?
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 vacation 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 vacation package?
Don't worry if you're rethinking your Province of Siena vacation 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.

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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.