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
Top Province of Siena Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Grand Hotel Cavour
Historic Centre of Florence
CA $1,709
per person
Nov 8 - Nov 14
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !
Reviewed on Sep 15, 2026
Aurum Firenze
Historic Centre of Florence
CA $1,846
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Brilliant location, no more than 15-20 maximum minutes to walk to all the main sites. The staff worked hard and were very friendly and helpful.
Reviewed on Sep 17, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $3,795
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Excellent staff. Extremely helpful. Booked reservations for us and always happy to help. Hotel is nice and well maintained. Room was spacious for Italy. Shower was only tight squeeze
Reviewed on Sep 18, 2026
Hotel Duomo Firenze
Historic Centre of Florence
CA $1,775
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
I can’t understand how the property even considers selling a room the size I was in under a staircase with a shower which barely trickles.
Reviewed on Sep 19, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $2,634
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
I would say this is a 3.5 star property. The room was clean but basic, same for the bathroom and amenities like soap etc. the location is very central but the room was still quiet. There is no concierge and the staff was not able to make any reservations for us.
Reviewed on Sep 19, 2026
Province of Siena Hotel Deals
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
CA $141
CA $168 total
Oct 6 - Oct 7
includes taxes & fees
9.4/10 Exceptional! (564 reviews)
"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"
Reviewed on Sep 16, 2026
Hotel Executive
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
CA $111
CA $130 total
Oct 12 - Oct 13
includes taxes & fees
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
CA $328
CA $369 total
Oct 20 - Oct 21
includes taxes & fees
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 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 $1,709. 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
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.
Monte Amiata
9.0/10 (100 reviews)
Explore the great outdoors at Monte Amiata, a lovely green space in Abbadia San Salvatore. Discover the area's countryside and wineries.
Siena Cathedral
9.6/10 (1,693 reviews)
Siena Cathedral is just one of the places to see in Siena, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside while you're in the area.
Pienza Cathedral
9.4/10 (460 reviews)
Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.
Piazza Grande
9.4/10 (125 reviews)
You can find out about the history of Montepulciano with a visit to Piazza Grande. While you're here, you can savor the wineries.
Tenuta Torciano Winery
9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
Castello Banfi
9.4/10 (51 reviews)
You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas, or simply enjoy its wineries.
Terme Antica Querciolaia
8.6/10 (8 reviews)
You can take time to visit Terme Antica Querciolaia during your travels to Rapolano Terme. Discover the countryside and wineries in this romantic area.
What to do in Province of Siena
Chianti Half Day Wine Tour from Florence
CA $36
per adult
88% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $79
per adult
78% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $115
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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- Beautiful apartment for 4 guests with pool
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- Hotels near Palazzo Pubblico
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- Hotel Duomo
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- Podere la casa
- Flights from Taverne d'Arbia
- Flights from Ottawa (YOW) to Siena (SAY)
- Flights from Calgary (YYC) to Siena (SAY)
- Flights from Montreal (YUL) to Siena (SAY)
- Flights from Toronto (YYZ) to Siena (SAY)
- Flights to Siena
- Flights to Province of Siena
- Flights from London (LHR) to Siena (SAY)
- Flights from Siena
- Flights from Vancouver (YVR) to Siena (SAY)
- Visit San Giovanni A Cerreto
- Visit Orgia
- Church of San Sigismondo
- Visit Monteroni d'Arbia
- Visit Siena Historical Center
- Cappella di Piazza
- Visit Siena City Centre
- Buondonno Winery
- Le Miccine
- Visit Ville di Corsano
- Visit Province of Siena
- Visit Monteriggioni
- Fortezza Medicea
- Visit San Prospero
- Rosia Vacations
- Casa Vinicola Luigi Cecchi
- Visit Siena
- Siena Vacations
- Visit Villa A Sesta
- Visit Badesse
- Dollar Rent A Car Rental Cars in Siena
- Sports Car Car Rentals in Siena
- Car rental Siena
- Car rental Monteriggioni
- Locauto Rental Cars in Siena
- Hertz Rental Cars in Siena
- Enterprise Rental Cars in Siena
- National Car Rental Rental Cars in Siena
- Alamo Rent A Car Rental Cars in Siena
- Budget Rental Cars in Siena
- Van Car Rentals in Siena
- Convertible Car Rentals in Siena
- Goldcar rental Rental Cars in Siena
- Europcar Rental Cars in Siena
- Ok Mobility Rental Cars in Siena
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
