A historic square with a prominent tower and statues.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pienza holiday homes

An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

1. 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 £209
includes taxes & fees
15 Sept - 16 Sept
Suite Gioconda - Podere Casa Rossa in Pienza
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

2. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is £301
includes taxes & fees
4 Sept - 5 Sept
Agritourism in val d'orcia
A stone building with a tiled roof, surrounded by dry grass and trees, set in a hilly landscape.

3. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is £400
includes taxes & fees
4 Sept - 5 Sept
Zampugna
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

4. 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 £141
includes taxes & fees
4 Sept - 5 Sept
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

5. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is £246
includes taxes & fees
5 Sept - 6 Sept
Oasi del Borgo Montefollonico
A pathway leading to a building with stone walls and a tree.

6. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is £109
includes taxes & fees
10 Sept - 11 Sept
A typical Tuscan country house
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

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 £180
includes taxes & fees
14 Sept - 15 Sept
Romantic farm in the Sienese hills
An aerial view of a rural property with vineyards, olive groves, and a red-roofed building with a swimming pool.

8. 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 £248
includes taxes & fees
4 Sept - 5 Sept
Eagle House
A stone building with a dirt path leading to it, surrounded by greenery and trees.

9. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
The price is £457
includes taxes & fees
7 Sept - 8 Sept
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

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

Cosy apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
Cosy apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano
A modern living room with a striped sofa, a white sofa, a fireplace, and a large window.

11. Villino Basilico - Cignella Resort Toscana

Villino Basilico - Cignella Resort Toscana
Toscana
The price is £250
includes taxes & fees
24 Sept - 25 Sept
Villino Basilico - Cignella Resort Toscana
A patio area with a gravel floor, potted plants, and a white umbrella.

12. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
Charming Siena Countryside Stay
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

13. 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 £123
includes taxes & fees
6 Sept - 7 Sept
Podere Belsogno-camera Lavanda
A street with outdoor seating, a building with a shop entrance, and a sign with a prohibition symbol.

14. 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 £114
includes taxes & fees
24 Sept - 25 Sept
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

15. Terme house

Terme house
Bagni San Filippo
The price is £124
includes taxes & fees
9 Sept - 10 Sept
Terme house

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

Villa Pesca - Cignella Resort Val D'orcia Toscana
Toscana
The price is £4,893
includes taxes & fees
6 Sept - 7 Sept
Villa Pesca - Cignella Resort Val D'orcia Toscana
A narrow stone staircase leading to a building with balconies adorned with flower pots.

17. 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 £107
includes taxes & fees
5 Sept - 6 Sept
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
A wooden staircase leading up a grassy hill, surrounded by a stone wall and a wooden fence.

18. 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 £171
includes taxes & fees
1 Oct - 2 Oct
Holiday Home 'Colline' with Balcony and 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.
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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Unique and beautifully appointed hotel. We loved our stay here. The spa is lovely and the food was fabulous. The staff are wonderful especially Allesandro, Federico, Orlando, Matteo and all the lovely staff at breakfast. The housekeeping staff were very friendly and we had an amazing time here. We stayed for 10 nights so got to know Cortona and the surrounding area very well."
Vanessa 10-night trip
Posted 15 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Pienza

Pienza Holiday Homes information

Number of reviews
20
Accommodation
1123 Holiday Homes
Lowest Price
£107
Highest Price
£4,893

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