Title: Castiglione del Bosco Vacation Packages 2026 from $1,409 | Expedia.com [Castiglione del Bosco Travel Guide](https://expedia.com/Castiglione-Del-Bosco.dx3000028417)[Hotels in Castiglione del Bosco](https://expedia.com/Castiglione-Del-Bosco-Hotels.d3000028417.Travel-Guide-Hotels)[Vacation Rentals in Castiglione del Bosco](https://expedia.com/Castiglione-Del-Bosco-Vacation-Rentals.d3000028417.Travel-Guide-VacationRentals)[Flights to Castiglione del Bosco](https://expedia.com/Cheap-Flights-To-Castiglione-Del-Bosco.d3000028417.Travel-Guide-Flights)[Things to do in Castiglione del Bosco](https://expedia.com/Things-To-Do-In-Castiglione-Del-Bosco.d3000028417.Travel-Guide-Activities)[Car Rentals in Castiglione del Bosco](https://expedia.com/Car-Rentals-In-Castiglione-Del-Bosco.d3000028417.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6025631/4982164e-5dfb-4949-8519-f2f14021eed9.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Castiglione del Bosco Vacations from $1,409 ## Book a Hotel + Flight or Car together to unlock savings Photo by tom owens - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Castiglione del Bosco Vacation Take the guesswork out of travel planning with a Castiglione del Bosco vacation package. A great neighborhood to stay in this vibrant city is Poggioferro, which is great for views and much more. Like to start exploring your surroundings? [Tenuta Greppo Franco Biondi Santi](https://www.expedia.com/Tenuta-Greppo-Franco-Biondi-Santi-Montalcino.d6103260.Vacation-Attraction), [Fortress of Montalcino](https://www.expedia.com/Fortress-Of-Montalcino-Montalcino.d553248621533000896.Vacation-Attraction) and [Museum of Brunello](https://www.expedia.com/Museum-Of-Brunello-Montalcino.d553248621533000897.Vacation-Attraction) are among the top places to visit during your trip to Castiglione del Bosco. That dream Castiglione del Bosco vacation is just clicks away. Search flights, accommodations and more on Expedia for an adventure that's tailored just for you. ## The Latest Castiglione del Bosco 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 $1,409 per person May 21 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 7.6/10 Good! (1,008 reviews) It's clearly a block of flats that has been converted to a hotel. My room was a bit cramped but for a few nights, I could live with it. There is a slight smell which in high summer is likely to be prominent. If you don't expect a 5 star experience, then it's OK. My room was clean, the staff friendly enough and walking distance to all the major sights. If I was back in Florence, would I stay there again, probably not, but I've no real complaints. Just don't expect too much and you'll be fine. Reviewed on Mar 16, 2026 ![Hotel La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/d1c916cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel La Scaletta Al Ponte Vecchio Historic Centre of Florence Save 100% on your flight $2,767 per person May 8 - May 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 8.8/10 Excellent! (971 reviews) There were no Vineyard views but it is in a decent location in Florence. The "Garden Suite" is a joke. It overlooks a courtyard that was covered in green moss and had a hose strewed about. It was not usable. So there was no view of anything. We opened the window overlooking it at night to get some air and I assume this is why we woke up with lots of bites! We never saw a mosquito though. They told us the AC didn't work. The hotel's elevator is a 1 person elevator that was too scary to use really. Our room was on the seventh floor. The staff did help with bringing the luggage up but if you don't like to climb MANY stairs, this is not the place for you. We tried to upgrade to a third person and this caused quite the comotion and really I feel they charged us in excess by making us upgrade to a suite and then charged more per person. They blamed a communication error but that was really not it! One desk person tried to make it right and was very nice but really in the end fell short. The suite was spacious and nice but the glass shelf in it had not been dusted in quite some time. It had a soaking tub, steam room and sauna, although the sauna and steam room did not work. The rooftop bar has a nice view but it is a workout to get up there! It's also where they serve breakfast and where the workout room is. I would not recommend this hotel. Reviewed on Mar 17, 2026 ![Maxim Axial](https://images.trvl-media.com/lodging/3000000/2540000/2532900/2532899/b9927c89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maxim Axial Historic Centre of Florence Save 100% on your flight $1,973 per person May 8 - May 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 8.6/10 Excellent! (1,005 reviews) Great location and wonderful room! Will book again! Reviewed on Mar 6, 2026 ![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/89ed1f8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Duomo Firenze Historic Centre of Florence $2,057 per person Jun 2 - Jun 5 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Florence (FLR) 9.2/10 Wonderful! (1,002 reviews) We loved staying here for our first visit to Florence.. perfect location , warm & friendly staff , lovely room with balcony & comfy bed as well as a fantastic breakfast… Hopefully will return! X Reviewed on Mar 8, 2026 ![Hotel Berchielli](https://images.trvl-media.com/lodging/1000000/530000/521300/521260/3061994d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Berchielli Historic Centre of Florence $2,319 per person May 24 - May 29 found 20 hours ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 9.4/10 Exceptional! (1,001 reviews) Very good Breakfast with many food options. Great service ! Reviewed on Jan 21, 2026 Don't see what you're looking for? See all available trips from Columbus to Castiglione del Bosco [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-17/2026-04-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=GRS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Castiglione del Bosco #### Castello Banfi 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. [](https://expedia.com/Castello-Banfi-Montalcino.d6103264.Vacation-Attraction) #### Tenuta Greppo Franco Biondi Santi You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas. [](https://expedia.com/Tenuta-Greppo-Franco-Biondi-Santi-Montalcino.d6103260.Vacation-Attraction) #### Castiglion del Bosco Winery You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco. [](https://expedia.com/Castiglion-Del-Bosco-Winery-Montalcino.d828039750155694080.Vacation-Attraction) ### What to do in Castiglione del Bosco ![Montalcino: Guided Winery Tour and Wine Tasting](https://mediaim.expedia.com/localexpert/44628122/e1c18867-816c-4ff5-aaae-8b2f08187f9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montalcino: Guided Winery Tour and Wine Tasting $53 per adult [](https://expedia.com/things-to-do/montalcino-guided-winery-tour-and-wine-tasting.a44628122.activity-details) ![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano Wine Tasting in the Tuscan Countryside $29 per adult [](https://expedia.com/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details) ![Seggiano: Guided Tour of the Olive Grove and Food Tasting](https://mediaim.expedia.com/localexpert/48314154/3c3e6332-4460-423d-8ee4-7953fc5d8637.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Seggiano: Guided Tour of the Olive Grove and Food Tasting $29 per adult [](https://expedia.com/things-to-do/seggiano-guided-tour-of-the-olive-grove-and-food-tasting.a48314154.activity-details) [See all activities in Castiglione del Bosco](https://expedia.com/things-to-do/search?rid=3000028417) ## Castiglione del Bosco Hotel Deals ![Castiglion del Bosco, A Rosewood Hotel](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/fd17fc16_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Castiglion del Bosco, A Rosewood Hotel Localita Castiglion del Bosco Montalcino SI Fully refundableReserve now, pay when you stay $1,129 nightly $1,253 total Mar 21 - Mar 22 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=3%2F21%2F2026&endDate=3%2F22%2F2026&selected=2173539&PinnedHotelID=2173539&HadPinnedHotel=true®ionId=3000028417) ![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/e92eb5d8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Athena P Mascagni 55 Siena SI Fully refundableReserve now, pay when you stay $119 nightly $137 total Mar 18 - Mar 19 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) Excellent repeat stay. Top-notch staff, beautiful views and rooms, excellent breakfast and on-site dinner restaurant. Reviewed on Mar 7, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F18%2F2026&endDate=3%2F19%2F2026&selected=866580&PinnedHotelID=866580&HadPinnedHotel=true®ionId=3000028417) ![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/f43eb5fd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Chiusarelli Viale Curtatone 15 Siena SI Fully refundableReserve now, pay when you stay $107 nightly $124 total Mar 18 - Mar 19 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=3%2F18%2F2026&endDate=3%2F19%2F2026&selected=1110843&PinnedHotelID=1110843&HadPinnedHotel=true®ionId=3000028417) [See all 3,274 properties in Castiglione del Bosco](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F18%2F2026&endDate=3%2F19%2F2026®ionId=3000028417) 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. ## Find the Best Castiglione del Bosco Vacation Packages ## Castiglione del Bosco Essential Information | Language | Italian | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | Euros | | Local Welcome | Ciao | | Local Goodbye | Ciao | | Max Temp Winter | 50ºF | | Max Temp Summer | 85ºF | | Top Sights | [Castello Banfi](https://www.expedia.com/Castello-Banfi-Montalcino.d6103264.Vacation-Attraction), [Tenuta Greppo Franco Biondi Santi](https://www.expedia.com/Tenuta-Greppo-Franco-Biondi-Santi-Montalcino.d6103260.Vacation-Attraction) and [Capanna of Cencioni](https://www.expedia.com/Capanna-Of-Cencioni-Montalcino.d553248635976265059.Vacation-Attraction) | ## More vacations you might like ![](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) 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![](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 Castiglione del Bosco vacation package cost? ### What are the cheapest months to go to Castiglione del Bosco? ### How many days is enough for Castiglione del Bosco? ### How to find the best Castiglione del Bosco package deals? ### Is it cheaper to book a Castiglione del Bosco vacation as a package? ### When to book a vacation package to Castiglione del Bosco? ### How to plan a trip to Castiglione del Bosco? > 1. Choose when to go: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Castiglione del Bosco. > 2. Plan your budget wisely: In addition to the cost of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that could arise during your trip to Castiglione del Bosco. > 3. Organize your Castiglione del Bosco getaway with Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning): Look for and book accommodations and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Castiglione del Bosco together. > 4. Decide how long to go away for: Now that you know more about Castiglione del Bosco, you can work out the right length of your break. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list. > 5. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Castiglione del Bosco vacation package. > 6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Castiglione del Bosco's highlights. Find all the fun [things to do in Castiglione del Bosco](https://www.expedia.com/Things-To-Do-In-Castiglione-Del-Bosco.d3000028417.Travel-Guide-Activities) with our dedicated activity guide. ### Does Expedia offer Book Now, Pay Later Castiglione del Bosco vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app