Castiglione del Bosco Vacations from $646

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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.
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $939, price is now $646 per person
$646
per person
Jan 14 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (474 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,350, price is now $916 per person
$916
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
15.6/10 Exceptional! (1,000 reviews)
Room was spotless and very nice English speaking staff. Very good breakfast!

Reviewed on Nov 18, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,928, price is now $1,998 per person
$1,998
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Florence (FLR)
19.6/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 2025

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

4 out of 5
Price was $937, price is now $653 per person
$653
per person
Jan 14 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
18.4/10 Exceptional! (175 reviews)
The property is beautifully old but be careful how much luggage you bring as there is no elevator, Only stairs. Room is nice. Bathrooms nicely updated. No complaints!

Reviewed on Sep 30, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,248, price is now $877 per person
$877
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
15.2/10 Exceptional! (1,002 reviews)
Convenient location to fast food and train station

Reviewed on Nov 7, 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

4/5(6 reviews)

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

5/5(5 reviews)

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
Olive Oil Tours and Tasting at Frantoio di Montalcino

Olive Oil Tours and Tasting at Frantoio di Montalcino

$58
per adult
Olive Oil Tours and Tasting at Frantoio di Montalcino
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
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
Fully refundableReserve now, pay when you stay
$1,249 nightly
The price is $1,385 total per night from Nov 30 to Dec 1
$1,385 total
Nov 30 - Dec 1
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
$81 nightly
The price is $93 total per night from Dec 9 to Dec 10
$93 total
Dec 9 - Dec 10
Total with taxes and fees
9.2/10 Wonderful! (999 reviews)
La ubicación es genial, el personal es muy amable y la habitación está impecable.

Reviewed on Nov 8, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Dec 2 to Dec 3
$105 total
Dec 2 - Dec 3
Total with taxes and fees
9.2/10 Wonderful! (740 reviews)
Very welcoming and attentive staff. Breakfast was amazing. I didn’t expect the gorgeous views!

Reviewed on Nov 4, 2025

Palazzo Ravizza
See all 3,243 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 $646 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.