Title: Province of Siena Vacation Packages 2026 from $956 | Expedia.com [Province of Siena Travel Guide](https://expedia.com/Province-Of-Siena.dx6047850)[Province of Siena Hotels](https://expedia.com/Destinations-In-Province-Of-Siena.d6047850.Hotel-Destinations)[Vacation Rentals in Province of Siena](https://expedia.com/Destinations-In-Province-Of-Siena.d6047850.Vacation-Rental-Destinations)[Province of Siena Flights](https://expedia.com/Destinations-In-Province-Of-Siena.d6047850.Flight-Destinations)[Car Rentals in Province of Siena](https://expedia.com/Destinations-In-Province-Of-Siena.d6047850.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/9821/884960f6-e87c-438b-a2f2-88d51116ab26.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Province of Siena Vacations & Trips from $956 ## Book a Hotel + Flight or Car together to unlock savings ### 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](https://www.expedia.com/Siena.d9821.Destination-Travel-Guides) at Monteriggioni Castle and Palazzo Pubblico — two leading attractions here. Another city worth adding to your itinerary is [Montepulciano](https://www.expedia.com/Montepulciano.d601351.Destination-Travel-Guides). 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 ![San Gimignano featuring street scenes and shopping as well as a large group of people](https://images.trvl-media.com/place/11091/d03de615-2cbf-4c14-9fbd-54622308a833.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### San Gimignano [](https://expedia.com/San-Gimignano.d11091.Destination-Travel-Guides) ![Siena featuring night scenes, landscape views and a city](https://images.trvl-media.com/place/9821/307db1c5-e88f-4f43-9c03-4cb0c895dce7.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Siena [](https://expedia.com/Siena.d9821.Destination-Travel-Guides) ![Montepulciano showing landscape views, a city and heritage architecture](https://images.trvl-media.com/place/601351/8e058793-a90b-4fbe-bc1c-fe0b632a5e96.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Montepulciano [](https://expedia.com/Montepulciano.d601351.Destination-Travel-Guides) ![Montalcino showing a sunset and heritage architecture](https://images.trvl-media.com/place/6025631/a4fff669-7ab2-4916-b5e4-83b0ec3a76bf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Montalcino [](https://expedia.com/Montalcino.d6025631.Destination-Travel-Guides) ![Pienza showing a small town or village, a monument and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Pienza [](https://expedia.com/Pienza.d6023645.Destination-Travel-Guides) ![Castellina in Chianti which includes a church or cathedral, religious elements and heritage architecture](https://images.trvl-media.com/place/55534/68deebc9-9310-492d-8f83-85d906ba54aa.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Castellina in Chianti [](https://expedia.com/Castellina-In-Chianti.d55534.Destination-Travel-Guides) ![Gaiole in Chianti vineyards and panorama at sunset. Tuscany, Italy](https://images.trvl-media.com/place/6034141/742742ec-2351-4570-b774-e482e8359ccf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Castelnuovo Berardenga [](https://expedia.com/Castelnuovo-Berardenga.d6034141.Destination-Travel-Guides) ![San Quirico d\'Orcia featuring heritage architecture](https://images.trvl-media.com/place/602606/7d9c0730-c1fd-40a2-b524-d6d103f44783.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### San Quirico d'Orcia [](https://expedia.com/San-Quirico-DOrcia.d602606.Destination-Travel-Guides) ![View over the hills from the Brolio Castle](https://images.trvl-media.com/place/603149/c6d3b602-5ecb-46fa-8174-b38eecda296b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Gaiole in Chianti [](https://expedia.com/Gaiole-In-Chianti.d603149.Destination-Travel-Guides) ## The Latest Province of Siena Vacation Packages Price found within the past 48 hours. Click for updated prices. ![Aurum Firenze](https://images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/3c6602ae_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Firenze Historic Centre of Florence Save 100% on your flight $956 per person Apr 25 - Apr 28 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 7.6/10 Good! (1,002 reviews) It was near the train and next to awesome places. The view if you get a balcony is so cute and peaceful Reviewed on Feb 28, 2026 ![Aurum Uffizi](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/4fb74083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Uffizi Historic Centre of Florence $1,403 per person Apr 22 - Apr 26 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 7.6/10 Good! (1,000 reviews) Smaller room then expected and shower did flood the floor so not the best of showers. Bed very comfortable Nice friendly & helpful staff and perfect location to explore the city. Reviewed on Feb 22, 2026 ![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/50470bbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Cavour Historic Centre of Florence Save 100% on your flight $3,162 per person Apr 30 - May 4 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 9.2/10 Wonderful! (1,002 reviews) Great hotel near the center. Walking distance to everything. I enjoyed the quality of the hotel and the roof top bar was amazing. Good service. Rooms were a little small but not sure if that was because of my budget or whether the hotel rooms were just smaller due to the type/age of the building. All in all I would recommend and most of your time is spent outdoors anyway. Reviewed on Mar 3, 2026 ![Hotel Donatello](https://images.trvl-media.com/lodging/2000000/1200000/1192400/1192329/b82709a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Donatello Historic Centre of Florence $1,322 per person Apr 27 - May 1 found 1 day ago Roundtrip non-stop flight included San Francisco (SFO) to Florence (FLR) 7.4/10 Good! (465 reviews) Beautiful breakfast buffet. Great location to walking to all the beautiful sights. Would stay again!! Reviewed on Oct 2, 2025 ![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dcb50280_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Castiglione Save 100% on your flight $1,025 per person Apr 14 - Apr 23 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Florence (FLR) 8.6/10 Excellent! (261 reviews) Nice and cute place. Great price. Reviewed on Oct 27, 2025 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6047850) ## Best Places to Vacation in Province of Siena ## 1\. Experience [Siena](https://www.expedia.com/Siena.d9821.Destination-Travel-Guides) 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](https://www.expedia.com/San-Gimignano.d11091.Destination-Travel-Guides) 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](https://www.expedia.com/Montepulciano.d601351.Destination-Travel-Guides) 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](https://www.expedia.com/Montalcino.d6025631.Destination-Travel-Guides) 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](https://www.expedia.com/Castelnuovo-Berardenga.d6034141.Destination-Travel-Guides) 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](https://www.expedia.com/Pienza.d6023645.Destination-Travel-Guides) 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 ## 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](https://www.expedia.com/Monte-Amiata-Abbadia-San-Salvatore.d6183371.Vacation-Attraction), [Terme di Montepulciano Spa](https://www.expedia.com/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction) and [Piscine Termali Theia](https://www.expedia.com/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction) | ## Province of Siena Hotel Deals ![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Athena P Mascagni 55 Siena SI Fully refundableReserve now, pay when you stay $120 nightly $138 total Mar 9 - Mar 10 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) Clea Reviewed on Feb 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=866580&PinnedHotelID=866580&HadPinnedHotel=true®ionId=6047850) ![NH Siena](https://images.trvl-media.com/lodging/1000000/20000/15800/15716/9d41d91a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### NH Siena Piazza La Lizza 1 Siena SI Fully refundableReserve now, pay when you stay $99 nightly $115 total Mar 22 - Mar 23 Total with taxes and fees 8.2/10 Very Good! (1,001 reviews) Nicely central. Reviewed on Feb 12, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=15716&PinnedHotelID=15716&HadPinnedHotel=true®ionId=6047850) ![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Hotel Continental Siena – Starhotels Collezione Banchi Di Sopra 85 Siena SI Fully refundableReserve now, pay when you stay $323 nightly $367 total Mar 18 - Mar 19 Total with taxes and fees 9.2/10 Wonderful! (584 reviews) The best hotel in siena for sure, thank you! Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F18%2F2026&endDate=3%2F19%2F2026&selected=796662&PinnedHotelID=796662&HadPinnedHotel=true®ionId=6047850) [See all 6,098 properties in Province of Siena](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F5%2F2026&endDate=3%2F6%2F2026®ionId=6047850) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf 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[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Province of Siena vacation package cost? ### How do I get a cheap travel package to Province of Siena? ### Where should I stay in Province of Siena? ### What are the top hotels in Province of Siena? ### How far in advance should I book my Province of Siena vacation? ### What does an Expedia Province of Siena travel package include? ### What should I know before booking a Province of Siena travel package? ### Can I choose my airline with a Province of Siena Expedia vacation package? ### Does Expedia offer Book Now, Pay Later Province of Siena vacation packages? ### If I'm not able to travel, can I cancel my Province of Siena vacation package? Explore a world of travel with Expedia ## Other vacations you might like - Top cities in Province of Siena - Vacations and getaways similar to Province of Siena - Best vacation destinations by month - Expedia's Latest Trends - [Siena Vacations ](https://expedia.com/Siena.d9821.Destination-Travel-Guides) - [San Gimignano Vacations ](https://expedia.com/San-Gimignano.d11091.Destination-Travel-Guides) - [Montepulciano Vacations ](https://expedia.com/Montepulciano.d601351.Destination-Travel-Guides) - [Montalcino Vacations ](https://expedia.com/Montalcino.d6025631.Destination-Travel-Guides) - [Pienza Vacations ](https://expedia.com/Pienza.d6023645.Destination-Travel-Guides) - [Castellina in Chianti Vacations ](https://expedia.com/Castellina-In-Chianti.d55534.Destination-Travel-Guides) - [Castelnuovo Berardenga Vacations ](https://expedia.com/Castelnuovo-Berardenga.d6034141.Destination-Travel-Guides) - [Gaiole in Chianti Vacations ](https://expedia.com/Gaiole-In-Chianti.d603149.Destination-Travel-Guides) - [San Quirico d'Orcia Vacations ](https://expedia.com/San-Quirico-DOrcia.d602606.Destination-Travel-Guides) - [Radda in Chianti Vacations ](https://expedia.com/Radda-In-Chianti.d601693.Destination-Travel-Guides) - [Monteriggioni Vacations ](https://expedia.com/Monteriggioni.d5722.Destination-Travel-Guides) - [Poggibonsi Vacations ](https://expedia.com/Poggibonsi.d4964.Destination-Travel-Guides) - [Liguria Vacations ](https://expedia.com/Liguria.d6048740.Destination-Travel-Guides) - [Emilia-Romagna Vacations ](https://expedia.com/Emilia-Romagna.d6048673.Destination-Travel-Guides) - [Umbria Vacations ](https://expedia.com/Umbria.d6048668.Destination-Travel-Guides) - [Lazio Vacations ](https://expedia.com/Lazio.d6048637.Destination-Travel-Guides) - [Marche Vacations ](https://expedia.com/Marche.d6048667.Destination-Travel-Guides) - [January Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-january) - [February Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-february) - [March Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-march) - [April Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-april) - [May Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-may) - [June Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-june) - [July Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-july) - [August Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-august) - [September Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-september) - [October Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-october) - [November Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-november) - [December Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-december) ### Expedia's Latest Trends Hotels - [Luxury Hotels in Province of Grosseto](https://expedia.com/Destinations-In-Province-Of-Grosseto-Luxury-Hotel.0-0-d6047854-tLuxuryHotel.Hotel-Filter-Destinations) - 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