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

San Gimignano

San Gimignano

Top Province of Siena Vacation Deals

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,346, price is now CA $1,681 per person
CA $1,681
per person
Jul 5 - Jul 10
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Our room was very small. The bathroom was very tight. The breakfast was so so. We had so much better.our other hotel in Venice. The breakfast room is tight and not much in pastries

Reviewed on May 1, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,423, price is now CA $1,709 per person
CA $1,709
per person
Jul 5 - Jul 10
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Excellent helpful staff let us store our bags in the lobby for a couple of hours after checkout- much appreciated- clean and quiet - central location was walkable to everywhere- and they were very nice to our 6 month old baby

Reviewed on May 2, 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Price was CA $3,248, price is now CA $2,303 per person
CA $2,303
per person
Jun 10 - Jun 16
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (266 reviews)
Incredible place. History, attention to details, ambiance, food - just perfection!

Reviewed on May 3, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $2,934, price is now CA $2,150 per person
CA $2,150
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (485 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

Maxim Axial

Maxim Axial

3 out of 5
Historic Centre of Florence
Price was CA $2,943, price is now CA $2,157 per person
CA $2,157
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (1,006 reviews)
This hotel is in the center of Florence. You are able to get to all destinations by foot. If you have a rental car, you actually have to pull up in front and they will pick up the car and valet it for you. The only downside is my room didn’t have any air-conditioning so it was a little hot and stuffy at night besides that I would definitely stay here again.

Reviewed on Apr 30, 2026

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 $303 per night from Jun 3 to Jun 4
CA $303
CA $341 total
Jun 3 - Jun 4
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Great breakfast, clean room and onsite parking a huge plus. The staff was very friendly and helpful. The only downsides was the staff provided a recommendation for a restaurant that was not good and our room was located right outside of the reception area, which was a bit noisy during busy times ...

Reviewed on May 1, 2026

Hotel Athena
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 CA $620 per night from May 12 to May 13
CA $620
CA $692 total
May 12 - May 13
includes taxes & fees
9.4/10 Exceptional! (131 reviews)
Absolutely amazing! We travel with small children and this accomodation was incredible. The accomodation and staff was 5 star

Reviewed on May 3, 2026

Precise Tale Poggio Alla Sala
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from May 17 to May 18
CA $288
CA $325 total
May 17 - May 18
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Clean rooms and central location

Reviewed on Apr 29, 2026

NH Siena
See all 6,097 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.
All Inclusive Vacations
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Beach Vacations
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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 $1,681. 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.