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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Castiglioncello del Trinoro holiday rentals

A garden with two chairs under trees, a table, and a view of the landscape.

1. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (75 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ฿3,632
฿4,927 total
includes taxes & fees
13 Nov - 14 Nov
Affitacamere Maria Gabriella
A swimming pool with two lounge chairs and a table, surrounded by a well-maintained lawn.

2. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (22 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is ฿2,728
฿3,075 total
includes taxes & fees
18 Nov - 19 Nov
FonteLiving
An outdoor dining area with tables and chairs, a covered patio, and a building labeled "RISTORANTE".

3. La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.0 out of 10, Wonderful, (9 reviews)
"It was such a lovely experience. Bang in the centre of the town, still very quiet. The room was breathtaking, lovely breakfast (generosity though depended on staff). Overall such a great experience I would go back today!"
United Kingdom
GianPaolo
The price is ฿4,597
฿5,056 total
includes taxes & fees
4 Dec - 5 Dec
La Locanda Di Cetona
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (171 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is ฿4,597
฿5,282 total
includes taxes & fees
16 Nov - 17 Nov
Hotel San Gregorio
An outdoor dining table with a meal consisting of bread, tomatoes, and cured meat, accompanied by a glass of white wine.

5. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 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 ฿4,903
฿5,544 total
includes taxes & fees
26 Nov - 27 Nov
La Locanda di San Francesco
An interior courtyard with stone columns, arches, and a mosaic.

6. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (122 reviews)
"The room was beautifully designed, clean and fresh with stunning views in a truly historic building. Family run and a special experience!!"
United States
Slimane
The price is ฿5,338
฿6,021 total
includes taxes & fees
19 Nov - 20 Nov
Meublé Il Riccio
A bakery display with various pastries and desserts.

7. 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 ฿3,979
฿4,452 total
includes taxes & fees
21 Nov - 22 Nov
La Piccola Locanda
A historic building with a tower, a courtyard, and a well-lit entrance.

8. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is ฿2,176
฿2,506 total
includes taxes & fees
26 Nov - 27 Nov
Abbadia Sicille Relais
A terrace with a table set for breakfast, overlooking a scenic landscape.

9. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ฿5,709
฿6,430 total
includes taxes & fees
14 Nov - 15 Nov
Delcorto Suites
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

10. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is ฿3,172
฿3,639 total
includes taxes & fees
15 Nov - 16 Nov
Bed & Breakfast Vicolo dell'Oste
An arched doorway leading to a building with a wooden door and a staircase.

11. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (117 reviews)
"Was a very nice spot"
Canada
Andrew
The price is ฿3,003
฿3,454 total
includes taxes & fees
18 Nov - 19 Nov
Residenza Fabroni
A stone building with a tiled roof, surrounded by tall trees and a gravel path.

12. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (12 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is ฿4,015
฿4,566 total
includes taxes & fees
13 Nov - 14 Nov
montorio
A pool area with lounge chairs and umbrellas, surrounded by tall cypress trees and a view of distant hills.

13. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (105 reviews)
"Hotel had beautiful views and amenities like breakfast and spa were amazing."
United States
Oscar
The price is ฿5,993
฿6,742 total
includes taxes & fees
24 Nov - 25 Nov
Casanova - Panoramic Rooms and Suites
A stone building with a courtyard, outdoor seating, and a warm light setting.

14. 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 ฿3,712
฿4,532 total
includes taxes & fees
26 Nov - 27 Nov
Sarna Residence
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

15. 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 ฿2,942
฿3,386 total
includes taxes & fees
9 Dec - 10 Dec
TuscanyLettings Studio&Room
A narrow cobblestone street with a rustic building featuring a brick archway and ivy-covered walls. There is a wooden chair and a table with a checkered tablecloth outside.

16. 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 ฿3,083
฿3,542 total
includes taxes & fees
26 Nov - 27 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

17. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (141 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is ฿7,723
฿8,645 total
includes taxes & fees
25 Nov - 26 Nov
Il Tosco
A bedroom with a bed, a nightstand, a painting, and a view of the upper floor.

18. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (7 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ฿2,844
฿3,278 total
includes taxes & fees
10 Dec - 11 Dec
PienzaLettings Suites
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 Castiglioncello del Trinoro Hotel Reviews

L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"This was a wonderful stay. Bagno Vignoni and the surrounding area are truly magical and i absolutely loved staying at Orto Le Terme - this is one of those instances where the room photos did not do it justice. I loved the room - it felt warm and inviting with supremely tasteful decor and a big comfortable bathroom with separate shower and freestanding bath. The breakfasts were next level. I think one of the best hotel breakfasts i've had. Lots of amazing local Tuscan produce. Cannot recommend enough."
Pat 4-night trip
Posted 1 day ago
L'Orto delle Terme

Find out more about Castiglioncello del Trinoro

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

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Frequently asked questions

Can I find a holiday rental in Castiglioncello del Trinoro?

Yes, there are holiday rentals close to the most popular sights in Castiglioncello del Trinoro, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Castiglioncello del Trinoro?

While exploring the area, visit family-friendly sights like Pasticceria Il Campanile, or get outside and enjoy nature at La Foce. Terme di Chianciano and Piscine Termali Theia are a couple of places you'll find in the wider area.

What’s a holiday rental in Castiglioncello del Trinoro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castiglioncello del Trinoro. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for families.