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Cheap Pienza Hotels

Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
$203 nightly
The price is $230 total per night
$230 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.13 mi from city center
When you stay at Hotel San Gregorio in Pienza, you'll be in the historical district and 16.4 mi (26.5 km) from Monte Oliveto Maggiore Abbey.
Pool
Pet friendly
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
$133 nightly
The price is $153 total per night
$153 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
0.19 mi from city center
Located in Pienza, Hotel Corsignano is in a regional park, a 4-minute walk from Pienza Cathedral and 6 minutes by foot from Piazza Pio II.
Hot Tub
Pet friendly
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26 Pienza SI
0.02 mi from city center
When you a stay at Hotel Relais II Chiostro di Pienza in Pienza, you'll be in the historical district, just steps from Chiesa di San Francesco and Palazzo Piccolomini.
Pool
Breakfast included
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
1.41 mi from city center
Located in Pienza, Agriturismo Il Macchione is in a rural location, within a 5-minute drive of Palazzo Piccolomini and Pienza Cathedral.
Pool
Breakfast included
Sant'Anna in Camprena Agriturismo

Sant'Anna in Camprena Agriturismo

Loc. Sant'Anna in Camprena Pienza SI
3.86 mi from city center
With a stay at Sant'Anna in Camprena Agriturismo in Pienza, you'll be in a regional park, just a 1-minute walk from Monastery of Sant'Anna in Camprena and 12 minutes by foot from Val di Chiana.
Breakfast included
Spa
Podere Spedalone

Podere Spedalone

1 out of 5
Strada per Cosona SP71 Pienza SI
3.91 mi from city center
Located in Pienza, Podere Spedalone is in the mountains, within a 15-minute drive of Monastery of Sant'Anna in Camprena and Palazzo Piccolomini.
Pool
Breakfast included
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
$257 nightly
The price is $292 total per night
$292 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.79 mi from city center
A stay at Monastero di Cortona Hotel & Spa places you in the heart of Cortona, within a 5-minute walk of Signorelli Theatre and Museum of the Etruscan Academy.
Pool
Hot Tub
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
$147 nightly
The price is $166 total per night
$166 total
Dec 22 - Dec 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
9.2 mi from city center
Located in Montepulciano, Relais Villa Grazianella - UNA Esperienze is in a rural location, within a 15-minute drive of Val di Chiana and Terme di Montepulciano Spa.
Pool
Parking included
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

4 out of 5
Via Umbria 2 Chianciano Terme SI
$87 nightly
The price is $100 total per night
$100 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
7.16 mi from city center
With a stay at Grand Hotel Admiral Palace in Chianciano Terme, you'll be within a 15-minute walk of Chianciano Art Museum and Piscine Termali Theia.
Pool
Hot Tub
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
$1,213 nightly
The price is $1,346 total per night
$1,346 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.99 mi from city center
With a stay at Castiglion del Bosco, A Rosewood Hotel in Montalcino, you'll be 7.8 mi (12.5 km) from Fortress of Montalcino and 11.7 mi (18.8 km) from Monte Oliveto Maggiore Abbey.
Pool
Spa
Fonteverde Lifestyle & Thermal Retreat

Fonteverde Lifestyle & Thermal Retreat

5 out of 5
Localita Terme, 1 San Casciano dei Bagni SI
$337 nightly
The price is $376 total per night
$376 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.87 mi from city center
With a stay at Fonteverde Lifestyle & Thermal Retreat in San Casciano dei Bagni, you'll be 0.1 mi (0.1 km) from Fonteverde Terme and 8.8 mi (14.1 km) from Monte Rufeno Nature Reserve.
Pool
Breakfast included
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
9.56 mi from city center
Located in Montalcino, Castello di Velona Resort Thermal SPA & Winery is in a national park, within a 15-minute drive of Abbazia di Sant'Antimo and Fortress of Montalcino.
Pool
Hot Tub
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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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Pienza hotels essential information

Accommodation
6,056 hotels
Lowest Price
$100
Highest Price
$1,346
Popular hotels
Hotel San Gregorio, Hotel Corsignano, Hotel Relais II Chiostro di Pienza, Agriturismo Il Macchione, Sant'Anna in Camprena Agriturismo, Podere Spedalone, Monastero di Cortona Hotel & Spa, Relais Villa Grazianella - UNA Esperienze, Grand Hotel Admiral Palace, Rosewood Castiglion del Bosco, Fonteverde Lifestyle & Thermal Retreat, Castello di Velona Resort Thermal SPA & Winery

Most Recent Pienza Hotel Reviews

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

5 out of 5
Posted 6 days ago
CheapTickets Verified Review
"Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!"
A verified traveler stayed at Relais Villa Grazianella - UNA Esperienze
Relais Villa Grazianella - UNA Esperienze