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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montepulciano vacation 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 ￥19,136
￥28,704 total
includes taxes & fees
Oct 20 - Oct 21
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 traveler
The price is ￥25,692
￥35,260 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Home in Villa Pandolfina near Montepulciano
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

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 ￥17,719
￥21,617 total
includes taxes & fees
Nov 5 - Nov 6
"Il Focolare" Superior Apartment in Monticchiello
An aerial view of a rural property with vineyards, olive groves, and a red-roofed building with a swimming pool.

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 ￥31,734
￥45,909 total
includes taxes & fees
Oct 13 - Oct 14
Eagle House
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

5. 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 ￥32,213
￥42,719 total
includes taxes & fees
Oct 12 - Oct 13
Suite Gioconda - Podere Casa Rossa in Pienza
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

6. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
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.

7. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is ￥26,578
￥60,421 total
includes taxes & fees
Oct 10 - Oct 11
Agritourism in val d'orcia
An outdoor patio with a table and chairs, a view of the countryside, and a stone wall.

8. 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 ￥118,645
￥119,354 total
includes taxes & fees
Oct 9 - Oct 10
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.

9. 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 ￥13,681
￥14,393 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
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 ￥19,136
￥36,500 total
includes taxes & fees
Oct 10 - Oct 11
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, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano

Apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is ￥43,310
￥43,844 total
includes taxes & fees
Nov 4 - Nov 5
Apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano
A narrow stone alley with potted plants and benches.

12. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (77 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is ￥26,578
￥36,146 total
includes taxes & fees
Nov 5 - Nov 6
The House of Alice, charm and relaxation
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

13. 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
The price is ￥17,542
￥24,984 total
includes taxes & fees
Oct 20 - Oct 21
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A stone building with a sign reading "Borgo di Mezzo".

14. The Gelda house, relax with a view

The Gelda house, 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 ￥17,719
￥25,161 total
includes taxes & fees
Oct 20 - Oct 21
The Gelda house, relax with a view
A stone building with a wooden door and two windows with shutters.

15. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is ￥26,578
￥36,146 total
includes taxes & fees
Nov 3 - Nov 4
The Casetta di Brunello, quiet and breathtaking views
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,218
￥14,423 total
includes taxes & fees
Oct 8 - Oct 9
Holiday home with panoramic terrace ideal for families and couples
A terrace with a table set for breakfast, overlooking a mountainous landscape.

17. Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is ￥21,263
￥29,060 total
includes taxes & fees
Oct 19 - Oct 20
Il Borghetto - The House of Elba, rooftop panoramic terrace
A stone building with a tiled roof, a staircase leading to a lower level, and a garden with various plants.

18. Double bedroom with private bathroom, private access, garden and swimming pool

Double bedroom with private bathroom, private access, garden and swimming pool
Radicofani
The price is ￥14,175
￥14,884 total
includes taxes & fees
Nov 5 - Nov 6
Double bedroom with private bathroom, private access, garden and swimming pool
A kitchen with a tiled backsplash and three hanging utensils.

19. 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.
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
A building with a stone facade, multiple windows, and a balcony.

20. 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 ￥59,122
￥66,491 total
includes taxes & fees
Oct 11 - Oct 12
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
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

Terra Antica Resort

Terra Antica Resort

10/10 Excellent
"The property was perfect being set in the hills near Montepulchiano. The villa was excellent, clean, modernized yet still in the Italian style, and the amenities were great as well. A well rounded breakfast provided by staff, with exercise facilities for those of us who want to maintain workouts while on vacation. You can't go wrong staying here as your center for traveling to other villages in the area."
Kurt W 3-night trip
Posted 2 days ago
Terra Antica Resort

Find out more about Montepulciano

Montepulciano Vacation Homes information

Number of reviews
123
Accommodation
41 Vacation Homes
Lowest Price
￥14,393
Highest Price
￥119,354