Castiglione del Bosco Holidays from AU$3,061

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 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

Your Castiglione del Bosco Holiday

Our Castiglione del Bosco holiday packages let you customise your own adventure. Tailor your journey to suit your needs and interests and make every moment count in this fantastic city. Make your trip to Castiglione del Bosco even more fun by including some sightseeing. Tenuta Greppo Franco Biondi Santi, Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino are some of the popular attractions worth exploring. Your Castiglione del Bosco holiday is a few clicks away. Explore flights, accommodation and more on Expedia for a getaway that's tailored just for you.

The Latest Castiglione del Bosco Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
13 Sept - 19 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
I’ve had a wonderful stay at Autumn Hotel! It was very clean! The staff was amazing the room was perfect with a balcony you didn’t hear the busy noise from the street at night I will definitely book with them again! Thank you!

Reviewed on 19 Jul. 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
per person
13 Sept - 19 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Florence (FLR)
8.8/10 Excellent! (878 reviews)
Excellent location, well appointed nice rooms and spacious, good bathroom, walkable to all key places to visit in Florence, safe. Great breakfast buffet and rooftop terrace with drinks. Great gelato place right at the hotel. Location couldn't be better. Right next to Ponte Vecchio and walkable to all key attractions

Reviewed on 14 Jul. 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
per person
13 Sept - 19 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Florence (FLR)
8.6/10 Excellent! (464 reviews)
Nice hotel, very clean, a little far from main attractions, but in general I really like it

Reviewed on 14 Jul. 2025

Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
per person
13 Sept - 19 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Florence (FLR)
8.8/10 Excellent! (185 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on 22 Jun. 2025

Il Perseo

Il Perseo

3 out of 5
Historic Centre of Florence
per person
13 Sept - 19 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Florence (FLR)
9.4/10 Exceptional! (1,005 reviews)
Excellent location and friendly accomdating staff

Reviewed on 20 Jul. 2025

Castiglione del Bosco Holiday

Castiglione del Bosco Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Castello Banfi, Tenuta Greppo Franco Biondi Santi and Civic and Diocesan Museum of Sacred Art of Montalcino

Our pick of the best 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
The price is AU$2,912 per night from 5 Aug to 6 Aug
AU$2,912
5 Aug - 6 Aug
includes taxes & fees
10/10 Exceptional! (64 reviews)
"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a ..."

Reviewed on 21 Jun. 2025

Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
The price is AU$232 per night from 30 July to 31 July
AU$232
30 July - 31 July
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Great service . Location is very nice too"

Reviewed on 20 Jul. 2025

Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 20 Aug to 21 Aug
AU$211
20 Aug - 21 Aug
includes taxes & fees
8/10 Very Good! (993 reviews)
Very nice hotel
"Very nice and clean hotel. Just outside the ztl, close to historic city centre area."

Reviewed on 10 Jul. 2025

NH Siena
See all 3,252 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Discover the most popular places to visit in Castiglione del Bosco

Castello Banfi

Castello Banfi

5/5(2 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

What to do in Castiglione del Bosco

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

AU$407
per adult
100% of travellers recommend
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano
Brunello di Montalcino small-group Wine Tour

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

AU$323
per adult
100% of travellers recommend
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
small town in Italy

Brunello di Montalcino Small Group Wine Tour from Siena

AU$287
per adult
98% of travellers recommend
Brunello di Montalcino Small Group Wine Tour 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 from AU$3,061 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.