A hillside town with historic buildings and a prominent church.

Search Vacation Homes in Montepulciano

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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 HK$972
HK$1,457 total
includes taxes & fees
31 Jul - 1 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
The price is HK$2,105
HK$2,321 total
includes taxes & fees
2 Aug - 3 Aug
Holiday Home in Villa Pandolfina near Montepulciano
Outdoor dining

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is HK$625
HK$786 total
includes taxes & fees
28 Aug - 29 Aug
Holiday home with panoramic terrace ideal for families and couples
Exterior

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 HK$1,979
HK$2,699 total
includes taxes & fees
23 Aug - 24 Aug
Eagle 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 HK$2,432
HK$2,702 total
includes taxes & fees
2 Aug - 3 Aug
Zampugna
Exterior detail

6. 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 HK$691
HK$727 total
includes taxes & fees
31 Jul - 1 Aug
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Interior

7. 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 HK$1,134
HK$1,547 total
includes taxes & fees
2 Aug - 3 Aug
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Property grounds

8. 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 HK$884
HK$1,080 total
includes taxes & fees
5 Aug - 6 Aug
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Pool

9. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is HK$1,339
HK$3,044 total
includes taxes & fees
7 Aug - 8 Aug
Agritourism in val d'orcia
2 bedrooms, iron/ironing board, free WiFi, bed sheets

10. Terme house

Terme house
Bagni San Filippo
The price is HK$891
HK$1,269 total
includes taxes & fees
16 Aug - 17 Aug
Terme house
Property grounds

11. 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 HK$964
HK$1,794 total
includes taxes & fees
6 Aug - 7 Aug
Romantic farm in the Sienese hills
Living area

12. Villino Basilico - Cignella Resort Toscana

Villino Basilico - Cignella Resort Toscana
Toscana
The price is HK$2,249
HK$2,564 total
includes taxes & fees
18 Aug - 19 Aug
Villino Basilico - Cignella Resort Toscana
Outdoor dining

13. 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 HK$4,660
HK$4,723 total
includes taxes & fees
16 Aug - 17 Aug
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Exterior

14. Federico's Cantuccio, cozy apartment in the heart of Radicofani

Federico's Cantuccio, cozy apartment in the heart of Radicofani
Radicofani
Federico's Cantuccio, cozy apartment in the heart of Radicofani
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 HK$711
HK$918 total
includes taxes & fees
19 Aug - 20 Aug
Montecchio di Cortona
Property grounds

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

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
The price is HK$1,498
HK$1,534 total
includes taxes & fees
2 Aug - 3 Aug
Holiday Home 'Colline' with Balcony and Wi-Fi
Exterior

17. Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is HK$1,051
HK$1,078 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Outdoor dining

18. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is HK$688
HK$956 total
includes taxes & fees
3 Aug - 4 Aug
Dolce Casa 2 by Tiny Away
Outdoor dining

19. 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 HK$1,080
HK$1,260 total
includes taxes & fees
31 Jul - 1 Aug
Podere Belsogno-camera Lavanda
Private kitchen

20. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is HK$729
HK$927 total
includes taxes & fees
31 Jul - 1 Aug
Happy Nest Tuscany Between Florence and Rome
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

Il Tosco

Il Tosco

10/10 Excellent
"By far best hotel I've stsyed in Ameneties were out of this world with the run of a 4000 sq ft apartment with 2 bedrooms, a ding room, full kitchen and a family room all tp our selves. Just minutes from shops and a fantastic view of the valley. The hostesses were awesome, informative and cooked us a special breakfast. What a great way to see Multapulciano, I must return soon with more family members soon!"
Mark 1-night trip
Posted 1 day ago
Il Tosco

Find out more about Montepulciano

Montepulciano Vacation Homes information

Number of reviews
18
Accommodation
35 Vacation Homes
Lowest Price
HK$727
Highest Price
HK$4,723

Explore a world of travel with Expedia