A hillside town with historic buildings and a prominent church.

Holiday Homes in Montepulciano

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Montepulciano holiday homes

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

1. 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 AU$258
includes taxes & fees
6 Nov - 7 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

2. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is AU$294
includes taxes & fees
2 Nov - 3 Nov
Holiday Home in Villa Pandolfina near Montepulciano
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

3. "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 AU$197
includes taxes & fees
29 Oct - 30 Oct
"Il Focolare" Superior Apartment in Monticchiello
A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

4. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"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 AU$421
includes taxes & fees
6 Nov - 7 Nov
Eagle House
A rustic brick building with a mural, a clock, and various potted plants.

5. 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 AU$149
includes taxes & fees
22 Nov - 23 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A stone building with a dirt path leading to it, surrounded by greenery and trees.

6. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
The price is AU$1,504
includes taxes & fees
2 Nov - 3 Nov
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
A trampoline with a safety net enclosure, set up on a grassy lawn.

7. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
The price is AU$528
includes taxes & fees
31 Oct - 1 Nov
Agritourism in Val d'Orcia
A brick building with a large sliding glass door, a brown door, and a small potted plant.

8. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is AU$129
includes taxes & fees
4 Nov - 5 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

9. 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 AU$320
includes taxes & fees
29 Oct - 30 Oct
Romantic farm in the Sienese hills
A park with picnic tables, a playground, and a gravel path.

10. 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 AU$132
includes taxes & fees
28 Oct - 29 Oct
Vacation home with a panoramic terrace, ideal for families and couples
A stone building with a sign reading "Borgo di Mezzo".

11. 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 AU$229
includes taxes & fees
6 Nov - 7 Nov
The Gelda house, relax with a view
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

12. 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 AU$227
includes taxes & fees
29 Oct - 30 Oct
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A narrow stone alley with potted plants and benches.

13. 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 AU$325
includes taxes & fees
1 Nov - 2 Nov
The House of Alice, charm and relaxation
A pathway leading to a building with stone walls and a tree.

14. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is AU$239
includes taxes & fees
23 Nov - 24 Nov
A typical Tuscan country house
A patio area with a gravel floor, potted plants, and a white umbrella.

15. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AU$562
includes taxes & fees
30 Oct - 31 Oct
Charming Siena Countryside Stay
A wooden staircase leading up a grassy hill, surrounded by a stone wall and a wooden fence.

16. Holiday Home 'Colline' with Balcony and Wi-Fi

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
8.0 out of 10, Very good, (1 review)
The price is AU$305
includes taxes & fees
28 Oct - 29 Oct
Holiday Home 'Colline' with Balcony and Wi-Fi
A stone building with a wooden door and two windows with shutters.

17. 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 AU$326
includes taxes & fees
3 Nov - 4 Nov
The Casetta di Brunello, quiet and breathtaking views
Dining

18. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AU$157
includes taxes & fees
2 Nov - 3 Nov
Montecchio di Cortona
A terrace with a table set for breakfast, overlooking a mountainous landscape.

19. 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 AU$263
includes taxes & fees
31 Oct - 1 Nov
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
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 Montepulciano Hotel Reviews

Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Beautiful and perfect stay in Montepulciano!"
Krista 1-night trip
Posted less than an hour ago
Nuovo Etruria Resort

Find out more about Montepulciano

Montepulciano Holiday Homes information

Number of reviews
46
Accommodation
40 Holiday Homes
Lowest Price
AU$129
Highest Price
AU$1,504

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