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

Castiglione del Bosco Vacation Rentals

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Check prices for these dates

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

Our top choices for Castiglione del Bosco vacation rentals

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

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 ₩181,725
₩206,158 total
includes taxes & fees
Sep 15 - Sep 16
B&B Le Scalette di Piazza
Front of property

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 ₩195,806
₩227,900 total
includes taxes & fees
Sep 23 - Sep 24
Idolina Guest House
Breakfast, lunch and dinner served

3. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (5 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 ₩502,308
₩565,047 total
includes taxes & fees
Sep 11 - Sep 12
Palazzo Saloni
1 treatment room, massages

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, (94 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is ₩237,754
₩267,786 total
includes taxes & fees
Sep 13 - Sep 14
Casanova - Panoramic Rooms and Suites
Aerial view

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 ₩151,114
₩178,738 total
includes taxes & fees
Oct 5 - Oct 6
Bosco della Spina
Exterior

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 ₩232,536
₩271,432 total
includes taxes & fees
Oct 5 - Oct 6
Corte Francigena - Apartments
Couples treatment rooms, sauna, hot tub, steam room, body treatments

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 ₩218,984
₩247,140 total
includes taxes & fees
Sep 9 - Sep 10
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Terrace/patio

8. Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (13 reviews)
"Beautiful stay "
United States
Marc
The price is ₩490,581
₩555,281 total
includes taxes & fees
Oct 1 - Oct 2
Borgo Lucignanello Bandini
Seasonal outdoor pool

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 ₩387,132
₩433,666 total
includes taxes & fees
Sep 28 - Sep 29
Albergo Diffuso Borgo Santo
Panoramic Cottage, 1 Bedroom | Exterior

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 ₩151,654
₩205,768 total
includes taxes & fees
Oct 4 - Oct 5
Affitacamere Maria Gabriella
Front of property - evening/night

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 ₩187,725
₩211,190 total
includes taxes & fees
Oct 6 - Oct 7
Abbadia Sicille Relais
Food and drink

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 ₩267,678
₩303,831 total
includes taxes & fees
Oct 6 - Oct 7
Hotel San Gregorio
Suite, 2 Bedrooms | 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 ₩985,428
₩1,090,228 total
includes taxes & fees
Sep 14 - Sep 15
L'Olmo
Premium bedding, down comforters, pillowtop beds, desk

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 ₩110,653
₩142,053 total
includes taxes & fees
Oct 4 - Oct 5
Tuscasì Aparthotel
Seasonal outdoor pool, sun loungers

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 ₩185,568
₩208,818 total
includes taxes & fees
Sep 16 - Sep 17
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"All the staff in the hotel were very helpful and we would like to stay there again."
Richard 2-night trip
Posted 5 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Castiglione del Bosco

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Frequently asked questions

Can I find vacation rentals in Castiglione del Bosco?

Yes, there are vacation rentals close to well known attractions in Castiglione del Bosco, or you can choose a more secluded option if you want a relaxing place to 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 larger area.

What’s a vacation rental in Castiglione del Bosco like?

A vacation rental is a private property where you can stay for short or long periods in Castiglione del Bosco. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip.