Castiglione del Bosco Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Castiglione del Bosco

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
The price is S$2,845 per night from 12 Aug to 13 Aug
S$2,845
12 Aug - 13 Aug
includes taxes & fees
10/10 Exceptional! (65 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 3 Aug, 2025

Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
The price is S$222 per night from 23 Aug to 24 Aug
S$222
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Beautiful location overlooking the hills of Tuscany! Right from Martina checking us in, and the beautiful room with views, everything was amazing! Very clean rooms and comfortable bed. Very nice bathroom and all the amenities. We enjoyed the breakfast each morning, nice selection of food to choose ..."

Reviewed on 3 Aug, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 24 Aug to 25 Aug
S$179
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (683 reviews)
"Breakfast with amazing view on the terrace. Fresh homemade bread, butter, coffee and we with my sister were in love with the spinach pie. To be honest, we were very upset stay short time in this beautiful place and decided comeback for longer time. We were sleep as a baby, good quality linen, towels ..."

Reviewed on 6 Aug, 2025

Palazzo Ravizza
See all 3,264 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.

Popular places to visit

Abbazia di Sant'Antimo

5/5(1 review)

You can learn about the history of Castelnuovo dell'Abate with a visit to Abbazia di Sant'Antimo. Visit the area's spas or simply enjoy its wineries.

Abbazia di Sant'Antimo

What to do in Castiglione del Bosco

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

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

S$172
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

S$38
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Brunello di Montalcino small-group Wine Tour

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

S$271
per adult
100% of travellers recommend
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
See all activities in Castiglione del Bosco

Frequently asked questions

How much does a Castiglione del Bosco holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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?
To score cheap Castiglione del Bosco holiday packages, plan your getaway outside of busy periods such as school holidays. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Castiglione del Bosco?
Typically, a handful of days is enough to visit the main sights during your Castiglione del Bosco holiday. However, if you prefer to have some time to kick back or take day trips, think about extending your trip.
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 holiday package well in advance.
Is it cheaper to book a Castiglione del Bosco holiday as a package?
You can enjoy significant savings on your Castiglione del Bosco retreat by booking a personalised holiday 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 holiday 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 the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Castiglione del Bosco.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to put aside for your trip to Castiglione del Bosco. Then, pick a property that matches your budget, whether that's a low-cost stay or a high-end retreat.
  3. Decide how long to go away for: Now that you're up to speed on Castiglione del Bosco, you can work out the right length of your holiday. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your accommodation and airfare: Once you've settled on your dates and duration, book the right Castiglione del Bosco holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.