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$976
HK$1,455 total
includes taxes & fees
3 Aug - 4 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$2,717
HK$2,934 total
includes taxes & fees
3 Aug - 4 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 HK$1,774
HK$2,289 total
includes taxes & fees
3 Aug - 4 Aug
Suite Gioconda - Podere Casa Rossa in Pienza
Front of property

4. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is HK$2,471
HK$2,745 total
includes taxes & fees
4 Aug - 5 Aug
Zampugna
Exterior

5. 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$1,989
HK$2,784 total
includes taxes & fees
31 Aug - 1 Sept
Eagle House
Outdoor dining

6. 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$633
HK$796 total
includes taxes & fees
8 Aug - 9 Aug
Holiday home with panoramic terrace ideal for families and couples
Property grounds

7. 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$976
HK$1,817 total
includes taxes & fees
6 Aug - 7 Aug
Romantic farm in the Sienese hills
Exterior detail

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 HK$744
HK$780 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Living area

9. Villino Basilico - Cignella Resort Toscana

Villino Basilico - Cignella Resort Toscana
Toscana
Villino Basilico - Cignella Resort Toscana
Interior

10. 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$994
HK$1,410 total
includes taxes & fees
1 Sept - 2 Sept
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Exterior

11. Villa Banditello, Secluded, Panoramic Views of Montepulciano Valley

Villa Banditello, Secluded, Panoramic Views of Montepulciano Valley
Torrita di Siena
Villa Banditello, Secluded, Panoramic Views of Montepulciano Valley
Dining

12. 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$714
HK$922 total
includes taxes & fees
19 Aug - 20 Aug
Montecchio di Cortona
Outdoor pool

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

Villa Pesca - Cignella Resort Val D'orcia Toscana
Toscana
The price is HK$45,200
HK$50,579 total
includes taxes & fees
3 Aug - 4 Aug
Villa Pesca - Cignella Resort Val D'orcia Toscana
Pool

14. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is HK$1,356
HK$3,092 total
includes taxes & fees
6 Aug - 7 Aug
Agritourism in val d'orcia
Exterior

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

Federico's Cantuccio, cozy apartment in the heart of Radicofani
Radicofani
The price is HK$578
HK$777 total
includes taxes & fees
31 Aug - 1 Sept
Federico's Cantuccio, cozy apartment in the heart of Radicofani
Property grounds

16. 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$895
HK$1,094 total
includes taxes & fees
8 Aug - 9 Aug
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Property grounds

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

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
The price is HK$1,505
HK$1,541 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Home 'Colline' with Balcony and Wi-Fi
Exterior

18. 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$1,056
HK$1,083 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
2 bedrooms, iron/ironing board, free WiFi, bed sheets

19. Terme house

Terme house
Bagni San Filippo
The price is HK$895
HK$1,275 total
includes taxes & fees
31 Aug - 1 Sept
Terme house
Private kitchen

20. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is HK$452
HK$651 total
includes taxes & fees
1 Sept - 2 Sept
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 3 days ago
Il Tosco

Find out more about Montepulciano

Montepulciano Vacation Homes information

Number of reviews
18
Accommodation
35 Vacation Homes
Lowest Price
HK$651
Highest Price
HK$50,579

Explore a world of travel with Expedia