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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 485 Villas in Castiglione del Bosco with updated reviews, rates, and availability.

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
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
Il Boschetto an oasis of peace and nature in Siena
Exterior

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
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (48)
"We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful."
The price is SAR 577
SAR 659 total
includes taxes & fees
24 Feb - 25 Feb
Il Poggio dell'Eremita
Villa with private pool and panoramic view in beautiful Val d'Orcia
Pool

Villa with private pool and panoramic view in beautiful Val d'Orcia

10.0 out of 10, Exceptional, (5)
"We had stayed at this property for years before Jennifer purchased it. And do hope to continue. We appreciate the effort and care to details she put into updating it and providing an excellent experience. This property is well located to see numerous villages in the area."
Villa with private pool and panoramic view in beautiful Val d'Orcia
Stunning private villa for 4 guests with WIFI, pool, A/C, TV, terrace and parking
Water, Plant, Sky, Building, Swimming Pool, Azure, Tree, Shade, Outdoor Furniture, Grass

Stunning private villa for 4 guests with WIFI, pool, 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...
Stunning private villa for 4 guests with WIFI, pool, A/C, TV, terrace and parking
Villa in Montalcino, exclusive for you, stunning view!!!
Exterior

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!!!
Villa Larniano, With Private Pool And View On Vineyard
Pool

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
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Pool

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Our Anglican Church friends (three couples) from Texas began our Italy tour in Rome and then continued to Florence for a few days. We spent our final four days at the beautiful Villa Santa Chiara, a short walk from the gates of downtown Siena, Italy. This wonderful villa could accommodate more people than our group of six, but it was an excellent choice for our three couples. Each couple had their own private apartment with a bathroom, kitchen, and spacious living area. The villa was...
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Private Villa with WIFI, private pool, A/C, TV, patio, panoramic view, parking, close to Montalcino
Outdoor

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

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

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...
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Villa luna with pool and garden near the center of Siena
Outdoor dining

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
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 con vista panoramica
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 353
SAR 628 total
includes taxes & fees
4 Mar - 5 Mar
panoramica casa con piscina privata
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, (94)
"We had the most amazing stay at this beautiful villa. Everything about it was picturesque and relaxing. This villa has all of the modern amenities but still exudes Tuscan charm. Pre- visit communication was smooth and very prompt. The highlight of the stay was the dinner cooked for us the first night by Chef Vanna and Francesca. I am not exaggerating when I say it was by far the best meal we had during our trip to Tuscany and we ate at many very nice restaurants. If you are booking a stay I...
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
The veranda at sunset

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
Historic Holding with wonderful swimming pool near Siena, Tuscany, Italy
La Palazzina main villa

Historic Holding with wonderful swimming pool near Siena, Tuscany, Italy

10.0 out of 10, Exceptional, (8)
"Tutto come ce lo aspettavamo, il chè non sempre avviene ma in questo caso SI."
Historic Holding with wonderful swimming pool near Siena, Tuscany, Italy
Tuscan stone villa with private pool surrounded by greenery
Pool

Tuscan stone villa with private pool surrounded by greenery

10.0 out of 10, Exceptional, (89)
"My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa...
Tuscan stone villa with private pool surrounded by greenery
Beautifully restored Tuscan villa, with private pool and breathtaking views
Pool

Beautifully restored Tuscan villa, with private pool and breathtaking views

10.0 out of 10, Exceptional, (16)
"We were a group of 10 using this house as a home base for our daily travels throughout Tuscany. Cally and Alex were fabulous. They were always quick to answer any questions we had. The house was so special…simply fabulous. Every inch of the house was just perfect. I was sad we didn’t get to spend more time enjoying the house and the amazing property. We had one night with Chef Ricardo who was incredible. He had such energy and passion, and his food was delicious! I can’t say enough wonderful...
Beautifully restored Tuscan villa, with private pool and breathtaking views
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Living area

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

9.6 out of 10, Exceptional, (37)
"Our family had a fantastic time in this rural villa. The space was very clean and well-kept as were the grounds (almost too much as they were there mowing grass several times during our stay and for most of the day). The surroundings were very peaceful and quiet and the countryside views were breathtaking with many outdoor areas on the property to enjoy - perfect for meals al fresco! Property is wonderfully located and ideal for day trips in Tuscany/Umbria from this home base but made sure we...
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
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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Other property types in Castiglione del Bosco

Hotel San Gregorio
Outdoor pool

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (110)
"Very nice staff, great service, super clean. Will stay again."
The price is SAR 465
SAR 535 total
includes taxes & fees
6 Mar - 7 Mar
Hotel San Gregorio
Il Battistero Siena - Residenza d'Epoca
Room

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (151)
"Wonderful location!!! Everything within walking distance. Friendly staff, clean modern room. Shower needs repairing. Will definitely return to stay here. If you are driving to the hotel, It’s a ZTL zone so contact the hotel to make arrangements for your car to be garaged. Don’t need a car here. It is in the best location!!!"
The price is SAR 536
SAR 605 total
includes taxes & fees
24 Feb - 25 Feb
Il Battistero Siena - Residenza d'Epoca
Casanova - Panoramic Rooms and Suites
Aerial view

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (42)
"It was a nice property- unfortunate what they charge to just swim"
The price is SAR 649
SAR 734 total
includes taxes & fees
14 Mar - 15 Mar
Casanova - Panoramic Rooms and Suites
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?
Prices for villas in Castiglione del Bosco range between SAR 353 and SAR 577 per night. No matter your budget, you’re sure to find someplace that matches your needs with 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?
Make use of your vacation days and pick from 485 villas in Castiglione del Bosco. For a vacation with the family, a getaway with friends or anything in between, Expedia will help you find an ideal stay in a few easy clicks.
Why book your villa in Castiglione del Bosco with Expedia?
With Expedia, it’s a cinch to find your ideal villa in Castiglione del Bosco. Vacationing with the kids? Make the most of our helpful filters to look for stays with amenities like a pool. If you’re on a budget, select how much you’d like to spend and your preferred star rating. We’ll help you find the perfect fit that gels with your style and taste.
How can I find cheap villas in Castiglione del Bosco?
With Expedia’s handy filter tool, locating cheap villas in Castiglione del Bosco couldn’t be easier. To find stays that are easy on your bank balance, tailor your search results by budget, amenities and star rating.