A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.

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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Castiglione del Bosco holiday rentals

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

1. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (101 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is 3.493.082 ₫
3.962.714 ₫ total
includes taxes & fees
20 Sept - 21 Sept
B&B Le Scalette di Piazza
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

2. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is 3.686.907 ₫
4.296.126 ₫ total
includes taxes & fees
10 Oct - 11 Oct
Idolina Guest House
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

3. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (6 reviews)
"Excellent boutique hotel with a very welcoming staff. Rooms were wonderful. Location was terrific - very easy short walk to restaurants in town. Would highly recommend"
United States
BRIAN
The price is 9.236.011 ₫
10.460.303 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Palazzo Saloni
A poolside area with two glasses of water, candles, and a stone pathway.

4. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (95 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is 4.810.579 ₫
5.411.901 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Casanova - Panoramic Rooms and Suites
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

5. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (178 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is 2.904.688 ₫
3.435.685 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Bosco della Spina
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

6. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (13 reviews)
"The apartments and pool are fantastic. The location and breakfast boxes are perfect. The only real complaint was the parking lot was difficult to manage even in a smaller SUV. Staff were extremely communicative and made everything very easy for us."
United States
Ryan
The price is 4.356.581 ₫
5.092.900 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Corte Francigena - Apartments
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

7. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (49 reviews)
"Our stay was great. "
United States
Elena
The price is 6.247.279 ₫
6.992.271 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

8. Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (13 reviews)
"Beautiful stay "
United States
Marc
The price is 9.429.828 ₫
10.673.472 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Borgo Lucignanello Bandini
A person in a swimming pool with a view of trees and distant hills.

9. Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
10.0 out of 10, Exceptional, (2 reviews)
"Location was perfect, restaurants were excellent, views spectacular. Will highly recommend!"
United States
David
The price is 5.953.091 ₫
6.698.731 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Albergo Diffuso Borgo Santo
A patio area with outdoor seating, potted plants, and a view of the landscape.

10. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (65 reviews)
"I had a fantastic experience with this place. Great people!!!"
South Korea
Young Rok
The price is 2.915.047 ₫
3.955.198 ₫ total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
A historic building with a tower, a courtyard, and a well-lit entrance.

11. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 3.608.411 ₫
4.059.450 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Abbadia Sicille Relais
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

12. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (155 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.269.224 ₫
5.976.543 ₫ total
includes taxes & fees
10 Oct - 11 Oct
Hotel San Gregorio
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

13. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is 18.941.654 ₫
20.956.083 ₫ total
includes taxes & fees
14 Sept - 15 Sept
L'Olmo
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

14. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.155.741 ₫
2.461.513 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Tuscasì Aparthotel

15. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (7 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is 3.566.935 ₫
4.013.826 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Residence Arianna
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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Top Castiglione del Bosco Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Excellent location. Easy parking and helpful staff."
Tracy 1-night trip
Posted 4 hours ago
Hotel Chiusarelli

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’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 Val di Merse. 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.