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Castiglioncello del Trinoro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Castiglioncello del Trinoro vacation rentals

A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

1. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (21 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
$74 nightly
The price is $84
Oct 30 - Oct 31
Total with taxes and fees
FonteLiving
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, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$117 nightly
The price is $133
Oct 28 - Oct 29
Total with taxes and fees
Affitacamere Maria Gabriella
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
$110 nightly
The price is $123
Oct 24 - Oct 25
Total with taxes and fees
La Piccola Locanda
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

4. 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
$149 nightly
The price is $166
Oct 22 - Oct 23
Total with taxes and fees
Borgo Dolciano
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

5. 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
$85 nightly
The price is $98
Nov 4 - Nov 5
Total with taxes and fees
TuscanyLettings Studio&Room
An arched doorway leading to a building with a wooden door and a staircase.

6. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (114 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
$91 nightly
The price is $104
Nov 3 - Nov 4
Total with taxes and fees
Residenza Fabroni
Front of property

7. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful place, view and city."
United States
Federico
$113 nightly
The price is $129
Oct 22 - Oct 23
Total with taxes and fees
montorio
A stone building with a wooden door, a staircase, and a small window with a metal grill.

8. 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
$107 nightly
The price is $122
Oct 29 - Oct 30
Total with taxes and fees
Casa Gioia - Casa Olivieri
A historic building with a tower, a courtyard, and a well-lit entrance.

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
$87 nightly
The price is $99
Nov 17 - Nov 18
Total with taxes and fees
Abbadia Sicille Relais
A bedroom with a bed, a TV, a wardrobe, and a view of a garden.

10. Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
$85 nightly
The price is $104
Oct 23 - Oct 24
Total with taxes and fees
Boutique Apartment Natura
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

11. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (166 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
$134 nightly
The price is $154
Nov 9 - Nov 10
Total with taxes and fees
Hotel San Gregorio
A view through a glass door into a patio area with a white chair, a table, and a banner advertising a boutique hotel.

12. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
$85 nightly
The price is $104
Oct 23 - Oct 24
Total with taxes and fees
Boutique Apartment Eleganza
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

13. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (6 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
$81 nightly
The price is $94
Nov 2 - Nov 3
Total with taxes and fees
PienzaLettings Suites
A stone building with a courtyard, outdoor seating, and a warm light setting.

14. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
$111 nightly
The price is $126
Nov 18 - Nov 19
Total with taxes and fees
Sarna Residence
A stone building with a wooden door, steps leading to a balcony, and potted plants.

15. The Old Washhouse

The Old Washhouse
Radicofani
10.0 out of 10, Exceptional, (2 reviews)
"What a wonderful stay! This apartment was absolutely perfect for the two of us. It was impeccably clean, warm, cozy, and spacious enough for a couple. The bed and furniture was so comfortable, and the attention to detail was simply spot on. Everything was absolutely perfect!We were so touched by the thoughtful complimentary coffee, tea, and breakfast items. The bathroom was just as equipped with shampoo and soaps. Every little detail made us feel right at home.The gorgeous private garden was a...
Canada
Chantale M.
$145 nightly
The price is $149
Oct 26 - Oct 27
Total with taxes and fees
The Old Washhouse
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

16. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 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
$106 nightly
The price is $121
Nov 13 - Nov 14
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste
A room with a curved ceiling, a hot tub, and a glass door leading outside.

17. Chalet Il Cristallo

Chalet Il Cristallo
Castel del Piano
7.6 out of 10, Good, (4 reviews)
"Camera impeccabile, personale cortese e disponibile, colazione ottima ,come la cena. Struttura molto accogliente. Ottima per famiglie."
Italy
Federico
$45 nightly
The price is $52
Oct 27 - Oct 28
Total with taxes and fees
Chalet Il Cristallo
A stone building with a tiled roof, a staircase leading to a lower level, and a garden with various plants.

18. Double bedroom with private bathroom, private access, garden and swimming pool

Double bedroom with private bathroom, private access, garden and swimming pool
Radicofani
$90 nightly
The price is $94
Nov 2 - Nov 3
Total with taxes and fees
Double bedroom with private bathroom, private access, garden and swimming pool
A stone building with a wooden door and shutters, a small outdoor seating area with a table and chairs, and potted plants.

19. Federico's Cantuccio, cozy apartment in the heart of Radicofani

Federico's Cantuccio, cozy apartment in the heart of Radicofani
Radicofani
$101 nightly
The price is $105
Nov 1 - Nov 2
Total with taxes and fees
Federico's Cantuccio, cozy apartment in the heart of Radicofani
An outdoor dining area with a rustic brick oven, a wooden table set with plates, glasses, and a bowl of fruit.

20. 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
$266 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi
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

Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Nice hotel in a great location, very close to Pienza’s historic center. The room was clean, and the staff were helpful. Breakfast could be improved, particularly in terms of the variety of hot food available. The daily parking fee was also somewhat expensive."
Ramon 4-night trip
Posted 7 hours ago
Hotel San Gregorio

Find out more about Castiglioncello del Trinoro

Everything you need to know about Castiglioncello del Trinoro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglioncello del Trinoro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglioncello del Trinoro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castiglioncello del Trinoro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglioncello del Trinoro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castiglioncello del Trinoro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castiglioncello del Trinoro rentals

At Expedia, we put the best Castiglioncello del Trinoro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castiglioncello del Trinoro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglioncello del Trinoro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglioncello del Trinoro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.