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.
Hotiday Room Collection - Rapallo

Hotiday Room Collection - Rapallo

4 out of 5
per person
2 Oct - 5 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Pisa (PSA)
No reviews
Hotel Blu di Te

Hotel Blu di Te

4 out of 5
per person
2 Oct - 5 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Pisa (PSA)
9.6/10 Exceptional! (205 reviews)
Really enjoyed our time at the hotel. The staff was fantastic and took a personal interest in us. Highly recommended!!

Reviewed on 21 May 2025

Hotel Piccolo Portofino

Hotel Piccolo Portofino

4 out of 5
Save 100% on your flight
per person
2 Oct - 5 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Pisa (PSA)
9/10 Wonderful! (563 reviews)
Everything is excellent except that the bathroom ventilation needs to improve to eliminate the bad smell.

Reviewed on 4 Jul 2025

Grand Hotel Miramare

Grand Hotel Miramare

5 out of 5
Save 100% on your flight
per person
2 Oct - 5 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Pisa (PSA)
9.6/10 Exceptional! (528 reviews)
Beautiful property, stylish and comfortable rooms, gorgeous views and the amenities were great. Piano player in the evening was a highlight and so was the beach. Highly recommend.

Reviewed on 9 Jul 2025

Grand Hotel Bristol Spa Resort - by R Collection Hotels

Grand Hotel Bristol Spa Resort - by R Collection Hotels

5 out of 5
per person
2 Oct - 5 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Pisa (PSA)
9/10 Wonderful! (887 reviews)
Excellent stay. We loved the hotel and the staff were wonderful.

Reviewed on 1 Jul 2025

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 €1,630 per night from 5 Aug to 6 Aug
€1,630
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 €130 per night from 30 Jul to 31 Jul
€130
30 Jul - 31 Jul
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"We had a good time, only issue was isolation, last night we had trouble sleeping because of our noisy neighbor"

Reviewed on 12 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 €118 per night from 20 Aug to 21 Aug
€118
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 3,255 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

San Giovanni d'Asso Station

You can take time to visit San Giovanni d'Asso Station during your travels to San Giovanni d'Asso. Discover the area's countryside and spas.

San Giovanni d'Asso Station

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

€229
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

€180
per adult
100% of travellers recommend
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Val d'Orcia Full Day Tour with Wine Tasting from Florence

Val d'Orcia Full Day Tour with Wine Tasting from Florence

€238
per adult
Val d'Orcia Full Day Tour with Wine Tasting from Florence
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 €555 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.