Default HTG hotel image

Castiglioncello del Trinoro Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Castiglioncello del Trinoro 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, (69 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ￥15,289
￥21,231 total
includes taxes & fees
Nov 6 - Nov 7
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 ￥23,466
￥26,166 total
includes taxes & fees
Oct 7 - Oct 8
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 ￥17,832
￥20,324 total
includes taxes & fees
Oct 7 - Oct 8
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, (26 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ￥70,875
￥78,672 total
includes taxes & fees
Nov 2 - Nov 3
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, (159 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ￥20,555
￥23,674 total
includes taxes & fees
Nov 6 - Nov 7
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, (19 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is ￥11,452
￥12,951 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥36,533
￥40,896 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥18,822
￥21,058 total
includes taxes & fees
Oct 9 - Oct 10
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 ￥23,734
￥26,816 total
includes taxes & fees
Oct 8 - Oct 9
Meublé Il Riccio
A bedroom with a large bed, a wardrobe, a bench, and a nightstand.

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 ￥16,672
￥19,048 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥29,234
￥32,868 total
includes taxes & fees
Oct 17 - Oct 18
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 ￥12,076
￥13,994 total
includes taxes & fees
Oct 14 - Oct 15
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 ￥30,009
￥33,720 total
includes taxes & fees
Oct 22 - Oct 23
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, (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 ￥26,520
￥29,883 total
includes taxes & fees
Oct 30 - Oct 31
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 ￥16,353
￥18,521 total
includes taxes & fees
Nov 5 - Nov 6
Abbadia Sicille Relais
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 traveler
The price is ￥31,008
￥45,714 total
includes taxes & fees
Oct 15 - Oct 16
Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

17. 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 ￥12,525
￥14,487 total
includes taxes & fees
Nov 5 - Nov 6
TuscanyLettings Studio&Room
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

18. "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 ￥17,719
￥21,617 total
includes taxes & fees
Oct 19 - Oct 20
"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.

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 ￥19,168
￥21,794 total
includes taxes & fees
Nov 2 - Nov 3
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.

20. 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 ￥12,779
￥14,766 total
includes taxes & fees
Nov 2 - Nov 3
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 20 hours ago
Mastrojanni Relais - Small Luxury Hotels of the World

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:

  • View our selection of featured holiday rentals in Castiglioncello del Trinoro
  • Use the map to find apartments and other holiday homes in the Castiglioncello del Trinoro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castiglioncello del Trinoro while they last

Look no further and take a look at our great range of rental properties in Castiglioncello del Trinoro!

Frequently asked questions

Can I find a vacation rental in Castiglioncello del Trinoro?

Yes, we have vacation rentals near top points of interest in Castiglioncello del Trinoro, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Castiglioncello del Trinoro?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental outside of Castiglioncello del Trinoro is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 larger area.

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

A vacation rental is a private property you can stay in for a few weeks or just a few days in Castiglioncello del Trinoro. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.