Castiglione del Bosco Vacations from $1,259

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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.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,820, price is now $1,259 per person
$1,259
per person
Aug 9 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Clean and long lasting hot water for shower!

Reviewed on May 30, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $5,228, price is now $3,246 per person
$3,246
per person
Jul 6 - Jul 12
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (135 reviews)
Beautiful stay for our honeymoon. This is definitely a place to go and feel at peace in the Tuscan countryside. 15 min away from some wineries and 20 min away from Montepulciano. Great balance of feeling relaxed by the spa and pool with some quick getaways. Lastly, the restaurant was beyond excellent. Expensive but well worth it.

Reviewed on May 23, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,691, price is now $2,304 per person
$2,304
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (63 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

Park Hotel Villa Ariston

Park Hotel Villa Ariston

4 out of 5
Price was $3,449, price is now $2,338 per person
$2,338
per person
Jul 6 - Jul 12
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.8/10 Excellent! (131 reviews)
Highly recommend the Park Villa Ariston! The property is very clean and the staff are amazing. High praise for the breakfast and pool. We hope to return soon

Reviewed on May 14, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,344, price is now $2,327 per person
$2,327
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (18 reviews)
Outstanding hotel and a remarkable experience staying there. The room was large and beautifully decorated as the rest of the hotel. Service was impeccable and friendly. Food was great. Lovely and intimate atmosphere. Attention to details and distinctive effort to attend to our needs. The hotel manager and Lavinia at the front desk stood out, but everybody else was extremely helpful. I hope to return!

Reviewed on Nov 14, 2025

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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.

Castello Banfi

Fortress of Montalcino

Find out about the history of Montalcino with a stop at Fortress of Montalcino. Visit the area's spas, or simply enjoy its wineries.

Fortress of Montalcino

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.

Tenuta Greppo Franco Biondi Santi

What to do in Castiglione del Bosco

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$53
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

$59
per adult
Montalcino: Renowned Tuscan Olive Oil Mill Tour & 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
$2,213 nightly
The price is $2,446 total per night from Jun 7 to Jun 8
$2,446 total
Jun 7 - Jun 8
Total with taxes and fees
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
$200 nightly
The price is $226 total per night from Jun 28 to Jun 29
$226 total
Jun 28 - Jun 29
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Location is good. Large property with good parking. Staff is very helpful and friendly. The hotel aesthetic is bland and utilitarian. Breakfast is good. The rooftop deck is lovely but small."

Reviewed on May 26, 2026

Hotel Athena
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $95 total per night from Jun 7 to Jun 8
$95 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (538 reviews)
"excellent breakfast and very clean"

Reviewed on Apr 27, 2026

Hotel Executive
See all 3,299 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 $1,259 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.