Castiglione d'Orcia Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Castiglione d'Orcia vacation rentals

Fridge, microwave, oven, stovetop
'...a delicious farmhouse in the countryside where only the wind blows...'

Villa in Campiglia d'Orcia

'...a delicious farmhouse in the countryside where only the wind blows...'
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 ￥174,491
￥284,696 total
includes taxes & fees
Jan 5 - Jan 6, 2026
'...a delicious farmhouse in the countryside where only the wind blows...'
Property grounds
Bad and Breakfast La Balena Bianca House

Apartment in Bagni San Filippo

Bad and Breakfast La Balena Bianca House
The price is ￥18,367
￥25,163 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Bad and Breakfast La Balena Bianca House
Exterior detail
Independent house in the historic center

Vacation Home in CASTIGLIONE D'ORCIA

Independent house in the historic center
9.4 out of 10, Exceptional, (9)
"Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! "
United Kingdom
Graham S.
The price is ￥26,449
￥31,225 total
includes taxes & fees
Dec 26 - Dec 27
Independent house in the historic center
Property grounds
Ambrosia Room Fonte Alle Ninfe Bed and Breakfast

Apartment in Castiglione dʼOrcia

Ambrosia Room Fonte Alle Ninfe Bed and Breakfast
The price is ￥19,837
￥20,572 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Ambrosia Room Fonte Alle Ninfe Bed and Breakfast
Outdoor dining
Ermione seen on the Val d'Orcia

Vacation Home in Castiglione d'Orcia

Ermione seen on the Val d'Orcia
8.8 out of 10, Excellent, (3)
"Alles top"
Germany
ANDREAS ALEXANDER
The price is ￥24,796
￥34,935 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Ermione seen on the Val d'Orcia
Outdoor dining
Room 'L'imbrunire - Il Lampadone' with Shared Garden, Wi-Fi and Air Conditioning

Apartment in Campiglia D'Orcia

Room 'L'imbrunire - Il Lampadone' with Shared Garden, Wi-Fi and Air Conditioning
The price is ￥27,551
￥28,286 total
includes taxes & fees
Dec 27 - Dec 28
Room 'L'imbrunire - Il Lampadone' with Shared Garden, Wi-Fi and Air Conditioning
Outdoor dining
Apartment 'La Balena Rosa' with Private Terrace and Wi-Fi

Apartment in Bagni San Filippo

Apartment 'La Balena Rosa' with Private Terrace and Wi-Fi
The price is ￥44,800
￥51,135 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Apartment 'La Balena Rosa' with Private Terrace and Wi-Fi
1 bedroom, WiFi, bed sheets
Cirene Room Fonte Alle Ninfe Bed and Breakfast

Apartment in Castiglione dʼOrcia

Cirene Room Fonte Alle Ninfe Bed and Breakfast
The price is ￥19,837
￥20,572 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Cirene Room Fonte Alle Ninfe Bed and Breakfast
Outdoor dining
Room 'Il Castellare' with Shared Garden, Wi-Fi and Air Conditioning

Apartment in Campiglia D'Orcia

Room 'Il Castellare' with Shared Garden, Wi-Fi and Air Conditioning
The price is ￥29,388
￥30,123 total
includes taxes & fees
Dec 27 - Dec 28
Room 'Il Castellare' with Shared Garden, Wi-Fi and Air Conditioning
Outdoor dining
Room 'Il Cannellone' with Shared Garden and Wi-Fi

Apartment in Campiglia D'Orcia

Room 'Il Cannellone' with Shared Garden and Wi-Fi
The price is ￥27,919
￥28,654 total
includes taxes & fees
Dec 28 - Dec 29
Room 'Il Cannellone' with Shared Garden and Wi-Fi
Outdoor dining
Room 'L'imbrunire - L'opificio' with Shared Garden, Wi-Fi and Air Conditioning

Apartment in Campiglia D'Orcia

Room 'L'imbrunire - L'opificio' with Shared Garden, Wi-Fi and Air Conditioning
The price is ￥32,143
￥32,878 total
includes taxes & fees
Dec 26 - Dec 27
Room 'L'imbrunire - L'opificio' with Shared Garden, Wi-Fi and Air Conditioning
Outdoor dining
Room 'Il Teatro' with Shared Garden, Wi-Fi and Air Conditioning

Apartment in Campiglia D'Orcia

Room 'Il Teatro' with Shared Garden, Wi-Fi and Air Conditioning
The price is ￥32,143
￥32,878 total
includes taxes & fees
Dec 26 - Dec 27
Room 'Il Teatro' with Shared Garden, Wi-Fi and Air Conditioning
Property grounds
Dafne Room - Fonte Alle Ninfe Bed and Breakfast

Apartment in Castiglione dʼOrcia

Dafne Room - Fonte Alle Ninfe Bed and Breakfast
The price is ￥38,021
￥38,756 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Dafne Room - Fonte Alle Ninfe Bed and Breakfast
Bar (on property)
La Piccola Locanda

Townhouse in Chiusi

La Piccola Locanda
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda
Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers
FonteLiving

Townhouse in San Casciano dei Bagni

FonteLiving
10.0 out of 10, Exceptional, (5)
"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."
United Kingdom
R
The price is ￥11,754
￥13,297 total
includes taxes & fees
Dec 26 - Dec 27
FonteLiving
Pillowtop beds, minibar, in-room safe, individually decorated
La Locanda Di Cetona

Townhouse in Cetona

La Locanda Di Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona
View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥10,507
￥12,109 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Abbadia Sicille Relais
Seasonal outdoor pool, open 8:30 AM to 8:00 PM, pool umbrellas
Villaggio Le Querce

Residence in Sorano

Villaggio Le Querce
4.0 star property
9.0 out of 10, Wonderful, (57)
"Nice neighborhood with Sorano close by. No restaurant or bar open. Lack of bedsheets and towels for 3 people. The shower head was too heavy to stay in the shower head holder"
Finland
Åsa
The price is ￥14,727
￥17,118 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Villaggio Le Querce
Double Room | Balcony
Il Cantuccio

Townhouse in Manciano

Il Cantuccio
9.2 out of 10, Wonderful, (53)
"very warm and welcoming. I do recommend having a phone with roaming access so you can receive your instructions to access."
Australia
Eugenio
Il Cantuccio
Exterior
La Dimora di Dida

Residence in Seggiano

La Dimora di Dida
The price is ￥11,522
￥12,674 total
includes taxes & fees
Jan 25 - Jan 26, 2026
La Dimora di Dida
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castiglione d'Orcia Hotel Reviews

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 3 weeks ago
Abbadia Sicille Relais

Find out more about Castiglione d'Orcia

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

  • View our selection of featured holiday rentals in Castiglione d'Orcia
  • Use the map to find apartments and other holiday homes in the Castiglione d'Orcia neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castiglione d'Orcia while they last

Look no further and take a look at our great range of rental properties in Castiglione d'Orcia!

Frequently asked questions

Are there vacation rentals in Castiglione d'Orcia?

Yes, there are vacation rentals close to well known sights in Castiglione d'Orcia, or you can select a secluded option if you want a relaxing place to stay. Castiglione d'Orcia is known for its hot springs and spas. Make sure you have time to check out the riverfront while you're in the area.

What are some of the best vacation home rentals in Castiglione d'Orcia?

The House of Alice, charm and relaxation: Visitors like this Castiglione d'Orcia vacation home rental. It is located in a rural location and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Castiglione d'Orcia?

Choose from 29 Expedia vacation rentals in Castiglione d'Orcia for a memorable vacation.

What’s there to see and do in Castiglione d'Orcia?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like Historic Centre of Pienza. While here, Baths of San Filippo and Valdorcia Terre Senesi are other places worth a visit.

What’s a vacation rental in Castiglione d'Orcia like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Castiglione d'Orcia. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips.