Holiday Homes in Montepulciano

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Our top choices for Montepulciano holiday homes

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 NZ$305
includes taxes & fees
15 Nov - 16 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

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 NZ$549
includes taxes & fees
16 Nov - 17 Nov
Holiday Home in Villa Pandolfina near Montepulciano

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 NZ$229
includes taxes & fees
19 Nov - 20 Nov
"Il Focolare" Superior Apartment in Monticchiello

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 NZ$512
includes taxes & fees
17 Nov - 18 Nov
Eagle House

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 NZ$193
includes taxes & fees
15 Nov - 16 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

6. Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Torrita di Siena
The price is NZ$1,273
includes taxes & fees
15 Nov - 16 Nov
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

7. 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 NZ$161
includes taxes & fees
15 Nov - 16 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

8. 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 NZ$385
includes taxes & fees
15 Nov - 16 Nov
Romantic farmhouse in the Sienese hills

9. 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 NZ$147
includes taxes & fees
15 Nov - 16 Nov
Vacation home with a panoramic terrace, ideal for families and couples

10. 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 NZ$267
includes taxes & fees
17 Nov - 18 Nov
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

11. 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 NZ$179
includes taxes & fees
17 Nov - 18 Nov
Montecchio di Cortona

12. 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 NZ$381
includes taxes & fees
15 Nov - 16 Nov
A Casetta di Brunello, tranquil and with breathtaking views.

13. Alice's House, charm and relaxation

Alice's House, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (79 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is NZ$381
includes taxes & fees
15 Nov - 16 Nov
Alice's House, charm and relaxation

14. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is NZ$282
includes taxes & fees
23 Nov - 24 Nov
A typical Tuscan country house

15. Casa Gelda, relax with a view.

Casa Gelda, 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$269
includes taxes & fees
17 Nov - 18 Nov
Casa Gelda, relax with a view.

16. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is NZ$813
includes taxes & fees
15 Nov - 16 Nov
Charming Siena Countryside Stay

17. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is NZ$802
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

18. Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
Trequanda
The price is NZ$939
includes taxes & fees
16 Nov - 17 Nov
Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

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 NZ$309
includes taxes & fees
17 Nov - 18 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.

Learn more about Montepulciano

Renaissance palaces and medieval churches line the narrow streets of this hilltop town famous for Vino Nobile wine. Sample local wines at historic cellars beneath the Piazza Grande, then climb the tower at Palazzo Comunale for panoramic Tuscan countryside views.

A historic town with terracotta-roofed buildings, a prominent church, and rolling hills in the background.

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