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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Montalcino vacation homes

An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

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 ￥21,480
￥25,060 total
includes taxes & fees
Oct 4 - Oct 5
Podere Belsogno-camera Lavanda
A stone building with a sign reading "Borgo di Mezzo".

2. The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (15 reviews)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is ￥17,900
￥25,418 total
includes taxes & fees
Oct 17 - Oct 18
The Gelda house, relax with a view
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

3. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is ￥26,850
￥60,501 total
includes taxes & fees
Sep 30 - Oct 1
Agritourism in val d'orcia
A terrace with a table set for breakfast, overlooking a mountainous landscape.

4. Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is ￥21,480
￥29,356 total
includes taxes & fees
Oct 6 - Oct 7
Il Borghetto - The House of Elba, rooftop panoramic terrace
A pathway leading to a building with stone walls and a tree.

5. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is ￥12,888
￥22,196 total
includes taxes & fees
Oct 2 - Oct 3
A typical Tuscan country house
A narrow stone corridor with a vaulted ceiling, leading to a room with a long table and chairs.

6. 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)
"Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa."
United States
Robert K.
The price is ￥161,097
￥224,104 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
An outdoor seating area with a stone wall, a wooden door, and a table with chairs.

7. 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 ￥83,234
￥83,950 total
includes taxes & fees
Oct 5 - Oct 6
Podere Giardino Wine & Bed – Glicine Apartment: Country House with Pool, Wi-Fi & AC
A patio area with a gravel floor, potted plants, and a white umbrella.

8. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is ￥48,329
￥60,859 total
includes taxes & fees
Oct 2 - Oct 3
Charming Siena Countryside Stay
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

9. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is ￥14,338
￥25,078 total
includes taxes & fees
Sep 30 - Oct 1
Exclusive Stone Tower.
Terrace/patio

10. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
Monteroni d'Arbia
The price is ￥17,184
￥21,301 total
includes taxes & fees
Oct 29 - Oct 30
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

11. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is ￥32,381
￥42,942 total
includes taxes & fees
Oct 5 - Oct 6
Suite Gioconda - Podere Casa Rossa in Pienza
A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

12. Holday at Poggettone

Holday at Poggettone
Monteroni d'Arbia
The price is ￥25,776
￥39,738 total
includes taxes & fees
Oct 5 - Oct 6
Holday at Poggettone
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

13. "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 ￥17,900
￥21,838 total
includes taxes & fees
Oct 5 - Oct 6
"Il Focolare" Superior Apartment in Monticchiello
Interior

14. Holiday Home 'Una Finestra Sulla Vetta' with Mountain View and Wi-Fi

Holiday Home 'Una Finestra Sulla Vetta' with Mountain View and Wi-Fi
Montelaterone
The price is ￥11,599
￥21,265 total
includes taxes & fees
Oct 5 - Oct 6
Holiday Home 'Una Finestra Sulla Vetta' with Mountain View and Wi-Fi
A rustic outdoor setting with a stone building, a wooden table with chairs, a brick oven, and a variety of greenery including tall cypress trees and flowering plants.

15. Casa Crevole di Martina in the Heart of Tuscany

Casa Crevole di Martina in the Heart of Tuscany
Murlo
10.0 out of 10, Exceptional, (1 review)
"Nach einer herzlichen Begrüßung durch die Gastgeberin haben wir ein paar entspannte Tage verbracht. Im Kühlschrank befanden sich für uns schon einmal keiner Erfrischungen. Obwohl wir nur 4 Nächte blieben, gab es einen Handtuchtausch nach 2 Tagen. Total überrascht hat uns aber der selbstgebackene Kuchen der für uns bereit stand. Wir würden hier jeder Zeit wieder Urlaub machen und können die Unterkunft mehr wir nur empehlen."
Germany
Sybille F.
The price is ￥41,257
￥45,625 total
includes taxes & fees
Oct 4 - Oct 5
Casa Crevole di Martina in the Heart of Tuscany
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

16. Terme house

Terme house
Bagni San Filippo
The price is ￥17,721
￥25,239 total
includes taxes & fees
Oct 1 - Oct 2
Terme house
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

17. Romantic farm in the Sienese hills

Romantic farm 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 ￥19,332
￥36,874 total
includes taxes & fees
Oct 5 - Oct 6
Romantic farm in the Sienese hills
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

18. Detached house with garden a few minutes from the abbey of San Galgano

Detached house with garden 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 ￥8,950
￥21,659 total
includes taxes & fees
Sep 30 - Oct 1
Detached house with garden a few minutes from the abbey of San Galgano
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

19. 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 ￥19,332
￥28,640 total
includes taxes & fees
Sep 30 - Oct 1
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A stone staircase with illuminated steps leading to a door with a glass panel.

20. Renovated Tuscan-style country house

Renovated Tuscan-style country house
Castel del Piano
The price is ￥70,238
￥96,730 total
includes taxes & fees
Oct 11 - Oct 12
Renovated Tuscan-style country house
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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"good to stay"
Jinhee 1-night trip
Posted 3 hours ago
La Certosa di Pontignano

Find out more about Montalcino

Montalcino Vacation Homes information

Number of reviews
37
Accommodation
1390 Vacation Homes
Lowest Price
￥21,659
Highest Price
￥224,104