Holiday rentals near Castiglion del Bosco Winery
We found 2,296 holiday rentals — enter your dates for availability
If you'd like to stay close to Castiglion del Bosco Winery, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Castiglion del Bosco Winery
Showing deals for:14 Nov - 21 Nov
Image gallery for Winery Villa in the heart of Nobile Vineyards.
10 out of 10 rating
Exceptional
(14 reviews)
Winery Villa in the heart of Nobile Vineyards.
Montepulciano, Toscana
9% off
Price is NZ$6,347
NZ$907 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Castiglion del Bosco Winery
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Sleeps 12 · 6 bedrooms · 8+ bathrooms
10 out of 10
exceptional
(12 reviews)
Top rated rentals - Castiglion del Bosco Winery
Secret Val D’Orcia
10 out of 10
exceptional
(18 reviews)
We have stayed in the Val D’Orcia before - it’s an area we love, but this was really next level.Privacy, huge beautiful grounds and amazing views from every window!Wonderful hosts who went out of their way to make this the most special stay - thank you, it was amazing!
Vernon H.
Stayed May 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value