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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Castiglione del Bosco vacation rentals

Premium bedding, down comforters, pillowtop beds, individually furnished

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 P4,612
P5,987 total
includes taxes & fees
Jul 19 - Jul 20
Tuscasì Aparthotel
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 P6,609
P7,481 total
includes taxes & fees
Jul 15 - Jul 16
Abbadia Sicille Relais
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 P5,431
P6,325 total
includes taxes & fees
Jul 22 - Jul 23
RESIDENCE LECCIO
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is P4,596
P5,337 total
includes taxes & fees
Jul 15 - Jul 16
Residenza Fabroni
Breakfast, lunch and dinner served

Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (1 review)
"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 P18,479
P20,889 total
includes taxes & fees
Jul 19 - Jul 20
Palazzo Saloni
Seasonal outdoor pool, sun loungers

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (4 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 P9,342
P10,487 total
includes taxes & fees
Jul 13 - Jul 14
Residence Arianna
Exterior

Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (7 reviews)
"Loved everything about my stay"
United States
Svetlana
The price is P11,831
P13,716 total
includes taxes & fees
Jul 26 - Jul 27
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 traveler
The price is P11,034
P12,418 total
includes taxes & fees
Jul 16 - Jul 17
Casanova - Panoramic Rooms and Suites
Laptop workspace, iron/ironing board, free WiFi

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is P6,465
P7,393 total
includes taxes & fees
Jul 14 - Jul 15
TuscanyLettings Studio&Room
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is P7,372
P8,390 total
includes taxes & fees
Jul 26 - Jul 27
Il Pozzo di Sant'Andrea
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, (98 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is P9,068
P10,256 total
includes taxes & fees
Jul 19 - Jul 20
B&B Le Scalette di Piazza
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is P4,828
P5,591 total
includes taxes & fees
Jul 13 - Jul 14
Villa Fontis Rapolano
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is P8,535
P9,599 total
includes taxes & fees
Aug 6 - Aug 7
Casa di Campagna in Toscana
Courtyard view

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 P28,097
P31,188 total
includes taxes & fees
Jul 27 - Jul 28
L'Olmo
Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is P5,000
P5,500 total
includes taxes & fees
Jul 14 - Jul 15
La Dimora di Dida
Exterior

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is P5,109
P5,900 total
includes taxes & fees
Aug 1 - Aug 2
Villa le Camelie Siena
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (145 reviews)
"Great location."
United States
James
The price is P10,281
P11,590 total
includes taxes & fees
Aug 6 - Aug 7
La Locanda di San Francesco
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (173 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 P8,563
P9,982 total
includes taxes & fees
Jul 14 - Jul 15
Bosco della Spina
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (215 reviews)
"Friendly staff and good location."
Canada
Yongseok
The price is P8,966
P10,143 total
includes taxes & fees
Jul 30 - Jul 31
Il Battistero Siena - Residenza d'Epoca
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

Palazzo Ravizza

Palazzo Ravizza

8/10 Good
"Wonderful hotel and staff. Beautiful and well maintained property with a delicious breakfast included. Wifi isn’t strong but honestly I would stay here again i a heartbeat"
Amy 1-night trip
Posted 1 day ago
Palazzo Ravizza

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 I Canaloni del Torrente Farma. 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.