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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Castiglioncello del Trinoro holiday rentals

A crowded restaurant with brick walls and multiple tables and chairs.

1. 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 ฿7,053
฿7,910 total
includes taxes & fees
12 Oct - 13 Oct
La Locanda di San Francesco
A patio area with outdoor seating, potted plants, and a view of the landscape.

2. 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 ฿3,687
฿5,003 total
includes taxes & fees
12 Oct - 13 Oct
Affitacamere Maria Gabriella
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

3. 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 ฿4,115
฿4,679 total
includes taxes & fees
22 Oct - 23 Oct
Bed & Breakfast Vicolo dell'Oste
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 ฿5,419
฿6,113 total
includes taxes & fees
1 Oct - 2 Oct
Meublé Il Riccio
A bakery display with various pastries and desserts.

5. 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 ฿4,040
฿4,520 total
includes taxes & fees
29 Sept - 30 Sept
La Piccola Locanda
A terrace with a table set for breakfast, overlooking a scenic landscape.

6. 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 ฿6,441
฿7,237 total
includes taxes & fees
6 Oct - 7 Oct
Delcorto Suites
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

7. 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 ฿4,841
฿5,553 total
includes taxes & fees
28 Oct - 29 Oct
Hotel San Gregorio
An arched doorway leading to a building with a wooden door and a staircase.

8. 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 ฿2,671
฿3,090 total
includes taxes & fees
19 Oct - 20 Oct
Residenza Fabroni
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

9. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (17 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is ฿2,458
฿2,780 total
includes taxes & fees
25 Oct - 26 Oct
FonteLiving
A historic building with a tower, a courtyard, and a well-lit entrance.

10. 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 ฿4,138
฿4,666 total
includes taxes & fees
25 Oct - 26 Oct
Abbadia Sicille Relais
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

11. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is ฿5,368
฿5,980 total
includes taxes & fees
29 Sept - 30 Sept
Borgo Dolciano
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

12. 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 ฿10,978
฿12,228 total
includes taxes & fees
5 Oct - 6 Oct
Il Tosco

13. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is ฿3,827
฿4,362 total
includes taxes & fees
5 Oct - 6 Oct
montorio
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

14. 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 ฿4,418
฿5,012 total
includes taxes & fees
7 Oct - 8 Oct
B&B Le Scalette di Piazza
A poolside area with two glasses of water, candles, and a stone pathway.

15. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (97 reviews)
"The room snd entire property were spotless clean. Staff wete helpful and friendly. Our room and patio overlooked the d'Orcia valley, gorgeous any time, especially in the morning. The entire grounds, pool, loungers, plants were well maintained. This was our third time at Cassanova and we would come again. A short walk into San Quirico d'Orcia with several good restaurants and a COOP store for drinks and groceries."
Canada
Zoltan
The price is ฿6,085
฿6,845 total
includes taxes & fees
4 Oct - 5 Oct
Casanova - Panoramic Rooms and Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

16. 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 ฿3,764
฿4,292 total
includes taxes & fees
18 Oct - 19 Oct
TuscanyLettings Studio&Room
A fountain with water cascading down a column, surrounded by greenery and a building in the background.

17. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is ฿3,120
฿3,584 total
includes taxes & fees
29 Sept - 30 Sept
Residence al Lago
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

18. 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 ฿3,429
฿3,924 total
includes taxes & fees
25 Oct - 26 Oct
PienzaLettings Suites
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

19. 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 ฿5,413
฿6,106 total
includes taxes & fees
26 Oct - 27 Oct
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A stone building with a wooden door, a staircase, and a small window with a metal grill.

20. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is ฿3,851
฿4,388 total
includes taxes & fees
12 Oct - 13 Oct
Casa Gioia - Casa Olivieri
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

Nuovo Etruria Resort

Nuovo Etruria Resort

8/10 Good
"very nice place to stay. wonderful view of Montepulciano. nice amenities and breakfast. The only issue was we stayed in the furthest building from the main house and Wi-Fi was limited. good location as a base to travel through Tuscany."
Louis 4-night trip
Posted 18 hours ago
Nuovo Etruria Resort

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.