Castiglione del Bosco Vacations from $966

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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, Fortress of Montalcino and Museum of Brunello 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.
Alfieri9

Alfieri9

3 out of 5
Historic Centre of Florence
Price was $1,245, price is now $966 per person
$966
per person
Jan 11 - Jan 18
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (175 reviews)

Hotel Berchielli

Hotel Berchielli

4 out of 5
Historic Centre of Florence
Price was $1,672, price is now $1,258 per person
$1,258
per person
Jan 19 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
breakfast helpful staff

Reviewed on Oct 23, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,539, price is now $1,194 per person
$1,194
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location, very clean and beautiful views. Staff was very kind and helpful

Reviewed on Oct 28, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $1,458, price is now $1,134 per person
$1,134
per person
Dec 8 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
We loved the rooftop bar. Spectacular. Staff was very helpful and friendly. WiFi was quite slow. Room was good. Toiletries were good. Great location.

Reviewed on Oct 29, 2026

Palazzo Lorenzo Hotel Boutique & Spa

Palazzo Lorenzo Hotel Boutique & Spa

4 out of 5
San Lorenzo
Price was $1,253, price is now $981 per person
$981
per person
Dec 4 - Dec 10
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (626 reviews)

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Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

9.6/10 (5 reviews)
You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.
See properties

What to do in Castiglione del Bosco

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$28
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$51
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

$39
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
See all activities in Castiglione del Bosco

Castiglione del Bosco Hotel Deals

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
$1,264 nightly
The price is $1,401 total per night from Nov 4 to Nov 5
$1,401 total
Nov 4 - Nov 5
Total with taxes and fees
10/10 Exceptional! (87 reviews)
"Unique property well maintained and quite Serene , great staff"

Reviewed on Oct 30, 2026

Castiglion del Bosco, A Rosewood Hotel
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $95 total per night from Nov 30 to Dec 1
$95 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” ..."

Reviewed on Oct 29, 2026

Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $331 total per night from Nov 30 to Dec 1
$331 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (644 reviews)
"Great stay!"

Reviewed on Oct 29, 2026

Grand Hotel Continental Siena – Starhotels Collezione
See all 3,361 properties in Castiglione del Bosco
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, Tenuta Greppo Franco Biondi Santi and Capanna of Cencioni

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Frequently asked questions

How much does a Castiglione del Bosco vacation package cost?
Offering excellent value package deals from $966 on Expedia, you'll be thrilled with how little a vacation to Castiglione del Bosco costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Castiglione del Bosco?
February, March and November are great times to search for cheap Castiglione del Bosco vacation packages. Traveling in quieter months means you can typically find lower prices on flights and accommodations.
How many days is enough for Castiglione del Bosco?
Generally, a handful of days is enough to visit the top attractions during your Castiglione del Bosco vacation. But if you want to have time to relax or go on day trips, think about extending your itinerary.
How to find the best Castiglione del Bosco package deals?
Use Expedia's filters to find some of the best Castiglione del Bosco package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Castiglione del Bosco package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Castiglione del Bosco vacation as a package?
You can enjoy significant savings on your Castiglione del Bosco retreat by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Castiglione del Bosco?
If you're considering an impromptu Castiglione del Bosco getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking ahead.
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: 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 with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Castiglione del Bosco vacation packages?
Set off on your perfect escape to Castiglione del Bosco with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until the next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.