Photo by Mario Mürner

Holiday Rentals in Castiglione del Bosco

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Holiday Rentals in Castiglione del Bosco

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (150)
"Wonderful place. Super helpful staff, perfect location, comfortable and safe."
The price is €154
includes taxes & fees
18 Feb - 19 Feb
Il Battistero Siena - Residenza d'Epoca

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 €146
includes taxes & fees
18 Feb - 19 Feb
Hotel San Gregorio

ApartHotel Anghel

8.2 out of 10, Very good, (311)
"Nice place, quiet and clean!"
The price is €85
includes taxes & fees
20 Feb - 21 Feb
ApartHotel Anghel

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

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (155)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is €82
includes taxes & fees
9 Mar - 10 Mar
Abbadia Sicille Relais

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 €189
includes taxes & fees
13 Mar - 14 Mar
Casanova - Panoramic Rooms and Suites

Il Tosco

10.0 out of 10, Exceptional, (103)
"Wonderful total experience! Kind and generous service, available but not intrusive, perfect morning breakfast, beautiful linens in rooms and breakfast area. One couldn’t ask for more from hostess and owners! "
The price is €298
includes taxes & fees
1 Mar - 2 Mar
Il Tosco

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

9.8 out of 10, Exceptional, (66)
"The views from this house are fantastic! And the location is perfect - steps from the old town of Montepulciano. Communication with Erika, the host was great. She prepared us with lots of details and recommendations for things to do nearby. We had some questions during our stay and Erika was very responsive. There is so much to do in the area - I almost wished we had more time to hang out on the beautiful terraces!"
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Bosco della Spina

9.4 out of 10, Exceptional, (142)
"We were met by the property owner who was pleasant and informative. The room was exactly as depicted in the photos and property was in excellent condition. We would recommend to anyone staying the area at any time of year/ "
Bosco della Spina

agriturismo la roggiola

9.6 out of 10, Exceptional, (97)
"Mieliśmy bardzo udany listopadowy pobyt w cichym, czystym i cieplym miejscu , pośród toskańskiej przyrody,, z dala od miejskiego hałasu który mamy na codzień mieszkając w dużym mieście. Jedyne czego się obawialiśmy tylko że będzie trudno znaleźć domek, jako że przejeżdżaliśmy późno wieczorem ale mapy prowadziły doskonale a sama posiadłość była oświetlona i nie było w związku z tym żadnych problemów z trafieniem tam"
agriturismo la roggiola

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (58)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.

Residenza Fabroni

8.8 out of 10, Excellent, (79)
"This is a very large apartment in a 500 year old well maintained building. It is in the beautiful historic area. Do be aware that this is a VERY hilly area and you will have to walk up and down steep streets everywhere you go. That includes from the parking area. Cars are restricted from the area around the apartment without a permit. "
The price is €101
includes taxes & fees
19 Feb - 20 Feb
Residenza Fabroni

La Terrazza Sul Campo Rooming House

9.6 out of 10, Exceptional, (221)
"Excellent location. Excellent service. Great view from the balcony. "
The price is €110
includes taxes & fees
18 Feb - 19 Feb
La Terrazza Sul Campo Rooming House

Regis Condo

9.2 out of 10, Wonderful, (55)
"This place is huge, two bathrooms, sitting area, kitchen. The staff gave good instructions and were very responsive. Very close to the main cathedral. "
The price is €94
includes taxes & fees
23 Feb - 24 Feb
Regis Condo

Osteria del Borgo

9.2 out of 10, Wonderful, (142)
"Communication with owner excellent. Was able to drop bags at unit and then park car in space provided by hotel about a 10 minute walk down or up depending on direction. Apartment large and comfortable. Breakfast nice continental assortment. Owner helped with bags up 2 flights of stairs checking in. Excellent location. Every thing nearby. We would book again"
Osteria del Borgo

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 €162
includes taxes & fees
25 Feb - 26 Feb
panoramica casa con piscina privata

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

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

Residenza d'Epoca Palazzo Borghesi

9.6 out of 10, Exceptional, (108)
"This property is gorgeous and the stay here was amazing! Our room had the private terrace and we had breakfast out there the next morning! I can’t tell you how picturesque, stunning and just plain peaceful our breakfast was out in the terrace! The morning fog covered the valley, all you could see were the church steeples peaking through, you heard the nice old ladies talking in the streets below while going out for morning bread, the birds were tweeting and cooing. I’m serious here, it was a...
The price is €148
includes taxes & fees
22 Feb - 23 Feb
Residenza d'Epoca Palazzo Borghesi

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 €172
includes taxes & fees
18 Feb - 19 Feb
Il Poggio dell'Eremita
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 types of properties in Castiglione del Bosco you may be interested in

Rosewood Castiglion del Bosco

5.0 star property
10.0 out of 10, Exceptional, (57)
"Rosewood Castiglion Del Bosco is an exceptional hotel offering a stunning view of Val d'Orcia, a beautiful valley in Tuscany. The picturesque surroundings provide a truly memorable experience for guests seeking a peaceful retreat. The hotel's ambiance and service are top-notch, creating a luxurious and comfortable stay. One minor drawback that I encountered during my visit in the winter was that the temperature of the indoor pool was not as warm as I would have preferred. While the pool area is...
Rosewood Castiglion del Bosco

Hotel Chiusarelli

3.0 star property
8.8 out of 10, Excellent, (1001)
"Well located and walking distance to many key spots. Lorenzo was very helpful and nice hotel."
The price is €78
includes taxes & fees
23 Feb - 24 Feb
Hotel Chiusarelli

Hotel Italia

3.0 star property
9.2 out of 10, Wonderful, (1000)
"Great location, very close to the train station and the old city. Super friendly staff, great facilities. I loved it :)"
The price is €81
includes taxes & fees
23 Feb - 24 Feb
Hotel Italia
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

Can I find holiday rentals in Castiglione del Bosco?

Yes, there are holiday rentals close to the most popular sights in Castiglione del Bosco, or you can select a more secluded option if you're looking for a relaxing stay. Castiglione del Bosco is known for its restaurants.

What are some of the best holiday rentals that Castiglione del Bosco has to offer?

Beautiful stone house with garden and private pool.: This holiday home rental outside of Castiglione del Bosco is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

What’s there to see and do in Castiglione del Bosco?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like I Canaloni del Torrente Farma. Castiglion del Bosco Winery and Fortress of Montalcino are a couple of places you'll find in the wider area.

What’s a holiday rental in Castiglione del Bosco like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castiglione del Bosco. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.