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Compare 522 Villas in Castiglione del Bosco with updated reviews, rates, and availability.

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

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

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 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!!!

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!

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (1)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

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."
The price is AED 1,722
AED 2,047 total
includes taxes & fees
3 Dec - 4 Dec
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!

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

Independent holiday house surrounded by a wide fenced garden with pool , located in the Tuscan coun

8.0 out of 10, Very Good, (2)
"Man muss ich bewusst sein, dass man immer ca. 30 Minuten durch die Berge fahren muss, um in größere Dörfer / Städtchen zu kommen."
Independent holiday house surrounded by a wide fenced garden with pool , located in the Tuscan coun

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 Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm

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....
panoramica casa con piscina privata

Villa Scopetello with Pool and Tennis court near Montepulciano and Siena

10.0 out of 10, Exceptional, (100)
"A wonderful setting, terrific location and ideal large house for our 3 generation group of extended family members. The 8 children under 11ys had a fantastic time playing with their cousins enjoying the grounds, pool area, tennis court and football goalposts. Sonja was a great host - relaxed but responsive and a thoughtful cook for the two prepared meals she made for us"
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena

A private luxury retreat in Montalcino

9.4 out of 10, Exceptional, (55)
"Lovely villa, great host. We really enjoyed our stay. "
A private luxury retreat in Montalcino

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

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

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

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 AED 562
AED 651 total
includes taxes & fees
2 Dec - 3 Dec
Il Poggio dell'Eremita

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

Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma

9.8 out of 10, Exceptional, (18)
"It was a perfect stay! Very helpful hosts with great local suggestions."
Villa "Il Diaccio" with a panoramic view of the Tuscan Maremma
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

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (142)
"The service at this hotel was impeccable. We were running late for our wine tasting but they were still SO accommodating! The rooms were beautiful and the view from the hotel are amazing. It was super accessible to everything. Also, the parking options were great - highly recommend. They're so responsive through texting and it was great to have this level of service. Highly rec! "
The price is AED 418
AED 469 total
includes taxes & fees
9 Dec - 10 Dec
Il Battistero Siena - Residenza d'Epoca

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (104)
"Very nice staff, great service, super clean. Will stay again."
Hotel San Gregorio

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (152)
"Beyond the peace and tranquility offered by the setting, it truly felt like the guests’ wellbeing was prioritized- the spaces (I viewed three before making a decision) were clean and orderly, the staff was incredibly attentive, the restaurant was enjoyable, and the overall experience was a very positive one."
The price is AED 193
AED 223 total
includes taxes & fees
2 Dec - 3 Dec
Abbadia Sicille Relais
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 AED 562 and AED 1,722 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 522 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.