A historic town with stone buildings, a prominent castle on a hill, and snow-capped mountains in the background.

Castiglione d'Orcia Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Castiglione d'Orcia vacation rentals

A patio area with outdoor seating, potted plants, and a view of the landscape.

1. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is P6,913
P9,380 total
includes taxes & fees
Oct 7 - Oct 8
Affitacamere Maria Gabriella
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

2. 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 P8,340
P9,462 total
includes taxes & fees
Sep 30 - Oct 1
B&B Le Scalette di Piazza
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

3. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (157 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is P12,309
P13,968 total
includes taxes & fees
Oct 4 - Oct 5
Hotel San Gregorio
An interior courtyard with stone columns, arches, and a mosaic.

4. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is P10,160
P11,462 total
includes taxes & fees
Oct 11 - Oct 12
Meublé Il Riccio
A stone archway leading to a dining area with a table set for two, overlooking a lush green landscape.

5. Agriturismo Poggio Monte

Agriturismo Poggio Monte
Manciano
9.8 out of 10, Exceptional, (14 reviews)
" Great place and staff"
United States
Tomas
The price is P6,709
P7,594 total
includes taxes & fees
Sep 30 - Oct 1
Agriturismo Poggio Monte
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

6. 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 P11,000
P12,387 total
includes taxes & fees
Oct 21 - Oct 22
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

7. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is P8,386
P9,509 total
includes taxes & fees
Oct 25 - Oct 26
Bed & Breakfast Vicolo dell'Oste
A crowded restaurant with brick walls and multiple tables and chairs.

8. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (148 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is P13,249
P14,861 total
includes taxes & fees
Sep 27 - Sep 28
La Locanda di San Francesco
An arched doorway leading to a building with a wooden door and a staircase.

9. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (110 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 P6,300
P7,216 total
includes taxes & fees
Oct 13 - Oct 14
Residenza Fabroni
A poolside area with two glasses of water, candles, and a stone pathway.

10. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (96 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is P10,838
P12,207 total
includes taxes & fees
Oct 13 - Oct 14
Casanova - Panoramic Rooms and Suites
A historic building with a tower, a courtyard, and a well-lit entrance.

11. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is P7,759
P8,749 total
includes taxes & fees
Oct 25 - Oct 26
Abbadia Sicille Relais
A stone building with a balcony, a small table, and chairs.

12. Dimora dei Magi

Dimora dei Magi
Saturnia
9.2 out of 10, Wonderful, (9 reviews)
"Nice place"
United States
Nicki
The price is P4,200
P4,620 total
includes taxes & fees
Sep 30 - Oct 1
Dimora dei Magi
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

13. 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 P5,615
P6,751 total
includes taxes & fees
Oct 11 - Oct 12
Idolina Guest House
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

14. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is P6,429
P7,357 total
includes taxes & fees
Oct 25 - Oct 26
PienzaLettings Suites
A natural hot spring with multiple pools and people swimming.

15. Il Cantuccio

Il Cantuccio
Manciano
9.2 out of 10, Wonderful, (62 reviews)
"very warm and welcoming. I do recommend having a phone with roaming access so you can receive your instructions to access."
Australia
Eugenio
The price is P4,882
P5,584 total
includes taxes & fees
Oct 23 - Oct 24
Il Cantuccio
A terrace with a table set for breakfast, overlooking a scenic landscape.

16. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (44 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is P12,076
P13,569 total
includes taxes & fees
Oct 8 - Oct 9
Delcorto Suites
A bakery display with various pastries and desserts.

17. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is P7,574
P8,474 total
includes taxes & fees
Oct 23 - Oct 24
La Piccola Locanda
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

18. 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 P7,056
P8,047 total
includes taxes & fees
Oct 15 - Oct 16
TuscanyLettings Studio&Room
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

19. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (16 reviews)
"We absolutely loved staying here - the location was very central in Tuscany, it was a beautiful property with a lovely view and a very nice pool area. The staff was amazing and the value was incredible. We would definitely stay here again."
United States
Davide
The price is P10,332
P11,935 total
includes taxes & fees
Oct 18 - Oct 19
Corte Francigena - Apartments
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

20. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (131 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is P22,346
P24,865 total
includes taxes & fees
Oct 3 - Oct 4
Il Tosco
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 d'Orcia Hotel Reviews

Castello di Leonina Relais

Castello di Leonina Relais

10/10 Excellent
"Amazing"
Glen 2-night trip
Posted 16 hours ago
Castello di Leonina 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:

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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.

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

Choose from 35 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.