Province of Siena Vacations & Trips from $1,077

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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

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The Latest Province of Siena Vacation Packages

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Air conditioner was excellent!!!

Reviewed on Aug 11, 2025

Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World

Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World

5 out of 5
Save 100% on your flight
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (421 reviews)
Absolutely enjoyed everything about Terme di Saturnia and will be back!

Reviewed on Aug 4, 2025

Albergo Le Terme

Albergo Le Terme

4 out of 5
per person
Nov 5 - Nov 10
found 13 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9/10 Wonderful! (65 reviews)
We enjoyed our stay in this hotel with friendly staff and decent facilities. However, the place could benefit from some upgrading. Our room was lacking in proper maintenance as the fan in the bathroom was very noisy, and worst of all the internet and cell service was extremely slow.

Reviewed on Apr 13, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great location and very clean

Reviewed on Aug 12, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 1 - Oct 6
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 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

Province of Siena Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$153 nightly
The price is $174 total per night from Aug 23 to Aug 24
$174 total
Aug 23 - Aug 24
Total includes taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Amazing staff and phenomenal food and views"

Reviewed on Aug 12, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $139 total per night from Aug 18 to Aug 19
$139 total
Aug 18 - Aug 19
Total includes taxes and fees
9.2/10 Wonderful! (686 reviews)
Just beautiful
"The building, the views, the staff, the food, everything was just incredible. It was so quiet we felt like we were the only people there until we went for breakfast and realised there were others in the hotel. The view from the our room at the back of the hotel over the Tuscan hills will live with ..."

Reviewed on Aug 9, 2025

Palazzo Ravizza
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
$430 nightly
The price is $485 total per night from Aug 25 to Aug 26
$485 total
Aug 25 - Aug 26
Total includes taxes and fees
9.4/10 Exceptional! (243 reviews)
"Beautiful hotal located in such a paradise location amazing view very good food. The staff was very nice. The service was amazing. I definitely recommend the place. It’s a beautiful relaxing, gorgeous."

Reviewed on Aug 13, 2025

Castello di Spaltenna- Small Luxury Hotels of the World
See all 6,249 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 $1,077, 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.