A hillside town with historic buildings and a prominent church.

Search Holiday Homes in Montepulciano

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Montepulciano holiday homes

1 bedroom, iron/ironing board, WiFi, bed sheets

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 £141
includes taxes & fees
19 Aug - 20 Aug
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Outdoor dining

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 £295
includes taxes & fees
26 Aug - 27 Aug
Holiday Home in Villa Pandolfina near Montepulciano
Outdoor dining

3. 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 £224
includes taxes & fees
15 Sept - 16 Sept
Suite Gioconda - Podere Casa Rossa in Pienza
Property grounds

4. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is £109
includes taxes & fees
31 Aug - 1 Sept
A typical Tuscan country house
Front of property

5. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is £285
includes taxes & fees
20 Aug - 21 Aug
Zampugna
Exterior

6. 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 £245
includes taxes & fees
24 Aug - 25 Aug
Eagle House
Exterior

7. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is £268
includes taxes & fees
5 Sept - 6 Sept
Oasi del Borgo Montefollonico
Outdoor pool

8. Villa Pesca - Cignella Resort Val D'orcia Toscana

Villa Pesca - Cignella Resort Val D'orcia Toscana
Toscana
The price is £4,877
includes taxes & fees
6 Sept - 7 Sept
Villa Pesca - Cignella Resort Val D'orcia Toscana
Pool

9. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is £292
includes taxes & fees
19 Aug - 20 Aug
Agritourism in val d'orcia
Outdoor dining

10. 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 £404
additional charges may apply
20 Aug - 21 Aug
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Living area

11. Villino Basilico - Cignella Resort Toscana

Villino Basilico - Cignella Resort Toscana
Toscana
The price is £248
includes taxes & fees
27 Aug - 28 Aug
Villino Basilico - Cignella Resort Toscana
Outdoor dining

12. 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
19 Aug - 20 Aug
Holiday home with panoramic terrace ideal for families and couples
Interior

13. 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 £133
includes taxes & fees
1 Sept - 2 Sept
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Property grounds

14. 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 £178
includes taxes & fees
25 Aug - 26 Aug
Romantic farm in the Sienese hills
Property grounds

15. 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 £163
includes taxes & fees
19 Aug - 20 Aug
Holiday Home 'Colline' with Balcony and Wi-Fi
Exterior detail

16. 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 £74
includes taxes & fees
19 Aug - 20 Aug
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
2 bedrooms, iron/ironing board, free WiFi, bed sheets

17. Terme house

Terme house
Bagni San Filippo
The price is £124
includes taxes & fees
22 Aug - 23 Aug
Terme house
Property grounds

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 £106
includes taxes & fees
19 Aug - 20 Aug
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Dining

19. 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
24 Aug - 25 Aug
Montecchio di Cortona
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montepulciano Hotel Reviews

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Gorgeous tranquil property next to a winery. We did the winery tour and tasting and it was lovely. We rented e-bikes for the day and biked through the vineyards. We enjoyed the pool but had to go to the bar for service. Dinner outside was fantastic. Breakfast had a great variety. Room was spacious and clean. AC worked well. It’s a 20 minute drive to the town of Montepulciano."
Eric 2-night trip
Posted 2 hours ago
Relais Villa Grazianella - UNA Esperienze

Find out more about Montepulciano

Montepulciano Holiday Homes information

Number of reviews
5
Accommodation
34 Holiday Homes
Lowest Price
£285
Highest Price
£285