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Name: Castiglion del Bosco, A Rosewood Hotel
Price range: $1,359 total

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Cheap Pienza Hotels

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI

$127 nightly

$147 total

Nov 8 - Nov 9

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

Via Della Madonnina 11 Pienza SI

$130 nightly

$150 total

Nov 10 - Nov 11

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

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

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI

$146 nightly

$166 total

Nov 19 - Nov 20

Total with taxes and fees

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

Podere Spedalone

Strada per Cosona SP71 Pienza SI

$154 nightly

$174 total

Oct 30 - Oct 31

Total with taxes and fees

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

Tenuta Santo Pietro

Localita Santo Pietro 29 Pienza SI

$257 nightly

$288 total

Oct 22 - Oct 23

Total with taxes and fees

2.65 mi from city center

Located in Pienza, Tenuta Santo Pietro is a 1-minute drive from Val di Chiana and 6 minutes from Porta al Prato.

Pool

Breakfast included

Agriturismo Poggio Tobruk

Loc. Spedaletto Poggio Tobruk Pienza SI

2.42 mi from city center

With a stay at Agriturismo Poggio Tobruk in Pienza, you'll be 4.6 mi (7.4 km) from Piazza Pio II and 4.6 mi (7.5 km) from Pienza Cathedral.

Parking included

Free WiFi

Relais Val d'Orcia

S.P. 53 Km. 17,6 - Podere Tribbioli Pienza SI

$250 nightly

$280 total

Oct 27 - Oct 28

Total with taxes and fees

9.37 mi from city center

With a stay at Relais Val d'Orcia in Pienza, you'll be 10.4 mi (16.7 km) from Piscine Termali Theia and 12.2 mi (19.7 km) from Pieve di Corsignano.

Pool

Breakfast included

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

$629 nightly

$701 total

Oct 26 - Oct 27

Total with taxes and fees

21.72 mi from city center

When you stay at Villa di Piazzano - Small Luxury Hotel of the World in Cortona, you'll be in the historical district and 7.6 mi (12.2 km) from Lake Trasimeno.

Pool

Parking included

Precise Tale Poggio Alla Sala

Via Di Poggio Alla Sala, 10 Montepulciano SI

9.97 mi from city center

Located in Montepulciano, Precise Tale Poggio Alla Sala is in a rural location, a 1-minute drive from Val di Chiana and 7 minutes from Terme Sant'Elena.

Pool

Breakfast included

Nuovo Etruria Resort

Via di S. Martino snc Montepulciano SI

$117 nightly

$134 total

Oct 21 - Oct 22

Total with taxes and fees

Free Cancellation

6.2 mi from city center

With a stay at Nuovo Etruria Resort in Montepulciano, you'll be a 1-minute walk from Val di Chiana and 14 minutes by foot from Church of St. Agnes.

Pool

Free WiFi

Fonteverde Thermal Spa Resort Tuscany

Localita Terme, 1 San Casciano dei Bagni SI

$301 nightly

$335 total

Nov 2 - Nov 3

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

17.89 mi from city center

With a stay at Fonteverde Thermal Spa Resort Tuscany in San Casciano dei Bagni, you'll be 0.1 mi (0.1 km) from Fonteverde Terme and 8.7 mi (14.1 km) from Monte Rufeno Nature Reserve.

Pool

Breakfast included

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

$1,225 nightly

$1,359 total

Nov 3 - Nov 4

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

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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.

Pienza hotels essential information

Accommodation	5,986 hotels
Lowest Price	$134
Highest Price	$1,359
Popular hotels	Hotel San Gregorio, Hotel Corsignano, Agriturismo Il Macchione, Podere Spedalone, Tenuta Santo Pietro, Agriturismo Poggio Tobruk, Relais Val d'Orcia, Villa di Piazzano - Small Luxury Hotel of the World, Precise Tale Poggio Alla Sala, Nuovo Etruria Resort, Fonteverde Thermal Spa Resort Tuscany, Castiglion del Bosco, A Rosewood Hotel

Most Recent Pienza Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5

Posted 3 days ago

CheapTickets Verified Review

"This was an amazing stay recommended by a friend and we really loved this place. The only immediate issues were the A/C broke and the TV was hard to setup, and the toilet seat was cracked and broke when I sat on it. But they fixed all that on day 1 and we had an amazing time - staff was amazing, grounds, parking, quiet, romantic, everything. The restaurant was amazing wine cellar. The food a little exotic so if you want more basic - then head over to Cortona with a car 15 min drive up the hill. Best part of trip was having a car. The people amazing, Daniel, Enrico, and cant remember everyone - everyone was amazing."

A verified traveler stayed at Villa di Piazzano - Small Luxury Hotel of the World

Podere Spedalone

4 out of 5

Posted 7 days ago

CheapTickets Verified Review

"The shower drain was not adequate and bath room as well as into bedroom pooled with water. Had to use shower with very low flow. No coffee machine in the room, one machine in breakfast room which staff only operated starting at 8;00am. Definitely a minus as wanted coffee earlier, and like to still be in pajamas in room. Pillows were flat and not supportive of neck or head. One mile of very bumpy road leading to property. Lots of flies around due to chickens and sheep on property. Room would be quite warm in summer"

A verified traveler stayed at Podere Spedalone

Tenuta Santo Pietro

5 out of 5

Posted 8 days ago

CheapTickets Verified Review

"Tenuta Santo Pietro is truly a hidden gem, but what makes it so special is Bertina. She is, without a doubt, one of the most wonderful people I have ever encountered in all my years of traveling. Her warmth, kindness, attentiveness, and genuine love for what she does made our entire stay unforgettable. She goes above and beyond in every way and makes you feel so welcomed and cared for. I honestly cannot say enough wonderful things about her! The property is beautiful, the rooms are spacious, and the beds are incredibly comfortable. The restaurant is also absolutely incredible. After 10 days traveling throughout Italy, some of our favorite meals of the entire trip were here. From the exceptional wine to the pasta, desserts, and everything in between, every meal felt special. Tenuta Santo Pietro is a magical place, and Bertina is the heart of it. She made our stay truly unforgettable, and I cannot wait to return. I only hope she will be there to welcome us again. I have stayed in many wonderful places, but it is rare to meet someone who leaves such a lasting impression. Bertina is an absolute gem, and this property is so lucky to have her!"

A verified traveler stayed at Tenuta Santo Pietro

Agriturismo Il Macchione

4 out of 5

Posted 2 weeks ago

CheapTickets Verified Review

"We stayed at the olive Farmhouse across the street from the main property. Rooms were cozy and clean with some interesting toiletries to use (made from olive oil). The property also has a range of activities (extra) to choose from. Just a note that eventhough the farmhouse is close to the main property, you have to walk uphill to get to the property for breakfast or the pool. Also it is close to Pienza but on the north side (personally I think the south side is more picturesque). But overall, a good stay and property! Staff was very professional, friendly and always courteous"

A verified traveler stayed at Agriturismo Il Macchione

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Compare Cheap 3 Star Hotels

Secret Bargains - Save an extra 10% or more on select hotels

Check dates for Pienza hotels

Cheap Pienza Hotels

Hotel San Gregorio

Hotel Corsignano

Agriturismo Il Macchione

Podere Spedalone

Tenuta Santo Pietro

Agriturismo Poggio Tobruk

Relais Val d'Orcia

Villa di Piazzano - Small Luxury Hotel of the World

Precise Tale Poggio Alla Sala

Nuovo Etruria Resort

Fonteverde Thermal Spa Resort Tuscany

Castiglion del Bosco, A Rosewood Hotel

Pienza hotels essential information

Most Recent Pienza Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

Hotel San Gregorio

Podere Spedalone

Tenuta Santo Pietro

Fonteverde Thermal Spa Resort Tuscany

Agriturismo Il Macchione

More to Explore in Pienza

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