Province of Siena Vacations & Trips from $1,035

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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 traveling on a shoestring or in the lap of luxury, Expedia are here to help you customize your next Province of Siena vacation.

Top destinations in Province of Siena

Siena featuring night scenes, landscape views and a city
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Siena

Siena

The Latest Province of Siena Vacation Packages

Price found within the past 48 hours. Click for updated prices.
La Bagnaia Golf Resort

La Bagnaia Golf Resort

5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
8.4/10 Very Good! (114 reviews)
Air conditioning an issue…..couldn’t imagine being there in middle of summer

Reviewed on Jun 14, 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (94 reviews)
Beautiful property. Excellent staff. Everyone was professional and friendly.

Reviewed on Jun 29, 2025

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (64 reviews)
Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a heads-up: if you need anything like Advil or small essentials, the nearest town is about 20 minutes away on a dirt road. Overall, everything was well done. We’d absolutely come back.

Reviewed on Jun 21, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
per person
Sep 23 - Sep 29
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Our group of three made it though challenging to find initially as located halfway down an alley. But once found the check in was easy and friendly. The room size was ok and great air conditioning. The only down side was the wifi which never came up during our 2 day stay. The elevator did go out but came back on just before check out. Friendly staff was another positive.

Reviewed on Jul 3, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 16 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Excellent Location, friendly staff and good standard room

Reviewed on Jul 1, 2025

Best Places to Vacation in Province of Siena

1. Experience Siena with a travel package

Siena, located in the heart of Tuscany, Italy, offers a rich cultural experience for visitors. The city's stunning cathedral, historical monuments, and museums provide a glimpse into its rich history. Explore the charming streets and discover beautiful churches, while enjoying the local cafes and wineries. Take part in destination activities, tours, and sightseeing to fully immerse yourself in the local atmosphere. Siena's geographic affinities make it an ideal destination for art enthusiasts and those seeking a cultural vacation. Experience the vibrant culture and history that Siena has to offer.

  • The peak season is from July to September
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Siena

2. Book your ideal San Gimignano with a vacation package

San Gimignano, located in the picturesque region of Tuscany, Italy, offers a unique cultural vacation experience. The town's historical charm is evident in its well-preserved medieval architecture, including its iconic towers. Visitors can explore numerous museums and churches, immersing themselves in the rich history and art of the area. The tranquil countryside provides the perfect backdrop for leisurely walks and wine tastings at local wineries. With its hilly landscape and stunning views, San Gimignano offers a truly immersive cultural experience that combines history, art, and the beauty of the Tuscan countryside.

  • The peak season is from November to January
  • The off-peak season is from January to March
  • Travelers tend to stay 3 days in San Gimignano

3. Enjoy Montepulciano with a travel package

Montepulciano, located in Tuscany, Italy, offers a captivating atmosphere for a cultural vacation. The town is renowned for its wineries, historical sites, and picturesque countryside. Visitors can immerse themselves in the local culture by exploring the charming streets, visiting museums and art galleries, and enjoying traditional festivals. The region is also known for its delicious cheese and offers a variety of cafes and restaurants to indulge in local cuisine. With its secluded and peaceful ambiance, Montepulciano provides a perfect setting for sightseeing, tours, and experiencing the rich cultural heritage of Tuscany.

  • The peak season is from July to September
  • The off-peak season is from January to March
  • Travelers tend to stay 3 days in Montepulciano

4. Create memories in Montalcino with a vacation package

Montalcino, located in the heart of Tuscany, Italy, offers a romantic atmosphere and experience for couples on vacation. The town is known for its picturesque wineries, where visitors can indulge in delicious wines and take in the stunning countryside views. For adventure seekers, there are opportunities for hiking and exploring the hilly terrain. History buffs will appreciate the medieval castle and monuments that dot the town. Relaxation can be found at the local spas, offering rejuvenating treatments. Montalcino also provides the perfect backdrop for romantic walks, especially during sunrise. Overall, Montalcino is a charming destination for couples seeking a romantic getaway.

  • The peak season is from March to May
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Montalcino

6. Plan your dream getaway to Castelnuovo Berardenga

Castellina in Chianti in Tuscany, Italy, offers a charming and romantic atmosphere for your vacation stay. Surrounded by rolling hills and lush countryside, this small town is perfect for a secluded and relaxing getaway. The area is renowned for its wineries, allowing you to indulge in wine tasting and explore the beautiful vineyards. You can also enjoy activities such as hiking in the nearby forests, swimming in the refreshing waters, and birdwatching. Take in the sights and immerse yourself in the local culture with destination activities, tours, and sightseeing. Castellina in Chianti is the ideal destination for a truly romantic and luxurious vacation experience.

  • The peak season is from July to September
  • The off-peak season is from November to January
  • Travelers tend to stay 3 days in Castelnuovo Berardenga

5. Find your perfect Pienza vacation

Pienza, located in the beautiful region of Tuscany, Italy, offers a charming atmosphere perfect for a cultural vacation. With its breathtaking countryside, luxury accommodations, and hilly landscapes, Pienza provides a picturesque backdrop for your visit. Immerse yourself in the rich history and architecture by exploring the town's churches, castle, and cathedral. Indulge in the local wineries and taste the exquisite wines that the region is famous for. Take in the small-town charm as you wander through the streets and admire the stunning scenery. Pienza offers a variety of destination activities, tours, and sightseeing opportunities for travelers to enjoy.

  • The peak season is from July to September
  • The off-peak season is from November to January
  • Travelers tend to stay 3 days in Pienza

Find the Best Province of Siena Vacation Packages

Best months to visit Province of Siena

Looking for the best time to visit Province of Siena? Our table will help you. Province of Siena boasts a year-round average temperature of 57.0°F, reaching a peak of 75.9°F in July, its warmest month, and dropping to an average low of 40.6°F in January, the coolest month. The annual rainfall averages 78.1mm, with November experiencing the heaviest showers, while July is the driest month.

Monthcalendar iconTemperature (Fahrenheit)temperature iconRainfallrain iconCloud coveragecloud icon
January40.6Light RainMostly Sunny
February42.8Light RainMostly Sunny
March47.5Light RainMostly Sunny
April54.0Light RainMostly Sunny
May60.4Light RainMostly Sunny
June69.8Light RainSunny
July75.9No Rain (Dry)Sunny
August75.6No Rain (Dry)Sunny
September67.1Light RainMostly Sunny
October56.8Light RainMostly Sunny
November50.2Light RainMostly Sunny
December43.3Light RainMostly Sunny

How to save money on a vacation to Province of Siena

  • Take advantage of Expedia's OneKey program to get great package deals when traveling to the Province of Siena in Tuscany, Italy.
  • Combine your flights, hotels, and car rentals with Expedia to save money and collect points.
  • Use the helpful search filters on Expedia to find the perfect accommodation within your price range.
  • Consider traveling during the off-peak season from November to January for more affordable options.
  • Utilize Expedia's price limits search filter to find a vacation package that suits your budget.
  • Explore the beautiful Province of Siena and its famous landmarks, such as Piazza del Campo and Siena Cathedral.

Province of Siena Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Fiumicino - Leonardo da Vinci Intl. Airport (FCO)
Population
42,900
Top Sights
Monte Amiata, Terme di Montepulciano Spa and Piscine Termali Theia

Province of Siena Hotel Deals

Hotel Athena
Hotel Athena
4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$143 nightly
The price is $163 total per night from Jul 30 to Jul 31
$163 total
Jul 30 - Jul 31
Total includes taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"Before we arrived the communication with the hotel was not good, but once we arrived I was stunned with how kind and helpful everyone at the hotel is. My family keeps commenting on how nice everyone is. The breakfast is very generous and delicious. The rooms are comfortable as well as the beds. I ..."

Reviewed on Jul 3, 2025

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
$433 nightly
The price is $483 total per night from Jul 10 to Jul 11
$483 total
Jul 10 - Jul 11
Total includes taxes and fees
9.2/10 Wonderful! (96 reviews)
"Beautiful property. Excellent staff. Everyone was professional and friendly."

Reviewed on Jun 29, 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Jul 9 to Jul 10
$131 total
Jul 9 - Jul 10
Total includes taxes and fees
9/10 Wonderful! (13 reviews)
"The room was very clean. The view from the room is stunning! It is very quiet and relaxing. The resort is facing Montepulciano! The staff is very nice and friendly. I highly recommend it."

Reviewed on Jun 14, 2025

Nuovo Etruria Resort
See all 6,220 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?
The cheapest Province of Siena package is $1,035, so your dream trip can become a reality --- without spending a fortune. Bundle flights, hotels, car rentals and more to create a package that's perfect for you.
How do I get a cheap travel package to Province of Siena?
If you love landing a bargain, bundle your bookings into a Province of Siena vacation package. Whether you need flights, hotels, rental cars or tours, you can book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 hotel options throughout the world to select from. Fly with who you want, check in where you like and save a packet --- now that's the ideal vacation!
Where should I stay in Province of Siena?
If you want to check out renowned sights such as Palazzo Piccolomini and Abbazia di Sant'Antimo, be sure to visit Val d'Orcia. Stay for a while to fully delve into this buzzing city.
What are the top hotels in Province of Siena?
For properties in Crete Senesi with cozy beds and friendly service, look up Hotel Athena and Palazzo Ravizza. If you're visiting San Gimignano as well, you can look forward to a solid night's sleep at Palazzo Leopoldo Dimora Storica & Spa or NH Siena.
How far in advance should I book my Province of Siena vacation?
While not all airlines advertise tickets early, customers are usually able to start comparing international flights on Expedia up to a year in advance. This is when you can nab some fantastic deals. If you're purchasing tickets last minute, you might still be in luck. Low prices sometimes become available a few weeks before departure.
What does an Expedia Province of Siena travel package include?
Flights, hotels and rental cars --- you'll find them all here. With Expedia, you can shape your Province of Siena travel package however you want. All you have to do is decide what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Province of Siena travel package?
Booking all the parts of your escape together is a great way to save. Bundle car rentals, airfares and hotels into one package. But hotels aren't your only option. Expedia features all kinds of properties, including vacation rentals like beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a Province of Siena Expedia vacation package?
You can, and with more than 550 airlines to choose from all over the world, you have plenty of choice. Look through the available options and see which airline best suits your needs and budget.
Does Expedia offer Book Now, Pay Later Province of Siena vacation packages?
If the reason for your travel has come up unexpectedly, Expedia can help take the financial strain off your shoulders. Working with online lender Affirm, we provide a Book Now, Pay Later solution for all packages. It's easy to set up a payment arrangement for your getaway that works for you.
If I'm not able to travel, can I cancel my Province of Siena vacation package?
Whether it's your flight or hotel, you can cancel and rebook it. Locked in your Province of Siena vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For older bookings, you may incur a charge from your airline, hotel or car rental company. For more details, visit our Customer Service Portal. We're here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.