Castiglione del Bosco Holidays

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Top Flight + Hotel Deals in Castiglione del Bosco

Price found within the past 48 hours. Click for updated prices.
LHP Certaldo Resort

LHP Certaldo Resort

5 out of 5
Save 100% on your flight
Price was €1,012, price is now €600 per person
€600
per person
30 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (532 reviews)
nice property

Reviewed on 30 Jun 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €1,872, price is now €983 per person
€983
per person
30 Sept - 6 Oct
found 1 day ago
Return direct flight included
Knock (NOC) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Good service and the room was clean

Reviewed on 10 Jul 2026

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
Price was €1,385, price is now €803 per person
€803
per person
30 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (415 reviews)
Wonderful property, amazing hosts. 20 minutes outside of Florence center-easy to get a taxi. My family loved everything about our stay here!

Reviewed on 7 Jul 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was €4,030, price is now €2,465 per person
€2,465
per person
30 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (290 reviews)
Best staff. The breakfast was phenomenal. The spa surreal. The sunset view unreal.

Reviewed on 11 Jul 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was €2,482, price is now €1,548 per person
€1,548
per person
30 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)

Top hotels in Castiglione del Bosco

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
The price is €2,173 per night from 31 Jul to 1 Aug
€2,173
31 Jul - 1 Aug
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
The price is €340 per night from 10 Aug to 11 Aug
€340
10 Aug - 11 Aug
includes taxes & fees
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is €163 per night from 6 Aug to 7 Aug
€163
6 Aug - 7 Aug
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful rooms, we had one with the terrace and a view. Very quiet. Gorgeous rooftop restaurant, easy parking. 10 min walk to the square."

Reviewed on 9 Jul 2026

Hotel Athena
See all 3,360 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.

Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

9.6/10 (5 reviews)
You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.
See properties

What to do in Castiglione del Bosco

Montepulciano Gran Tour

Montepulciano Gran Tour

€15
per adult
Montepulciano Gran Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

€94
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montalcino, Pienza & Montepulciano Wine & Food Tour

Val d’Orcia Wine Tour with Lunch & Brunello

€119
per adult
84% of travellers recommend
Val d’Orcia Wine Tour with Lunch & Brunello
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 €600 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.