A hillside town with historic buildings and a prominent church.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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 AED 443
AED 631 total
includes taxes & fees
4 Nov - 5 Nov
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 AED 952
AED 1,173 total
includes taxes & fees
4 Nov - 5 Nov
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 AED 410
AED 471 total
includes taxes & fees
23 Nov - 24 Nov
"Il Focolare" Superior Apartment in Monticchiello
A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

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 AED 777
AED 1,061 total
includes taxes & fees
4 Nov - 5 Nov
Eagle House
A rustic brick building with a mural, a clock, and various potted plants.

5. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is AED 306
AED 398 total
includes taxes & fees
4 Nov - 5 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
An outdoor patio with a table and chairs, a view of the countryside, and a stone wall.

6. 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 AED 2,601
AED 2,617 total
includes taxes & fees
4 Nov - 5 Nov
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

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

Apartment with A/C, pool, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is AED 997
AED 1,009 total
includes taxes & fees
4 Nov - 5 Nov
Apartment with A/C, pool, WIFI, TV, terrace, pets allowed, panoramic view, close to Montepulciano
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

8. 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 AED 443
AED 803 total
includes taxes & fees
4 Nov - 5 Nov
Romantic farm in the Sienese hills
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 AED 316
AED 332 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A park with picnic tables, a playground, and a gravel path.

10. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is AED 259
AED 304 total
includes taxes & fees
4 Nov - 5 Nov
Vacation home with a panoramic terrace, ideal for families and couples
Dining

11. 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 AED 324
AED 369 total
includes taxes & fees
4 Nov - 5 Nov
Montecchio di Cortona
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

12. 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
10.0 out of 10, Exceptional, (1 review)
"Terme House is just as described. It had all of the amenities mentioned and was clean. We wanted a place just off ss2 - perfect location and quiet town. 5 stars!!!"
United States
Lori
The price is AED 407
AED 551 total
includes taxes & fees
6 Nov - 7 Nov
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A kitchen with wooden cabinets, a gas stove, a white dining table with chairs, and a view through a window.

13. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is AED 4,499
AED 4,499 total
includes taxes & fees
4 Nov - 5 Nov
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
A spacious living room with a wooden ceiling, a television, and large windows with curtains.

14. Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
Trequanda
The price is AED 1,918
AED 1,931 total
includes taxes & fees
4 Nov - 5 Nov
Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
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, (23 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is AED 615
AED 795 total
includes taxes & fees
18 Nov - 19 Nov
The Casetta di Brunello, quiet and breathtaking views
A pathway leading to a building with stone walls and a tree.

16. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is AED 440
AED 629 total
includes taxes & fees
5 Nov - 6 Nov
A typical Tuscan country house
A stone building with a sign reading "Borgo di Mezzo".

17. 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 AED 410
AED 553 total
includes taxes & fees
4 Nov - 5 Nov
The Gelda house, relax with a view
A patio area with a gravel floor, potted plants, and a white umbrella.

18. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 1,233
AED 1,538 total
includes taxes & fees
4 Dec - 5 Dec
Charming Siena Countryside Stay
A narrow stone alley with potted plants and benches.

19. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (79 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 615
AED 795 total
includes taxes & fees
27 Nov - 28 Nov
The House of Alice, charm and relaxation
A stone building with a dirt path leading to it, surrounded by greenery and trees.

20. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
The price is AED 2,897
AED 2,914 total
includes taxes & fees
5 Nov - 6 Nov
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
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

AgriHotel Villa Ambra

AgriHotel Villa Ambra

8/10 Good
"Staff was great, bee"
Janet 1-night trip
Posted 3 hours ago
AgriHotel Villa Ambra