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

A historic town with tightly packed buildings, a prominent tower, and a church.
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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 $2,621, price is now CA $1,688 per person
CA $1,688
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The location of this hotel is fantastic and central to all the major sights. We were able to walk to every major landmark between 4-10 minutes. The staff were lovely and hard working. The AC, shower/hot water worked great. The breakfast was a typical continental style and I found it satisfactory to a hotel this size. The one thing that was challenging was getting a regular wifi signal. Overall, great stay for a family of 4.

Reviewed on Jul 24, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $7,301, price is now CA $4,397 per person
CA $4,397
per person
Aug 30 - Sep 5
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (151 reviews)
Magical location, pools, staff, property.

Reviewed on Jul 19, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,651, price is now CA $1,701 per person
CA $1,701
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.4/10 Good! (1,011 reviews)
The front staff were great, my issue was with their corporate office. O had originally booked 2 nights, 2 rooms for 4 people. I realized I had made an error the next day. I should have have booked 3 nights, 2 rooms, for 4 people. I canceled and rebooked. As a novice traveller I did not realize this apparently was not the way to fix my error. I tried to get a refund for the original booking, and had to go through expedia. Expedia said the hotel would not answer their multiple attempts to contact. I ended paying double for 2 nights and lost $800. Lesson learned the hard way.

Reviewed on Jul 27, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $3,278, price is now CA $2,198 per person
CA $2,198
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
8.6/10 Excellent! (493 reviews)
Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on Jun 26, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was CA $3,298, price is now CA $2,276 per person
CA $2,276
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
i don't like the hotel has a small bathroom . everything is close to restaurants and stuff

Reviewed on Jul 26, 2026

Province of Siena Hotel Deals

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $482 per night from Aug 27 to Aug 28
CA $482
CA $546 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (620 reviews)
"What a wonderful stay right in the cent of siena historic district. really recommend this hotel. Staff are very kind and welcoming."

Reviewed on Jul 25, 2026

Grand Hotel Continental Siena – Starhotels Collezione
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 $846 per night from Aug 9 to Aug 10
CA $846
CA $940 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (155 reviews)
"Magical location, pools, staff, property."

Reviewed on Jul 19, 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 CA $663 per night from Aug 2 to Aug 3
CA $663
CA $745 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (217 reviews)
"The AC didn’t work well."

Reviewed on Jul 23, 2026

Borgo Scopeto Wine & Country Relais
See all 6,193 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 $1,688. 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.

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 take a trip to Piazza del Campo. Discover the area's beautiful countryside, or seek out its local tours.
See properties

What to do in Province of Siena

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

CA $29
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

CA $105
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

CA $80
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
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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.