Castiglione del Bosco Vacations from $779

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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 Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,155, price is now $779 per person
$779
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
We were able to check-in early. It is walkable from Santa Maria Novella train station and so are the points of interest. When we arrived, the electric metal blinds was not working. Letitia gave us a sheet to temporarily give us privacy. When we came back from our tour the next day, it was already fixed. Great place to stay. Worth the money we paid for. Santa Maria Novella Basilica is close by. Worth visiting. Well recommended.

Reviewed on Oct 19, 2025

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,314, price is now $2,356 per person
$2,356
per person
Dec 6 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (297 reviews)
The hotel was very nice however there was construction below us. Additionally, the restaurant and bar were not open due to renovations.

Reviewed on Mar 5, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $4,454, price is now $3,170 per person
$3,170
per person
Dec 6 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (3 reviews)
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,423, price is now $1,741 per person
$1,741
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
This is a beautiful hotel.It is spotlessly clean.The staff are friendly and helpful. Breakfast exceeded our expectations. The choice of food and service were excellent. It’s a good location to see the sights and get to the train station to visit Pissa etc. We will definitely book here for our next visit.

Reviewed on Oct 11, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,063, price is now $1,486 per person
$1,486
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
Very small room and shower without door.not even place to put a chair

Reviewed on Oct 16, 2025

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Discover the most popular places to visit in Castiglione del Bosco

CastelloBanfi Il Borgo, Luxury Retreat in Montalcino Italy Growing up as a devoted history lover, I have always daydreamed about living in a castle. I used to recreate that magical word in my phantasy, populated with vassals and fortune tellers, with dames and cavaliers. This summer, my stay at the beautiful Tuscan resort CastelloBanfi Il Borgo in Montalcino, Italy gave me the chance to turn this dream into reality. Ambra Castello Banfi 2 This beautiful property is set in an ancient stone hamlet that was built in the 1700 sunder the protective walls of the 13th Century Castle “Castelloalle Mura”. What was once used as a dwelling for farmers who toiled with their noble landowners has today been restyled into the luxurious rooms and suites of this jewel of Tuscan hospitality. Ambra Castello Banfi While the architectural style remained unchanged and very authentic, the interior was renovated with modern comforts, premium fabrics and exclusive accessories. Luxury Retreat in Montalcino Ambra Castello cannon dream of living in a castle We were so lucky to stay in one of their exclusive 14 rooms, surrounded by history, vineyards and olive groves. CastelloBanfiilBorgo is truly a place of peace and serenity.Enjoying breakfast or “aperitivo” at sunset from the infinity pool that over looks immense stretches of Brunello vines is simply good for the soul. Castello well Ambra Castello But wait until you witness the most delectable gastronomic experience at “Taverna”, one of the two epic restaurants on property. That’s the ultimate experience to please all of your senses! Ambra tee at Castello Ambra Castello pool Ambra in a castle In the next post will show you all the delicious Italian food we got to savor at the castle’s restaurant, but for now enjoy some beautiful photos and the video about this incredible resort! CastelloBanfiIlBorgo Ambra in Montalcino Italy

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
Poggio Antico winery- Brunello is the best!!

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

$52
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
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

$104
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
See all activities in Castiglione del Bosco

Castiglione del Bosco Hotel Deals

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
$1,234 nightly
The price is $1,369 total per night from Nov 14 to Nov 15
$1,369 total
Nov 14 - Nov 15
Total with taxes and fees
10/10 Exceptional! (67 reviews)
"Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal."

Reviewed on Aug 3, 2025

Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $110 total per night from Nov 12 to Nov 13
$110 total
Nov 12 - Nov 13
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"We loved that the hotel was on the edge of Siena, but just inside the city wall, so that we could drive right up to the hotel and park but then walk easily anywhere in the city. The hotel itself was lovely, with fantastic staff and excellent breakfast. Our room was clean, very comfortable, with nice ..."

Reviewed on Oct 16, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $113 total per night from Nov 5 to Nov 6
$113 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (729 reviews)
"We enjoyed our stay here."

Reviewed on Oct 18, 2025

Palazzo Ravizza
See all 3,260 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.

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 $779 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.