Province of Siena Vacations & Trips from ￥251,686

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Top destinations in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.

Siena

Siena
A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

San Gimignano

San Gimignano
A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

Montalcino

Montalcino

The Latest Province of Siena Vacation Packages

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

Aurum Firenze

Historic Centre of Florence
￥251,686
per person
Nov 11 - Nov 18
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
￥270,346
per person
Nov 12 - Nov 19
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (584 reviews)
All the staff were amazing and helpful! The kitchen staff for breakfast catered for all out needs. The spa was excellent too and I’d highly recommended this hotel to anyone. It’s in a Great location with good links to the airport and tourist spots across the city.

Reviewed on Aug 29, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
￥301,676
per person
Nov 11 - Nov 18
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
￥254,936
per person
Nov 11 - Nov 18
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
excellent location, clean and staff helpful

Reviewed on Aug 23, 2026

Bernini Palace

Bernini Palace

Historic Centre of Florence
￥313,474
per person
Nov 11 - Nov 18
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.8/10 Exceptional! (1,012 reviews)

Province of Siena Hotel Deals

La Certosa di Pontignano

La Certosa di Pontignano

loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
￥15,820
￥18,886 total
Sep 6 - Sep 7
includes taxes & fees
9.4/10 Exceptional! (559 reviews)
"Beautiful place, very quiet, in love with gardens"

Reviewed on Aug 31, 2026

La Certosa di Pontignano
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
￥93,963
￥104,472 total
Sep 30 - Oct 1
includes taxes & fees
9.6/10 Exceptional! (165 reviews)
"Fantastic stay!"

Reviewed on Aug 30, 2026

Precise Tale Poggio Alla Sala
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
￥35,575
￥40,059 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Le personnel est très serviable que ça soit pour le stationnement au restaurant ou à la réception un service impeccable. La terrasse a une belle vue panoramique et un menu à se lécher les doigts."

Reviewed on Aug 30, 2026

Hotel Athena
See all 6,212 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.

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 ￥251,686. 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
A historic building with a tower, a fountain, and a courtyard.

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.
See properties
A grand cathedral with intricate Gothic architecture, a prominent bell tower, and a bustling square with people.

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.
See properties
A historic church with a bell tower, arched windows, and a central dome.

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.
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A historic building with a statue in front.

Banca Monte dei Paschi di Siena

8.6/10 (116 reviews)
You can learn about the history of Siena when you stop by Banca Monte dei Paschi di Siena. Discover the beautiful countryside while you're in the area.
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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.
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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.
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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.
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What to do in Province of Siena

Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

￥9,570
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

￥17,299
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

￥4,601
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
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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.