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

Our top choices for Castiglione del Bosco holiday rentals

Desk, soundproofing, free WiFi, bed sheets

1. 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 S$197
includes taxes & fees
4 Aug - 5 Aug
B&B Le Scalette di Piazza
Breakfast, lunch and dinner served

2. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (4 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 S$373
includes taxes & fees
1 Aug - 2 Aug
Palazzo Saloni
Exterior

3. 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 S$162
includes taxes & fees
18 Aug - 19 Aug
Idolina Guest House
Exterior

4. 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 S$247
includes taxes & fees
30 Aug - 31 Aug
Corte Francigena - Apartments
Aerial view

5. 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 S$238
includes taxes & fees
31 Aug - 1 Sept
Bosco della Spina
1 treatment room, massages

6. 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)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is S$248
includes taxes & fees
31 Aug - 1 Sept
Casanova - Panoramic Rooms and Suites
Front of property

7. 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 S$133
includes taxes & fees
7 Aug - 8 Aug
RESIDENCE LECCIO
Couples treatment room(s), sauna, hot tub, steam room, body treatments

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, (49 reviews)
"Our stay was great. "
United States
Elena
The price is S$147
includes taxes & fees
2 Aug - 3 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Premium bedding, down duvets, pillow-top beds, desk

9. 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 S$132
includes taxes & fees
5 Aug - 6 Aug
Tuscasì Aparthotel
Seasonal outdoor pool

10. 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 S$410
includes taxes & fees
26 Aug - 27 Aug
Albergo Diffuso Borgo Santo
Food and drink

11. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is S$334
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Terrace/patio

12. 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 S$280
includes taxes & fees
31 Aug - 1 Sept
Abbadia Sicille Relais
Courtyard view

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 S$656
includes taxes & fees
3 Aug - 4 Aug
L'Olmo
Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

14. Podere Vesta

Podere Vesta
3.0 star property
Asciano
9.2 out of 10, Wonderful, (20 reviews)
"This was the best stay and experience during our 20 days trip to italy. Beautiful property 20min from Siena. It had everything we needed. The apartment is stocked with everything you could need for a long stay. My son had so much fun, and the free bikes were a plus. Make sure to pass by a grocery store before arriving, you won’t want to leave the property"
United States
Katerine
The price is S$269
includes taxes & fees
30 Aug - 31 Aug
Podere Vesta
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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"Loved our stay at the property. Extremely friendly and attentive staff, beautifully clean rooms, delicious breakfast and a great pool area."
Frederick 4-night trip
Posted 1 day ago
Villa Scacciapensieri Boutique Hotel

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.