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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Castiglione del Bosco holiday rentals

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

1. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is 7.198.277 ₫
8.205.536 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Palazzo Saloni
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

2. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"We had a great stay in this conveniently located property. The breakfast was good with many options and staff to assist."
Canada
Morris
The price is 3.057.421 ₫
3.478.262 ₫ total
includes taxes & fees
8 Nov - 9 Nov
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.

3. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is 2.121.851 ₫
2.565.088 ₫ total
includes taxes & fees
27 Nov - 28 Nov
Idolina Guest House
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

4. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (188 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is 2.284.259 ₫
2.743.737 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

5. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is 3.110.444 ₫
3.651.457 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Corte Francigena - Apartments
A poolside area with two glasses of water, candles, and a stone pathway.

6. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (103 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is 4.599.355 ₫
5.174.274 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Casanova - Panoramic Rooms and Suites
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.

7. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 1.594.829 ₫
2.128.010 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

8. 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, (50 reviews)
"Our stay was great. "
United States
Elena
The price is 3.150.270 ₫
3.580.310 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

9. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (168 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is 3.704.205 ₫
4.247.217 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Hotel San Gregorio
A stone building with a courtyard, outdoor seating, and a warm light setting.

10. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is 2.848.438 ₫
3.478.263 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Sarna Residence
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

11. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (224 reviews)
"Very nice hotel with wonderful staff. Very accommodating. Would highly recommend."
United States
Anthony
The price is 2.882.213 ₫
3.285.960 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Il Battistero Siena - Residenza d'Epoca
A villa with a swimming pool, outdoor seating, and a tennis court.

12. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is 3.753.962 ₫
4.244.342 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Villa Curina Resort
A table set with breakfast items on a balcony overlooking a historic town.

13. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (135 reviews)
"We had a great stay!"
United States
Suelina
The price is 3.919.904 ₫
4.426.878 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Residenza d'Epoca Palazzo Borghesi
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

14. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is 1.669.879 ₫
1.923.105 ₫ total
includes taxes & fees
26 Nov - 27 Nov
Abbadia Sicille Relais
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

15. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 1.914.052 ₫
2.249.864 ₫ total
includes taxes & fees
12 Nov - 13 Nov
RESIDENCE LECCIO
A person in a swimming pool with a view of trees and distant hills.

16. Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
10.0 out of 10, Exceptional, (3 reviews)
"Location was perfect, restaurants were excellent, views spectacular. Will highly recommend!"
United States
David
The price is 5.691.702 ₫
6.404.603 ₫ total
includes taxes & fees
27 Nov - 28 Nov
Albergo Diffuso Borgo Santo
A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (101 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is 1.787.476 ₫
2.081.208 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
A crowded restaurant with brick walls and multiple tables and chairs.

18. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is 4.043.401 ₫
4.563.267 ₫ total
includes taxes & fees
25 Nov - 26 Nov
La Locanda di San Francesco
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 Minerva

Hotel Minerva

10/10 Excellent
"Clean, great breakfast, lovely view!"
Tracy 2-night trip
Posted 1 day ago
Hotel Minerva

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 Horti Leonini. 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.