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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Castiglione del Bosco vacation rentals

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

1. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is P7,335
P8,350 total
includes taxes & fees
Oct 14 - Oct 15
B&B Le Scalette di Piazza
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, (183 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 P5,565
P6,685 total
includes taxes & fees
Nov 1 - Nov 2
Bosco della Spina
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)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is P5,348
P6,447 total
includes taxes & fees
Oct 27 - Oct 28
Idolina Guest House
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, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is P16,191
P18,514 total
includes taxes & fees
Nov 9 - Nov 10
Palazzo Saloni
A poolside area with two glasses of water, candles, and a stone pathway.

5. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is P10,695
P12,046 total
includes taxes & fees
Oct 12 - Oct 13
Casanova - Panoramic Rooms and Suites
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

6. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is P7,680
P9,010 total
includes taxes & fees
Nov 8 - Nov 9
Corte Francigena - Apartments
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, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P3,904
P5,209 total
includes taxes & fees
Nov 2 - Nov 3
Tuscasì Aparthotel
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, (161 reviews)
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
United States
Julia
The price is P8,124
P9,359 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
A villa with a swimming pool, outdoor seating, and a tennis court.

9. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is P7,614
P8,657 total
includes taxes & fees
Oct 18 - Oct 19
Villa Curina Resort
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

10. 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 P6,560
P7,497 total
includes taxes & fees
Nov 2 - Nov 3
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A stone building with a courtyard, outdoor seating, and a warm light setting.

11. 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 P6,972
P8,514 total
includes taxes & fees
Nov 3 - Nov 4
Sarna Residence
A patio area with outdoor seating, potted plants, and a view of the landscape.

12. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is P6,822
P9,256 total
includes taxes & fees
Oct 12 - Oct 13
Affitacamere Maria Gabriella
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

13. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is P28,146
P31,242 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

14. Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful stay "
United States
Marc
The price is P21,695
P24,568 total
includes taxes & fees
Oct 15 - Oct 16
Borgo Lucignanello Bandini
A historic building with a tower, a courtyard, and a well-lit entrance.

15. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is P5,469
P6,227 total
includes taxes & fees
Nov 10 - Nov 11
Abbadia Sicille Relais
Outdoor pool

16. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is P8,348
P9,394 total
includes taxes & fees
Nov 9 - Nov 10
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

Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed here for three nights and absolutely loved it. The hotel is charming, convenient and comfortable. Breakfast was very good, with a nice choice of foods, and the lounge/bar is a great place to relax. The staff were very helpful with directions and bookings. We would gladly stay here again."
Ralph 2-night trip
Posted 8 hours ago
Hotel Italia

Find out more about Castiglione del Bosco

Search for holiday rentals in Castiglione del Bosco on Expedia! You can easily find your home rentals, villas, holiday apartments in Castiglione del Bosco using one of the methods below:

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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 Horti Leonini. 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.