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Castiglioncello del Trinoro Vacation Rentals

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Our top choices for Castiglioncello del Trinoro vacation rentals

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 CA $299
CA $335 total
includes taxes & fees
Oct 12 - Oct 13
La Locanda di San Francesco

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 CA $147
CA $202 total
includes taxes & fees
Oct 7 - Oct 8
Affitacamere Maria Gabriella

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 CA $174
CA $198 total
includes taxes & fees
Oct 14 - Oct 15
Bed & Breakfast Vicolo dell'Oste

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 CA $220
CA $249 total
includes taxes & fees
Oct 12 - Oct 13
Meublé Il Riccio

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 CA $159
CA $178 total
includes taxes & fees
Sep 30 - Oct 1
La Piccola Locanda

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 CA $273
CA $307 total
includes taxes & fees
Oct 6 - Oct 7
Delcorto Suites

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 CA $205
CA $235 total
includes taxes & fees
Oct 28 - Oct 29
Hotel San Gregorio

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 CA $113
CA $131 total
includes taxes & fees
Oct 19 - Oct 20
Residenza Fabroni

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 CA $104
CA $118 total
includes taxes & fees
Oct 25 - Oct 26
FonteLiving

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 CA $163
CA $184 total
includes taxes & fees
Oct 28 - Oct 29
Abbadia Sicille Relais

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 CA $227
CA $253 total
includes taxes & fees
Sep 29 - Sep 30
Borgo Dolciano

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 CA $505
CA $562 total
includes taxes & fees
Oct 3 - Oct 4
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 CA $162
CA $185 total
includes taxes & fees
Oct 5 - Oct 6
montorio

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 CA $187
CA $212 total
includes taxes & fees
Oct 7 - Oct 8
B&B Le Scalette di Piazza

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 CA $258
CA $290 total
includes taxes & fees
Oct 4 - Oct 5
Casanova - Panoramic Rooms and Suites

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 CA $139
CA $159 total
includes taxes & fees
Oct 28 - Oct 29
TuscanyLettings Studio&Room

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 CA $123
CA $142 total
includes taxes & fees
Sep 30 - Oct 1
Residence al Lago

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 CA $137
CA $157 total
includes taxes & fees
Oct 25 - Oct 26
PienzaLettings Suites

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 CA $212
CA $239 total
includes taxes & fees
Oct 1 - Oct 2
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

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 CA $144
CA $164 total
includes taxes & fees
Oct 14 - Oct 15
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

Find out more about Castiglioncello del Trinoro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.