A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

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Our top choices for Montalcino vacation homes

1. Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"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 ¥21,126
¥22,358 total
includes taxes & fees
Nov 16 - Nov 17
Podere Belsogno-camera Lavanda

2. A Casetta di Brunello, tranquil and with breathtaking views.

A Casetta di Brunello, tranquil and with breathtaking views.
Montalcino
9.6 out of 10, Exceptional, (24 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is ¥26,407
¥32,745 total
includes taxes & fees
Nov 16 - Nov 17
A Casetta di Brunello, tranquil and with breathtaking views.

3. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
Castelnuovo dell'Abate
10.0 out of 10, Exceptional, (1 review)
"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...
Australia
Judith F.
The price is ¥21,126
¥26,231 total
includes taxes & fees
Nov 16 - Nov 17
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

4. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is ¥22,182
¥29,224 total
includes taxes & fees
Nov 22 - Nov 23
A typical Tuscan country house

5. Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"Super property! Will recommend to anyone. Fully operational properly, excellent location with so many restaurants around. We had a great time!"
United States
Shree S.
The price is ¥142,598
¥209,672 total
includes taxes & fees
Nov 16 - Nov 17
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

6. Podere Giardino Wine & Bed – Glicine Apartment: Country House with Pool, Wi-Fi & AC

Podere Giardino Wine & Bed – Glicine Apartment: Country House with Pool, Wi-Fi & AC
Montalcino
10.0 out of 10, Exceptional, (1 review)
"Podere Giardino is an amazing place to stay. You need a car but that’s true anywhere in Tuscany. Our apartment “Glicine” was 2 bedrooms and 2 bathrooms - a ton of space. It was clean and had absolutely everything you need to enjoy your stay. Super well stocked kitchen to cook a great meal. The pool was a highlight for us as it was hot outside and was very peaceful. We toured Italy for a month and this place was our favourite - truly a paradise away from the crowds. Ah the Tuscan...
Canada
Patrick D.
The price is ¥81,862
¥82,566 total
includes taxes & fees
Nov 30 - Dec 1
Podere Giardino Wine & Bed – Glicine Apartment: Country House with Pool, Wi-Fi & AC

7. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is ¥55,455
¥72,531 total
includes taxes & fees
Nov 16 - Nov 17
Charming Siena Countryside Stay

8. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is ¥14,101
¥23,431 total
includes taxes & fees
Nov 16 - Nov 17
Exclusive Stone Tower.

9. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
Monteroni d'Arbia
The price is ¥16,724
¥19,541 total
includes taxes & fees
Nov 24 - Nov 25
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

10. Vacation in Poggettone

Vacation in Poggettone
Monteroni d'Arbia
The price is ¥25,351
¥35,386 total
includes taxes & fees
Nov 22 - Nov 23
Vacation in Poggettone

11. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
Bagni San Filippo
10.0 out of 10, Exceptional, (1 review)
"Terme House is just as described. It had all of the amenities mentioned and was clean. We wanted a place just off ss2 - perfect location and quiet town. 5 stars!!!"
United States
Lori
The price is ¥17,429
¥23,590 total
includes taxes & fees
Nov 19 - Nov 20
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

12. Romantic farmhouse in the Sienese hills

Romantic farmhouse in the Sienese hills
Trequanda, Siena
7.0 out of 10, Good, (2 reviews)
"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...
United States
Harald B.
The price is ¥19,013
¥32,921 total
includes taxes & fees
Nov 16 - Nov 17
Romantic farmhouse in the Sienese hills

13. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
Poggiobrucoli
The price is ¥38,871
¥44,504 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

14. Renovated Tuscan-style country house

Renovated Tuscan-style country house
Castel del Piano
The price is ¥57,356
¥77,953 total
includes taxes & fees
Nov 16 - Nov 17
Renovated Tuscan-style country house

15. Double room with private bathroom in the countryside, 5 minutes from Montepulciano

Double room with private bathroom in the countryside, 5 minutes from Montepulciano
Toscana
The price is ¥19,013
¥27,111 total
includes taxes & fees
Nov 16 - Nov 17
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

16. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Detached house with a garden, just a few minutes from the Abbey of San Galgano
Toscana
10.0 out of 10, Exceptional, (1 review)
"Petite maison cosy et juste parfaite pour deux personnes. La localisation est très bonne, à l’entrée du village de Monticiano. L’accueil a été enthousiaste et la communication très fluide. Merci pour ce beau séjour ! On recommande !"
United States
Julie M.
The price is ¥8,802
¥20,069 total
includes taxes & fees
Nov 16 - Nov 17
Detached house with a garden, just a few minutes from the Abbey of San Galgano

17. A peaceful spot with a garden between Chianti and Crete, near the old town

A peaceful spot with a garden between Chianti and Crete, near the old town
Casetta
The price is ¥12,675
¥16,020 total
includes taxes & fees
Nov 16 - Nov 17
A peaceful spot with a garden between Chianti and Crete, near the old town

18. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is ¥12,962
¥16,899 total
includes taxes & fees
Dec 16 - Dec 17
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

19. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is ¥11,091
¥13,028 total
includes taxes & fees
Nov 16 - Nov 17
Vacation home with a panoramic terrace, ideal for families and couples

20. "Edera" Apartment in Agriturismo with Shared Pool, Mountain View, and Wi-Fi

"Edera" Apartment in Agriturismo with Shared Pool, Mountain View, and Wi-Fi
Arcidosso
10.0 out of 10, Exceptional, (1 review)
"Wir hatten einen E-Rollstuhl-Fahrer dabei. Die Unterkunft ist quasi perfekt dafür. Alles barrierefrei und gut rangierbar innerhalb der Wohnung. Nur der Eingang war etwas herausfordernd, aber machbar. Die eine Stufe wurde mit brettern überbrückt und war etwas wackelig. Insgesamt ist die Unterkunft sehr zu empfehlen. Mitten in der Natur und von Wald und wiesen umgeben, deshalb auch kühler. Wir hatten zu wenig warme Sachen dabei für Ende Mai!"
Germany
Ulrike R.
The price is ¥46,476
¥46,828 total
includes taxes & fees
Nov 16 - Nov 17
"Edera" Apartment in Agriturismo with Shared Pool, Mountain View, 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 Montalcino Hotel Reviews

Find out more about Montalcino

Montalcino Vacation Homes information

Number of reviews
47
Accommodation
1334 Vacation Homes
Lowest Price
¥13,028
Highest Price
¥209,672