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
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Castiglione del Bosco holiday rentals

Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (99 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is 3.622.677 ₫
4.104.613 ₫ total
includes taxes & fees
4 Aug - 5 Aug
B&B Le Scalette di Piazza
Breakfast, lunch and dinner served

Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay! The staff are exceptional- so helpful and kind with every aspect of the stay. The rooms are beautiful and lovely amenities upon arrival. Would definitely go back again!"
United States
Victoria
The price is 6.646.662 ₫
7.550.754 ₫ total
includes taxes & fees
1 Aug - 2 Aug
Palazzo Saloni
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (175 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 4.626.257 ₫
5.328.219 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Bosco della Spina
Exterior

Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"This is a wonderful B&B that is part of the historic district. Sloping uneven floors, which is the charm of having the chance to stay in a piece of history. A very comfortable room, with breakfast at a cafe nearby. Parking option is nearby, just talk with your host who is so helpful. Wonderful location to walk and enjoy all the town has to offer."
United States
Sophie
The price is 2.482.381 ₫
2.969.955 ₫ total
includes taxes & fees
7 Aug - 8 Aug
Idolina Guest House
Exterior

Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"was such a beautiful location I dont have anything bad to say about it...would definitely go again for a relaxing and tranquil stay - you definitely need a car to get there though and to go around.."
United States
Hanna
The price is 4.562.246 ₫
5.317.776 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Corte Francigena - Apartments
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (92 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, and breakfast was excellent. Every part of our stay exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area."
United States
Anonymous traveller
The price is 5.956.177 ₫
6.671.493 ₫ total
includes taxes & fees
6 Aug - 7 Aug
Casanova - Panoramic Rooms and Suites
Premium bedding, down duvets, pillow-top beds, desk

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.033.314 ₫
2.625.567 ₫ total
includes taxes & fees
25 Aug - 26 Aug
Tuscasì Aparthotel
Couples treatment room(s), sauna, hot tub, steam room, body treatments

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, (48 reviews)
"Our stay was great. "
United States
Elena
The price is 2.589.966 ₫
2.968.630 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Seasonal outdoor pool

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 7.404.459 ₫
8.294.490 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Albergo Diffuso Borgo Santo
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 2.314.183 ₫
2.695.255 ₫ total
includes taxes & fees
31 Jul - 1 Aug
RESIDENCE LECCIO
Terrace/patio

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 4.797.600 ₫
5.367.111 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Abbadia Sicille Relais
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (151 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.999.887 ₫
6.779.459 ₫ total
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Front of property – evening/night

Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (98 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is 3.634.916 ₫
4.147.992 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Residence Borgo San Lorenzo a Linari
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Amazing hotel for 1 night to see Siena quickly! Easy parking and very helpful and lovely staff. Great location."
Ashley 1-night trip
Posted 4 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

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.