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

Holiday Homes in Montalcino

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Check prices for these dates

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

Our top choices for Montalcino holiday 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 NZ$277
includes taxes & fees
2 Nov - 3 Nov
Podere Belsogno-camera Lavanda
A narrow stone alley with potted plants and benches.

2. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (78 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is NZ$394
includes taxes & fees
1 Nov - 2 Nov
The House of Alice, charm and relaxation
A stone building with a wooden door and two windows with shutters.

3. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (23 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is NZ$390
includes taxes & fees
3 Nov - 4 Nov
The Casetta di Brunello, quiet and breathtaking views
A stone building with a sign reading "Borgo di Mezzo".

4. 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 NZ$281
includes taxes & fees
26 Oct - 27 Oct
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.

5. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
The price is NZ$654
includes taxes & fees
21 Oct - 22 Oct
Agritourism in Val d'Orcia
A terrace with a table set for breakfast, overlooking a mountainous landscape.

6. 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 NZ$321
includes taxes & fees
31 Oct - 1 Nov
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
A narrow stone corridor with a vaulted ceiling, leading to a room with a long table and chairs.

7. 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 NZ$2,378
includes taxes & fees
21 Oct - 22 Oct
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
A pathway leading to a building with stone walls and a tree.

8. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is NZ$246
includes taxes & fees
13 Nov - 14 Nov
A typical Tuscan country house
A patio area with a gravel floor, potted plants, and a white umbrella.

9. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is NZ$693
includes taxes & fees
21 Oct - 22 Oct
Charming Siena Countryside Stay
An outdoor seating area with a stone wall, a wooden door, and a table with chairs.

10. 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 NZ$929
includes taxes & fees
26 Oct - 27 Oct
Podere Giardino Wine & Bed – Glicine Apartment: Country House with Pool, Wi-Fi & AC
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

11. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is NZ$279
includes taxes & fees
21 Oct - 22 Oct
Exclusive Stone Tower.
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

12. "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 NZ$242
includes taxes & fees
29 Oct - 30 Oct
"Il Focolare" Superior Apartment in Monticchiello
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

13. 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 NZ$455
includes taxes & fees
2 Nov - 3 Nov
Suite Gioconda - Podere Casa Rossa in Pienza
A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

14. Holday at Poggettone

Holday at Poggettone
Monteroni d'Arbia
The price is NZ$422
includes taxes & fees
29 Oct - 30 Oct
Holday at Poggettone
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

15. 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 NZ$234
includes taxes & fees
2 Nov - 3 Nov
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
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.

16. 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 NZ$507
includes taxes & fees
25 Oct - 26 Oct
Casa Crevole di Martina in the Heart of Tuscany
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 NZ$400
includes taxes & fees
21 Oct - 22 Oct
Romantic farm in the Sienese hills
A balcony with a tiled roof, a table with chairs, and a guitar leaning against the wall.

18. 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 NZ$503
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
A stone staircase with illuminated steps leading to a door with a glass panel.

19. Renovated Tuscan-style country house

Renovated Tuscan-style country house
Castel del Piano
The price is NZ$927
includes taxes & fees
2 Nov - 3 Nov
Renovated Tuscan-style country house
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

20. 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
The price is NZ$279
includes taxes & fees
2 Nov - 3 Nov
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
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
"Great location amazing place"
Rodolfo 1-night trip
Posted 3 hours ago
La Certosa di Pontignano

Find out more about Montalcino

Montalcino Holiday Homes information

Number of reviews
60
Accommodation
1292 Holiday Homes
Lowest Price
NZ$234
Highest Price
NZ$2,378