A hillside town with historic buildings and a prominent church.

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Check prices for these dates

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

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 £140
includes taxes & fees
3 Oct - 4 Oct
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 £170
includes taxes & fees
2 Nov - 3 Nov
Holiday Home in Villa Pandolfina near Montepulciano
An aerial view of a rural property with vineyards, olive groves, and a red-roofed building with a swimming pool.

3. 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 £227
includes taxes & fees
13 Oct - 14 Oct
Eagle House
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

4. 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 £209
includes taxes & fees
5 Oct - 6 Oct
Suite Gioconda - Podere Casa Rossa in Pienza
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

5. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is £240
includes taxes & fees
4 Oct - 5 Oct
Oasi del Borgo Montefollonico
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

6. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is £299
includes taxes & fees
4 Oct - 5 Oct
Agritourism in val d'orcia
An outdoor patio with a table and chairs, a view of the countryside, and a stone wall.

7. 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 £574
includes taxes & fees
5 Oct - 6 Oct
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
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 £69
includes taxes & fees
5 Oct - 6 Oct
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A park with picnic tables, a playground, and a gravel path.

9. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is £72
includes taxes & fees
5 Oct - 6 Oct
Holiday home with panoramic terrace ideal for families and couples
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

10. 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 £179
includes taxes & fees
5 Oct - 6 Oct
Romantic farm in the Sienese hills
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

11. Apartment with pool, A/C, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano

Apartment with pool, A/C, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is £210
includes taxes & fees
6 Oct - 7 Oct
Apartment with pool, A/C, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano
A pathway leading to a building with stone walls and a tree.

12. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is £128
includes taxes & fees
5 Oct - 6 Oct
A typical Tuscan country house
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

13. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is £91
includes taxes & fees
4 Oct - 5 Oct
Dolce Casa 2 by Tiny Away
A kitchen with a tiled backsplash and three hanging utensils.

14. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Castiglione del Lago
10.0 out of 10, Exceptional, (1 review)
"Great location in beautiful Tuscany. Very nice host and hospitallity. Would come back again!"
United States
Bin L.
The price is £148
includes taxes & fees
4 Oct - 5 Oct
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Dining

15. 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 £86
includes taxes & fees
19 Oct - 20 Oct
Montecchio di Cortona
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 £123
includes taxes & fees
14 Oct - 15 Oct
Terme house
A building with a stone facade, multiple windows, and a balcony.

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 £351
includes taxes & fees
14 Oct - 15 Oct
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A narrow stone staircase leading to a building with balconies adorned with flower pots.

18. La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia

La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Radicofani
The price is £122
includes taxes & fees
5 Oct - 6 Oct
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
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

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Beautiful property in the middle of a vineyard! Relaxing."
Kimberly 2-night trip
Posted 7 hours ago
Precise Tale Poggio Alla Sala

Find out more about Montepulciano

Montepulciano Holiday Homes information

Number of reviews
14
Accommodation
34 Holiday Homes
Lowest Price
£69
Highest Price
£574