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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Castiglioncello del Trinoro vacation homes

Exterior
Agriturismo San Filippo

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
9.0 out of 10, Wonderful, (13)
"Excellent experience!"
United States
Richard
Agriturismo San Filippo
Interior entrance
Poggio del Sole

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very Good, (4)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole
Interior
The Gelda house, relax with a view

The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (14)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is AED 427
AED 606 total
includes taxes & fees
15 Dec - 16 Dec
The Gelda house, relax with a view
Pool
Eva's house awaits you!

Eva's house awaits you!

Eva's house awaits you!
Monterubiaglio
10.0 out of 10, Exceptional, (2)
"L'appartement est trÚs grand (rez-de-chaussée d'une maison) et aménagé avec bcp de goût. Tout etait fournis à l'arrivée : linges de lit, serviettes de toilette, liquide vaisselle, éponge et torchons. L'accueil des propriétaires etaient chaleureux et leurs conseils bienvenus. Chien, chat, tortues nous ont réservés un acceuil amical. Le jardin est trÚs grand, idéal lorsqu'on a des enfants. La piscine est un avantage non négligeable au vu des températures trÚs élevées. Les villages villes...
France
Stéphanie D.
The price is AED 491
AED 611 total
includes taxes & fees
11 Dec - 12 Dec
Eva's house awaits you!
Property grounds
Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is AED 299
AED 393 total
includes taxes & fees
11 Dec - 12 Dec
Holiday home with panoramic terrace ideal for families and couples
Property grounds
Romantic farm in the Sienese hills

Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den HĂŒgeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is AED 346
AED 747 total
includes taxes & fees
11 Dec - 12 Dec
Romantic farm in the Sienese hills
Exterior detail
Independent house in the historic center

Independent house in the historic center

Independent house in the historic center
CASTIGLIONE D'ORCIA
9.4 out of 10, Exceptional, (9)
"Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! "
United Kingdom
Graham S.
The price is AED 615
AED 730 total
includes taxes & fees
11 Dec - 12 Dec
Independent house in the historic center
Exterior
Le Roghete

Le Roghete

Le Roghete
Acquapendente
9.4 out of 10, Exceptional, (3)
"The address of the hotel was wrong on the Hotels.com web site. After an anxious hour or so our host was kind enough to come and get us, we were on foot walking the Via Francigena and the additional 4 miles back would have been a killer. Our host arranged for a cab the next morning so we were back on schedule. Worth the cab expense to keep on schedule. Wonderful evening meal and a great hotel. I would visit it again."
United States
Mark
Le Roghete
Fridge, stovetop, electric kettle, cookware/dishes/utensils
Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi

Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi

Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1)
"Pros: Es war ganz toll. Das Klima mit 34 Grad sehr heiß aber durch den Pool geht auch das sehr gut. Der Gastgeber ist super freundlich... wir sprechen null italienisch aber das war nur ein kleines Hinderniss."
Germany
Anonymous traveler
The price is AED 573
AED 590 total
includes taxes & fees
8 Jan - 9 January 2026
Apartment "PapĂ  Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Exterior detail
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is AED 683
AED 922 total
includes taxes & fees
15 Dec - 16 Dec
The House of Alice, charm and relaxation
Property grounds
Farmhouse in a medieval village between Umbria and Tuscany

Farmhouse in a medieval village between Umbria and Tuscany

Farmhouse in a medieval village between Umbria and Tuscany
Casaltondo
9.0 out of 10, Wonderful, (2)
"This apartment is located in a calm and charming little village, a good starting point to discover Umbria. The 3 bedrooms and 2 bathrooms make the place ideal for a family's comfortable stay. The apartment is well-equipped but we missed the air conditioning in the hot summer days and a microwave for easy cooking. The host were very nice and friendly. We can recommend this apartment for everyone who prefers a calm holiday."
United States
Edit K.
The price is AED 214
AED 461 total
includes taxes & fees
4 Jan - 5 January 2026
Farmhouse in a medieval village between Umbria and Tuscany
Dining
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Cortona
9.0 out of 10, Wonderful, (2)
"Pros: Il camino Ăš stato come tornare bambini.Atmosfera Natalizia e tanto di piĂč. Cons: Il BidĂš non funzionava."
Italy
Anonymous traveler
The price is AED 458
AED 475 total
includes taxes & fees
6 Jan - 7 January 2026
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Pool
Eagle House

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is AED 1,112
AED 1,509 total
includes taxes & fees
30 Dec - 31 Dec
Eagle House
Exterior
Montecchio di Cortona

Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AED 256
AED 333 total
includes taxes & fees
31 Dec - 1 January 2026
Montecchio di Cortona
Outdoor dining
Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is AED 512
AED 598 total
includes taxes & fees
12 Dec - 13 Dec
Podere Belsogno-camera Lavanda
Exterior detail
The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (17)
"The apartment is beautiful and the views are breathtaking! The local restaurant serves very authentic family style Tuscan cuisine and everyone was incredibly friendly and helpful. I wish we could have stayed longer!"
Australia
Andrew M.
The price is AED 683
AED 918 total
includes taxes & fees
16 Dec - 17 Dec
The Casetta di Brunello, quiet and breathtaking views
Outdoor dining
Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is AED 512
AED 692 total
includes taxes & fees
2 Jan - 3 January 2026
Il Borghetto - The House of Elba, rooftop panoramic terrace
1 bedroom, iron/ironing board, free WiFi, bed sheets
House in the Cortona countryside

House in the Cortona countryside

House in the Cortona countryside
Fratticciola
10.0 out of 10, Exceptional, (1)
"Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. "
United States
Nancy F.
The price is AED 384
AED 461 total
includes taxes & fees
11 Dec - 12 Dec
House in the Cortona countryside
Interior
"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8)
"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 AED 406
AED 500 total
includes taxes & fees
11 Dec - 12 Dec
"Il Focolare" Superior Apartment in Monticchiello
Dining
Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino
Montalcino
9.0 out of 10, Wonderful, (4)
"Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return."
United States
Larry V.
The price is AED 512
AED 598 total
includes taxes & fees
11 Dec - 12 Dec
Podere Belsogno-camera Rosmarino
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

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 3 days ago
Abbadia Sicille Relais

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