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Castiglioncello del Trinoro Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Castiglioncello del Trinoro holiday 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, (69 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is S$174
includes taxes & fees
13 Oct - 14 Oct
Affitacamere Maria Gabriella
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

2. 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 S$198
includes taxes & fees
8 Oct - 9 Oct
Borgo Dolciano
Front of property

3. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is S$165
includes taxes & fees
19 Oct - 20 Oct
montorio
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

4. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (27 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is S$639
includes taxes & fees
2 Nov - 3 Nov
L'Olmo
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

5. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (160 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is S$206
includes taxes & fees
6 Nov - 7 Nov
Hotel San Gregorio
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

6. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (20 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is S$105
includes taxes & fees
25 Oct - 26 Oct
FonteLiving
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

7. 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 S$332
includes taxes & fees
2 Nov - 3 Nov
Il Tosco
A bakery display with various pastries and desserts.

8. 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 S$171
includes taxes & fees
8 Oct - 9 Oct
La Piccola Locanda
An interior courtyard with stone columns, arches, and a mosaic.

9. 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 S$218
includes taxes & fees
8 Oct - 9 Oct
Meublé Il Riccio
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, (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 S$155
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
A crowded restaurant with brick walls and multiple tables and chairs.

11. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (149 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 S$249
includes taxes & fees
7 Nov - 8 Nov
La Locanda di San Francesco
An arched doorway leading to a building with a wooden door and a staircase.

12. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (112 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 S$111
includes taxes & fees
9 Oct - 10 Oct
Residenza Fabroni
A terrace with a table set for breakfast, overlooking a scenic landscape.

13. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (46 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is S$274
includes taxes & fees
22 Oct - 23 Oct
Delcorto Suites
A poolside area with two glasses of water, candles, and a stone pathway.

14. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is S$242
includes taxes & fees
30 Oct - 31 Oct
Casanova - Panoramic Rooms and Suites
A historic building with a tower, a courtyard, and a well-lit entrance.

15. 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 S$160
includes taxes & fees
2 Nov - 3 Nov
Abbadia Sicille Relais
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 S$113
includes taxes & fees
5 Nov - 6 Nov
TuscanyLettings Studio&Room
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

17. 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 S$177
includes taxes & fees
2 Nov - 3 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
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 S$120
includes taxes & fees
2 Nov - 3 Nov
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

Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World

10/10 Excellent
"Such a beautiful location and very helpful staff. The hotel and winery were amazing!"
Frank 2-night trip
Posted 2 days ago
Mastrojanni Relais - Small Luxury Hotels of the World

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.