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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Villas in Castiglione del Bosco

Pool
panoramica casa con piscina privata

panoramica casa con piscina privata

siena
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
The price is SAR 354
SAR 655 total
includes taxes & fees
15 Dec - 16 Dec
panoramica casa con piscina privata
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is SAR 531
SAR 618 total
includes taxes & fees
8 Dec - 9 Dec
Il Poggio dell'Eremita
Terrace/patio
Antico Brunello

Antico Brunello

Montalcino
The price is SAR 28,841
SAR 31,768 total
includes taxes & fees
8 Dec - 9 Dec
Antico Brunello
Exterior
'...a delicious farmhouse in the countryside where only the wind blows...'

'...a delicious farmhouse in the countryside where only the wind blows...'

Campiglia d'Orcia
10.0 out of 10, Exceptional, (7)
"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...
United States
Li-Shen L.
The price is SAR 4,151
SAR 6,786 total
includes taxes & fees
10 Dec - 11 Dec
'...a delicious farmhouse in the countryside where only the wind blows...'
Exterior
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino
The price is SAR 26,000
SAR 28,185 total
includes taxes & fees
8 Dec - 9 Dec
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena
The price is SAR 26,146
SAR 26,146 total
includes taxes & fees
8 Dec - 9 Dec
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Exterior
Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.

Trequanda
The price is SAR 2,403
SAR 4,007 total
includes taxes & fees
9 Dec - 10 Dec
Red Heart - relax with those you love in Tuscany.
Outdoor dining
Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Rapolano Terme
9.0 out of 10, Wonderful, (4)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is SAR 2,132
SAR 3,215 total
includes taxes & fees
14 Dec - 15 Dec
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Exterior
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR
The price is SAR 4,999
SAR 5,283 total
includes taxes & fees
8 Dec - 9 Dec
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
A heated pool
POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10

POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10

Siena
8.0 out of 10, Very Good, (1)
"Villa magnifique dans un environnement superbe. Les chambres sont d'un grand confort. S'agissant d'une maison récemment rénovée, quelques réglages sont à réaliser pour atteindre la perfection : nombre de fauteuils bain de soleil insuffisant, améliorer la protection solaire sur la terrasse extérieure et le nombre de fauteuils ; petites difficultés liées à l'usage du lave linge mais très vite réglées. Globalement c'est un très agréable séjour dans une magnifique demeure, rénovée avec goût et...
France
Pierre V.
The price is SAR 7,800
SAR 9,111 total
includes taxes & fees
3 Jan - 4 January 2026
POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10
Outdoor dining
Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany

Vico dʼArbia
The price is SAR 5,537
SAR 5,970 total
includes taxes & fees
8 Dec - 9 Dec
Villa Capanna: A Window onto Tuscany
Exterior
Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena

Vico dʼArbia
The price is SAR 5,537
SAR 5,970 total
includes taxes & fees
10 Dec - 11 Dec
Villa Torre Among the Hills of Siena
Exterior
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR
The price is SAR 4,999
SAR 5,283 total
includes taxes & fees
8 Dec - 9 Dec
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Exterior
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

Roccastrada GR
The price is SAR 4,999
SAR 5,283 total
includes taxes & fees
8 Dec - 9 Dec
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Exterior
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR
The price is SAR 4,999
SAR 5,283 total
includes taxes & fees
8 Dec - 9 Dec
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Outdoor dining
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Vico dʼArbia
The price is SAR 3,775
SAR 4,208 total
includes taxes & fees
8 Dec - 9 Dec
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
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
"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"
Phil 1-night trip
Posted 3 days ago
Hotel Italia

Frequently asked questions

How much do villas in Castiglione del Bosco cost?
Rates for villas in Castiglione del Bosco range between SAR 618 and SAR 31,768 per night. Whatever your budget, you can find a place that fits the bill on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Castiglione del Bosco?
Pack your suitcase and pick from 535 villas in Castiglione del Bosco. For a family escape, a getaway with pals and everything in between, Expedia can help you find the right place in a few simple clicks.
Why book your villa in Castiglione del Bosco with Expedia?
Reserving a villa in Castiglione del Bosco is as easy as entering your travel dates and picking the option that has what you need. Searching for something luxurious or low cost, or a stay that also includes free WiFi? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Castiglione del Bosco?
With Expedia's user-friendly filter tool, locating cheap villas in Castiglione del Bosco is a cinch. To discover properties that'll make your wallet smile, refine your search results by budget, amenities and star rating.

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