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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 NZ$253
includes taxes & fees
3 Nov - 4 Nov
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 NZ$296
includes taxes & fees
7 Oct - 8 Oct
Borgo Dolciano
A bakery display with various pastries and desserts.

3. 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 NZ$224
includes taxes & fees
10 Oct - 11 Oct
La Piccola Locanda
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

4. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (19 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is NZ$147
includes taxes & fees
25 Oct - 26 Oct
FonteLiving
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

5. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is NZ$890
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.

6. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (159 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is NZ$293
includes taxes & fees
28 Oct - 29 Oct
Hotel San Gregorio
A poolside area with two glasses of water, candles, and a stone pathway.

7. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (99 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 NZ$354
includes taxes & fees
30 Oct - 31 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.

8. 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 NZ$167
includes taxes & fees
5 Nov - 6 Nov
TuscanyLettings Studio&Room
Front of property

9. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is NZ$230
includes taxes & fees
7 Oct - 8 Oct
montorio
An arched doorway leading to a building with a wooden door and a staircase.

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (111 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 NZ$158
includes taxes & fees
14 Oct - 15 Oct
Residenza Fabroni
A terrace with a table set for breakfast, overlooking a scenic landscape.

11. 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 NZ$344
includes taxes & fees
6 Oct - 7 Oct
Delcorto Suites
A historic building with a tower, a courtyard, and a well-lit entrance.

12. 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 NZ$212
includes taxes & fees
5 Nov - 6 Nov
Abbadia Sicille Relais
An interior courtyard with stone columns, arches, and a mosaic.

13. 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 NZ$303
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".

14. 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 NZ$215
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
A crowded restaurant with brick walls and multiple tables and chairs.

15. 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 NZ$377
includes taxes & fees
17 Oct - 18 Oct
La Locanda di San Francesco
An outdoor dining area with a rustic brick oven, a wooden table set with plates, glasses, and a bowl of fruit.

16. Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi

Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi
Chianciano Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: Todo nos gustó. Las vistas, el departamento impecable,limpio. Tranquilo. El desayuno espectacular. Está alejado de la ciudad como para desconectar y relajarse disfrutando de las vistas y el atardecer. Cons: Nada"
Spain
Anonymous traveller
The price is NZ$517
includes taxes & fees
15 Oct - 16 Oct
Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi
A modern kitchen with a round dining table, black cabinetry, and a large clock on the wall.

17. Affittacamere I Canneggiatori

Affittacamere I Canneggiatori
Abbadia San Salvatore
8.6 out of 10, Excellent, (9 reviews)
"Very stylish, modern, well equipped apartment. Close to everything. Bed is okay, had a relaxing sleep. Good size bathroom with toilet. Staff who came to clean daily was very helpful, supportive, kind. Parking on the street in from of the building. "
United Kingdom
Erika
The price is NZ$131
includes taxes & fees
7 Oct - 8 Oct
Affittacamere I Canneggiatori
A stone building with a wooden door, a staircase, and a small window with a metal grill.

18. 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 NZ$185
includes taxes & fees
5 Nov - 6 Nov
Casa Gioia - Casa Olivieri
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

19. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is NZ$245
includes taxes & fees
19 Oct - 20 Oct
"Il Focolare" Superior Apartment in Monticchiello
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

20. 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 NZ$247
includes taxes & fees
2 Nov - 3 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
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

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"A beautiful, luxury estate in the countryside. While we traveled as a couple, it seemed a popular destination for families with children. The restaurant on site was excellent and the rooms were well appointed and comfortable. We stayed in a junior suite which had stairs from the living room/bathroom up to the bedroom loft. *something to be aware of when booking"
Elizabeth 3-night trip
Posted 13 hours ago
Precise Tale Poggio Alla Sala

Find out more about Castiglioncello del Trinoro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Castiglioncello del Trinoro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Castiglioncello del Trinoro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Castiglioncello del Trinoro. Seeing all the best attractions is bound to make you fall in love with Castiglioncello del Trinoro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Castiglioncello del Trinoro short-term rentals, that won’t be hard to do.

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 are some of the best holiday rentals that Castiglioncello del Trinoro has to offer?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This holiday home rental outside of Castiglioncello del Trinoro is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.