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 Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,621, price is now CA $1,484 per person
CA $1,484
per person
Nov 10 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Right near the attractions. Easy to get around

Reviewed on Sep. 4, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,961, price is now CA $1,612 per person
CA $1,612
per person
Nov 10 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Good value for price and location.

Reviewed on Sep. 8, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was CA $3,646, price is now CA $2,151 per person
CA $2,151
per person
Nov 10 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (470 reviews)
We never had an opportunity to use the spa

Reviewed on Sep. 8, 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was CA $3,574, price is now CA $2,274 per person
CA $2,274
per person
Nov 10 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
8.8/10 Excellent! (907 reviews)
Loved this hotel so much…will be back!!!

Reviewed on Sep. 8, 2025

Collegio alla Querce - Auberge Collection

Collegio alla Querce - Auberge Collection

5 out of 5
Le Cure
Price was CA $6,995, price is now CA $4,462 per person
CA $4,462
per person
Nov 2 - Nov 8
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Florence (FLR)
10/10 Exceptional! (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 $300 per night from Oct 6 to Oct 7
CA $300
CA $338 total
Oct 6 - Oct 7
includes taxes & fees
Hotel Athena
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 CA $623 per night from Sep 15 to Sep 16
CA $623
CA $702 total
Sep 15 - Sep 16
includes taxes & fees
Borgo Scopeto Wine & Country Relais
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Sep 14 to Sep 15
CA $166
CA $193 total
Sep 14 - Sep 15
includes taxes & fees
Hotel Relais II Chiostro di Pienza
See all 6,275 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.
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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 $1,484. 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.