A historic square with a prominent tower and statues.

Holiday Homes in Pienza

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Pienza holiday homes

A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

1. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
The price is €334
includes taxes & fees
31 Oct - 1 Nov
Agritourism in Val d'Orcia
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

2. 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
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A stone patio with a round table and chairs, surrounded by lush greenery and potted plants.

3. 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 €212
includes taxes & fees
31 Oct - 1 Nov
Romantic farm in the Sienese hills
A pathway leading to a building with stone walls and a tree.

4. A typical Tuscan country house

A typical Tuscan country house
Montalcino
A typical Tuscan country house
A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

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 €281
includes taxes & fees
31 Oct - 1 Nov
Eagle House
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

6. 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 €144
includes taxes & fees
2 Nov - 3 Nov
Podere Belsogno-camera Lavanda
A patio area with a gravel floor, potted plants, and a white umbrella.

7. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
Charming Siena Countryside Stay
A stone building with a wooden door and two windows with shutters.

8. 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 Casetta di Brunello, quiet and breathtaking views
A terrace with a table set for breakfast, overlooking a mountainous landscape.

9. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
Castelnuovo dell'Abate
10.0 out of 10, Exceptional, (1 review)
"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...
Australia
Judith F.
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

10. Cosy apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano

Cosy apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is €246
includes taxes & fees
31 Oct - 1 Nov
Cosy apartment with A/C, pool, WIFI, TV, patio, pets allowed, panoramic view, close to Montepulciano
A rustic brick building with a mural, a clock, and various potted plants.

11. 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 €97
includes taxes & fees
31 Oct - 1 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
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
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

13. 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 €286
includes taxes & fees
2 Nov - 3 Nov
Holiday Home in Villa Pandolfina near Montepulciano
A stone building with a stone wall and a small bridge, surrounded by trees and grass.

14. 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 €192
includes taxes & fees
31 Oct - 1 Nov
Holiday Home 'Colline' with Balcony and Wi-Fi
An outdoor patio with a table and chairs, a view of the countryside, and a stone wall.

15. 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 €639
includes taxes & fees
2 Nov - 3 Nov
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.

16. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
An open doorway leading to an outdoor area with a bench, a television on a cabinet, and a framed picture on the wall.

17. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
Monteroni d'Arbia
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
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 Pienza Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"One of the cleanest hotels I’ve ever seen. Very old but beautifully maintained. The bed was a little too hard. It was a lovely property and good value."
Rebecca 1-night trip
Posted 11 hours ago
Hotel Corsignano

Find out more about Pienza

Pienza Holiday Homes information

Number of reviews
37
Accommodation
1105 Holiday Homes
Lowest Price
€97
Highest Price
€639