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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 590 Villas in Castiglione del Bosco with updated reviews, rates, and availability.

Il Poggio dell'Eremita
Terrace/patio

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (51)
"Our family of 4 had such a beautiful time at this gorgeous villa. We only stayed for 2 nights, wish we stayed longer. Highly recommend!"
The price is AED 517
AED 601 total
includes taxes & fees
10 Jun - 11 Jun
Il Poggio dell'Eremita
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, (84)
"We had a wonderful stay, the location was perfect for a short 15 minute walk into Montisi. The countryside setting was lovely and peaceful. We enjoyed being surrounded by beautiful nature, watching the deer every evening was delightful. We hope to return in the future. "
Hilltop house in the heart of Tuscany with private pool
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Outdoor pool, a heated pool

Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake

10.0 out of 10, Exceptional, (45)
"AGRICOLA NECI is a luxury experience all the way. From the owner Patrick to the staff (Eva, Santiago and Gregorio) everyone was there to make sure our experience was memorable. The views of the surrounding valleys are incredible. The house itself is out of a movie. I highly recommend an extended vacation here."
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Beautiful private villa for 4 guests with WIFI, A/C, pool, TV, terrace and parking
Pool

Beautiful private villa for 4 guests with WIFI, A/C, pool, TV, terrace and parking

9.8 out of 10, Exceptional, (28)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Beautiful private villa for 4 guests with WIFI, A/C, pool, TV, terrace and parking
Il Boschetto an oasis of peace and nature in Siena
Outdoor pool

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (33)
"The rooms are spacious and well equipped and the house can easily accommodate 10 people. The property is located in a wealthy enclave of Siena minutes from town yet it is completely private. The views are breathtaking and the property is gorgeous."
Il Boschetto an oasis of peace and nature in Siena
Villa with unique view of Siena with private pool
Outdoor pool

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
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)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
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 A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Pool

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

Private Villa with A/C, private pool, WIFI, 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

8.8 out of 10, Excellent, (3)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
The price is AED 10,767
AED 11,809 total
includes taxes & fees
28 Jun - 29 Jun
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Exterior

Magnifica villa in toscana, 7 posti letto, con vista incredibile!!

10.0 out of 10, Exceptional, (2)
"Such a quaint home, clean, quiet and beautiful. Close to the center of the very small town of Montepulciano. The host is very sweet and even cooked a cake to welcome us to their home. The view of the valley from the home is simply breathtaking."
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Villa luna with pool and garden near the center of Siena
Fridge, microwave, oven, dishwasher

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
villa con vista panoramica
Outdoor pool

villa con vista panoramica

9.0 out of 10, Wonderful, (2)
"Die Wohnung liegt ruhig im schönen Dorf Chiusdino, das Meer ist ca. 1 Stunde entfernt, aber der Pool eignet sich gut zum Baden. Es ist genug Platz für 4 Personen. Der Vermiter Paolo ist sehr freundlich und hilfsbereit, die Kommunikation war super. Uns hat es sehr gut gefallen und wir kommen gerne wieder!"
villa con vista panoramica
panoramica casa con piscina privata
Pool

panoramica casa con piscina privata

7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
The price is AED 462
AED 769 total
includes taxes & fees
10 Jun - 11 Jun
panoramica casa con piscina privata
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Outdoor pool

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi

10.0 out of 10, Exceptional, (48)
"Exvellent Location close to all towns in Tuscany Good communication w Manager"
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Terrace/patio

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

10.0 out of 10, Exceptional, (98)
"Clean, very convenient, friendly.... Everything was super!"
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

10.0 out of 10, Exceptional, (80)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Exterior

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

9.6 out of 10, Exceptional, (37)
"The stay was very nice. It's a beautiful property and very photogenic! We all loved it, wish we had more time to spend and enjoy the house."
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Villa Dipendenza, Historic Holding with wonderful swimming pool
Outdoor pool

Villa Dipendenza, Historic Holding with wonderful swimming pool

10.0 out of 10, Exceptional, (36)
"We spent a week at this charming property and had an absolutely magical time with friends. The house was cozy and comfortable, with a beautiful balcony perfect for enjoying evening meals. The shared pool offered breathtaking views, and the other guests were incredibly friendly, adding to the warm atmosphere. Our host, Eloise, was exceptional—her hospitality and attention to detail made our stay even more special. She provided wonderful restaurant recommendations that we thoroughly enjoyed. We...
Villa Dipendenza, Historic Holding with wonderful swimming pool
Casale del Conte - Three Bedroom Villa, Sleeps 6
Game room

Casale del Conte - Three Bedroom Villa, Sleeps 6

10.0 out of 10, Exceptional, (6)
"Excellent location for those seeking privacy, friendly and helpful owners and a very roomy villa. Car is highly recommended!"
Casale del Conte - Three Bedroom Villa, Sleeps 6
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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Frequently asked questions

How much do villas in Castiglione del Bosco cost?
Rates for villas in Castiglione del Bosco range between AED 462 and AED 10,767 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 590 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.