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Check prices for these dates

In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Villas in Castiglione del Bosco

Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (83)
"The villa is huge and well appointed with anything you could imagine There are two large dining rooms inside and several well appointed outside patio areas. The bucolic setting includes birds , roaming sheep down the hill meandering from field to field. Couldn’t be more restful! Also close enough to Siena , San gimingnano Assisi for day trips and even Florence Will definitely return. "
Villa in Montalcino, exclusive for you, stunning view!!!
Winery Villa in the heart of Nobile Vineyards.
Outdoor dining

Winery Villa in the heart of Nobile Vineyards.

10.0 out of 10, Exceptional, (14)
"We love our stay. House and property are beautiful."
Winery Villa in the heart of Nobile Vineyards.
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (90)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Outdoor dining

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (103)
"Property was fantastic, easily accommodated our group of 9 people. Francesca took very good care of us, arranging wine tours, dinners at the house and a cooking class which we thoroughly enjoyed. I highly recommend this place"
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Stunning Villa: 24 guests, private SwimmingPool
Exterior

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (29)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool
Stunning private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking
Exterior

Stunning private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking

9.8 out of 10, Exceptional, (29)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Stunning private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (54)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
The price is SAR 517
SAR 605 total
includes taxes & fees
12 Sep - 13 Sep
Il Poggio dell'Eremita
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Outdoor pool

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

10.0 out of 10, Exceptional, (54)
"The views from this charming villa, the beautifully manicured grounds, the outdoor eating space, made our stay fantastic. The living area and kitchen were comfortable and functional. Bedrooms are not super bright but opening the shutters during the day helps immensely and each room has a great view! Luigi was very friendly and responsive. Would 100% book this place again. "
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Charming Villa with private pool between Pienza and Montepulciano
Exterior

Charming Villa with private pool between Pienza and Montepulciano

10.0 out of 10, Exceptional, (47)
"I have rented many villas and this stay was up there among the best. Wonderful villa, everything was clean and worked properly and I can’t emphasize enough how great the location was. When you stay there go to Casa Newton for cocktails, beautiful boutique hotel a six minute drive away. "
Charming Villa with private pool between Pienza and Montepulciano
Villa with unique view of Siena with private pool
Property grounds

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Outdoor pool, a heated pool

WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool

10.0 out of 10, Exceptional, (50)
"We loved our stay. The Villa was gorgeous and Gaia was very responsive to any questions we had."
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Holiday house with private garden and pool in a typical Tuscan hamlet.
Outdoor dining

Holiday house with private garden and pool in a typical Tuscan hamlet.

10.0 out of 10, Exceptional, (4)
"We had such a great time here! The house is beautiful, with a large and closed garden where our dog could run freely. The pool was stunning and gave us many relaxing moments under the Tuscan sun. We felt immediately welcome. Upon arrival we were warmly greeted by the host and toasted together to a great holiday. During our stay, any questions we had were answered quickly and kindly. A place to look back on and hopefully to return to one day!"
Holiday house with private garden and pool in a typical Tuscan hamlet.
Villa Larniano, With Private Pool And View On Vineyard
Outdoor dining

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (65)
"Our stay was absolutely delightful. The house is perched atop a hill, offering sweeping views of the surrounding vineyards—pure Tuscan magic. There’s plenty of outdoor seating to soak in the scenery, and the spacious porch made the perfect setting for unforgettable family dinners while watching the sunset. The kitchen is exceptionally well-equipped, ideal for preparing large, home-cooked meals to share with loved ones. Check-in was seamless, and communication with the owner via WhatsApp was...
Villa Larniano, With Private Pool And View On Vineyard
Montepulciano Luxe Escape
Outdoor dining

Montepulciano Luxe Escape

Montepulciano Luxe Escape
XIII Century Tower with Private Panoramic Pool
Exterior

XIII Century Tower with Private Panoramic Pool

XIII Century Tower with Private Panoramic Pool
Le Colombelline 12, Emma Villas
Exterior

Le Colombelline 12, Emma Villas

Le Colombelline 12, Emma Villas
BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Terrace/patio

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino
Property grounds

Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino

Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Outdoor dining

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

9.0 out of 10, Wonderful, (4)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Villa luna with pool and garden near the center of Siena
Property grounds

Villa luna with pool and garden near the center of Siena

9.0 out of 10, Wonderful, (27)
"We had a great time "
Villa luna with pool and garden near the center of Siena
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.
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Top Castiglione del Bosco Hotel Reviews

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Frequently asked questions

How much do villas in Castiglione del Bosco cost?
Rates for villas in Castiglione del Bosco range between SAR 517 and SAR 517 per night. Whatever your budget, you can find a place that fits the bill on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Castiglione del Bosco?
Pack your suitcase and pick from 594 villas in Castiglione del Bosco. For a family escape, a getaway with pals and everything in between, Expedia can help you find the right place in a few simple clicks.
Why book your villa in Castiglione del Bosco with Expedia?
Reserving a villa in Castiglione del Bosco is as easy as entering your travel dates and picking the option that has what you need. Searching for something luxurious or low cost, or a stay that also includes free WiFi? Use Expedia's search filters to narrow your results and find the perfect pad.