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

## 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 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 23 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

![Hotel Delle Nazioni](https://images.trvl-media.com/lodging/1000000/930000/920200/920176/dd1e8db6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Delle Nazioni

Historic Centre of Florence

$1,784

per person

Jun 2 - Jun 5

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Florence (FLR)

8.6/10 Excellent! (1,014 reviews)

Location!! We took trains almost every day and this hotel is right across the street from the station. There was no noise from the trains or busy street while trying to sleep. Staff was very helpful and breakfast was good every day. Hotel is clean and always felt safe late at night. Walkable to tourist spots and Oltrarno. It was a perfect choice for us!

Reviewed on Mar 13, 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/2026-04-18/2026-04-25/?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

$1,133 nightly

$1,258 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&regionId=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

$109 nightly

$126 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&selected=1110843&PinnedHotelID=1110843&HadPinnedHotel=true&regionId=3000028417)

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/5eddd92b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

 Palazzo Ravizza

Pian dei Mantellini 34 Siena SI

Fully refundableReserve now, pay when you stay

$111 nightly

$128 total

Mar 22 - Mar 23

Total with taxes and fees

9.4/10 Exceptional! (762 reviews)

Beautiful building. Clean and safe. Great breakfast buffet. Everything is in walking distance to hotel. One front desk staff member was not polite or welcoming but overall it was a lovely stay.

Reviewed on Mar 17, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=1760168&PinnedHotelID=1760168&HadPinnedHotel=true&regionId=3000028417)

[See all 3,274 properties in Castiglione del Bosco](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&regionId=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) |

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## 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.