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

Castiglione del Bosco Holiday Rentals

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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 wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

1. 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 S$133
includes taxes & fees
25 Nov - 26 Nov
Idolina Guest House
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

2. 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 S$137
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

3. 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 S$173
includes taxes & fees
2 Nov - 3 Nov
B&B Le Scalette di Piazza
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

4. 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 S$370
includes taxes & fees
29 Nov - 30 Nov
Palazzo Saloni
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 S$173
includes taxes & fees
3 Nov - 4 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, (104 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 S$245
includes taxes & fees
24 Nov - 25 Nov
Casanova - Panoramic Rooms and Suites
A stone building with a courtyard, outdoor seating, and a warm light setting.

7. 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 S$168
includes taxes & fees
11 Nov - 12 Nov
Sarna Residence
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

8. 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 S$201
includes taxes & fees
5 Nov - 6 Nov
Hotel San Gregorio
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

9. 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 S$150
includes taxes & fees
3 Nov - 4 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A villa with a swimming pool, outdoor seating, and a tennis court.

10. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (83 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is S$190
includes taxes & fees
31 Oct - 1 Nov
Villa Curina Resort
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.

11. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$106
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

12. 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 S$96
includes taxes & fees
26 Nov - 27 Nov
Abbadia Sicille Relais
A patio area with outdoor seating, potted plants, and a view of the landscape.

13. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is S$176
includes taxes & fees
3 Nov - 4 Nov
Affitacamere Maria Gabriella
An arched stone gateway leading to a pathway lined with potted plants and lights.

14. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is S$259
includes taxes & fees
31 Oct - 1 Nov
Castello di Modanella
A person in a swimming pool with a view of trees and distant hills.

15. 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 S$287
includes taxes & fees
23 Nov - 24 Nov
Albergo Diffuso Borgo Santo
A stone courtyard with a bench, potted plants, and a building in the background.

16. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is S$121
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
A stone-paved courtyard with a wrought iron gate, a brick building, and a tree.

17. B&B Le Logge Di Sopra

B&B Le Logge Di Sopra
Asciano
The price is S$151
includes taxes & fees
24 Nov - 25 Nov
B&B Le Logge Di Sopra
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

18. 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 S$101
includes taxes & fees
12 Nov - 13 Nov
RESIDENCE LECCIO
A crowded restaurant with brick walls and multiple tables and chairs.

19. 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 S$213
includes taxes & fees
26 Nov - 27 Nov
La Locanda di San Francesco
Exterior

20. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is S$167
includes taxes & fees
31 Oct - 1 Nov
montorio
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 Athena

Hotel Athena

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 9 hours ago
Hotel Athena

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.