Photo by Mario Mürner

Search Villas in Castiglione del Bosco

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

Compare 589 Villas in Castiglione del Bosco with updated reviews, rates, and availability.

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)
"What an incredible place! Patrick and his team made our stay a luxurious and memorable experience! The estate, especially the infinity-edge swimming pool are surrounded by stunning views of quintessential Tuscan courtyside, which made for some pretty epic sunsets! We also loved the lake and th golf buggies! The rooms all have private access so you have the privacy of a hotel, but with the common areas and kitchen, which were very well equipped. The daily housekeeping and cleaning of the common...
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Outdoor pool

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

10.0 out of 10, Exceptional, (7)
"We stayed together with children and grandchildren and had a great stay. The house and grounds were beautiful and well kept and we had everything needed."
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Winery Villa in the heart of Nobile Vineyards.
Interior

Winery Villa in the heart of Nobile Vineyards.

9.8 out of 10, Exceptional, (10)
"We love our stay. House and property are beautiful."
Winery Villa in the heart of Nobile Vineyards.
Beautiful private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking
Pool

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

9.8 out of 10, Exceptional, (28)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Beautiful private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking
Il Poggio dell'Eremita
Interior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (49)
"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 537
SAR 623 total
includes taxes & fees
13 Apr - 14 Apr
Il Poggio dell'Eremita
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

10.0 out of 10, Exceptional, (78)
"We absolutely loved our stay at this villa! It was just wonderful, and Luigi was a fantastic host! The views from every part of the villa are amazing! It was so fun to see all of the sheep each morning and watch the sunset in the evenings. We were fortunate enough to be in town for the olive festival in Montisi, the quaint little village just a few miles away. We had a blast! The recommended chef who cooked for us at the villa, Giancarlo from the Tuscan Chef, was incredible! What a fantastic...
Villa in Montalcino, exclusive for you, stunning view!!!
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, (95)
"Beautiful home, beautiful views. "
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Storico Villa Ferrano con comfort moderni e piscina, ideale per i grandi eventi
Exterior

Storico Villa Ferrano con comfort moderni e piscina, ideale per i grandi eventi

Storico Villa Ferrano con comfort moderni e piscina, ideale per i grandi eventi
Exclusive villa with park and private swimming pool in Siena
A heated pool

Exclusive villa with park and private swimming pool in Siena

10.0 out of 10, Exceptional, (1)
"Ottima esperienza accompagnata dalla cordialità dei proprietari. La villa è una comoda base per visitare Siena e i dintorni. Al rientro si può godere della piscina e del panorama delle colline tra gli ulivi. La proprietaria è un'ottima cuoca se si desidera una vera cena toscana"
Exclusive villa with park and private swimming pool in Siena
Villa in Siena with 4 bedrooms sleeps 8
TV

Villa in Siena with 4 bedrooms sleeps 8

10.0 out of 10, Exceptional, (42)
"We spent an unforgettable week. Beautiful nature, wonderful Siena, Florence, San Gimignano, villa Capannna di Elfo. Exceptional hosts Angelica and Claudio!"
Villa in Siena with 4 bedrooms sleeps 8
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, (64)
"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
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)
"The home had everything we needed. The view from the villa was truly picturesque. A+++++!"
Villa luna with pool and garden near the center of Siena
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)
"This house is very nice. It is centrally located outside Siena and good location to explore all over Tuscany. It is off the beaten path so you’ll definitely need a rental car. Even just to get there. It is remote. Which is a plus but also has some drawbacks. We went in March so pool was closed. Too cold to swim. House is several levels. Kitchen and dining room are downstairs. We cooked several simple meals after going into town to grab groceries. Nearby town is nice. Not a lot of restaurant...
The price is SAR 3,053
SAR 4,073 total
includes taxes & fees
25 Apr - 26 Apr
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino
Pool

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 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 SAR 369
SAR 652 total
includes taxes & fees
18 Apr - 19 Apr
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, (45)
"Luigi went above and beyond in providing suggestions of restaurants and things to do in the area. He was also helpful when we were have trouble calling our car rental….always willing to help out and answer questions. The home is very clean and has the old Italian rustic charm. The beds were comfortable. There is no AC but fans are provided for every room. There were beautiful sunsets every night by the pool. The views of the rolling Tuscan hills were spectacular. The color and intensity of the...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Pool

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (55)
"Lovely villa, great host. We really enjoyed our stay. "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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, (31)
"The location was excellent, 30 minute walk (2.1 km) to the main gate of Siena or 15 minute bus ride (bus stop 25 meters from the house). The home is beautiful, lots of amenities, it was very rustic. The pool area could use a good trimming, the online photos showed the property better than it actually was but not too far off."
Il Boschetto an oasis of peace and nature in 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.
Don't see what you're looking for?
See all available properties in Castiglione del Bosco
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Castiglione del Bosco

Casanova - Panoramic Rooms and Suites
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Casanova - Panoramic Rooms and Suites

3.0 star property
9.2 out of 10, Wonderful, (44)
"We love it ! It is a wonderful place, it is perfectly for have a quit time and get relax. "
The price is SAR 667
SAR 750 total
includes taxes & fees
10 Apr - 11 Apr
Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Seasonal outdoor pool, sun loungers

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (111)
"Very nice staff, great service, super clean. Will stay again."
The price is SAR 571
SAR 653 total
includes taxes & fees
15 Apr - 16 Apr
Hotel San Gregorio
Il Battistero Siena - Residenza d'Epoca
Bar (on property)

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (154)
"Fabulous property and staff. Rita was so helpful when our car had to be towed, we wouldn't have been able to continue our trip with out her and the other team members help. The people here are amazing."
The price is SAR 563
SAR 635 total
includes taxes & fees
10 Apr - 11 Apr
Il Battistero Siena - Residenza d'Epoca
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.

Frequently asked questions

How much do villas in Castiglione del Bosco cost?
Rates for villas in Castiglione del Bosco range between SAR 369 and SAR 3,053 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 589 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.
How can I find cheap villas in Castiglione del Bosco?
With Expedia’s user-friendly filter tool, locating cheap villas in Castiglione del Bosco is a cinch. To discover properties that’ll make your wallet smile, refine your search results by budget, amenities and star rating.