Pienza Holiday Rentals, Tuscany: Private House Rentals

A historic square with a prominent tower and statues.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Pienza

Pet friendly

Pool

Spa

Apartment

Apart hotel

Farm

Hot tub

Family friendly

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Pienza hotels

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

1. Relais Cloister Pienza

Pienza

Karen

3.319.487 ₫

3.825.306 ₫ total

includes taxes & fees

25 Oct - 26 Oct

Two people sitting at a round table outdoors with a scenic view of mountains in the background.

A breakfast buffet with various food items and beverages.

A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.

A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

2. Hotel Corsignano

Pienza

shane

3.010.866 ₫

3.485.824 ₫ total

includes taxes & fees

11 Nov - 12 Nov

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.

A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

3. Hotel San Gregorio

Pienza

Julia

3.345.857 ₫

3.854.430 ₫ total

includes taxes & fees

8 Nov - 9 Nov

An outdoor dining area with wooden tables and benches, stone walls, and greenery.

A modern living room with a white sofa, a coffee table, and a bookshelf.

A stone corridor with a vaulted ceiling and an arched doorway at the end.

A courtyard with a stone building, arched openings, and a covered seating area.

4. La Bandita Townhouse

Pienza

Kristian

11.854.812 ₫

13.156.236 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A villa with a swimming pool, terraced garden, and a view of distant mountains.

A stone building with a tiled roof, surrounded by a grassy area and flowering plants.

A fire pit with burning logs, surrounded by stone blocks and a metal grill.

A stone building with a gravel pathway leading to the entrance.

5. Agriturismo Il Macchione

Pienza

YOUNG BAE

3.399.257 ₫

3.855.096 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A modern interior with a stone wall, wooden paneling, and a television.

A rectangular swimming pool with clear water, surrounded by a brick patio.

A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.

A villa with a tower, a swimming pool, and a well-maintained garden.

6. Hotel Rutiliano Centro Benessere

Pienza

Marie

5.043.848 ₫

5.664.147 ₫ total

includes taxes & fees

15 Oct - 16 Oct

A patio area with outdoor seating, potted plants, and a view of the landscape.

A bedroom with a bed, a nightstand, a lamp, a chair, a table, and a window with a view of greenery.

A cozy living room with a fireplace, a dining area, and a black leather chair.

A well-maintained garden with a brick pathway, various potted plants, and trees.

7. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

2.809.597 ₫

3.812.121 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A narrow alleyway with stone walls and a brick floor, leading to a building with windows and balconies.

An aerial view of a historic building with a central tower, symmetrical roof design, and a decorative courtyard.

A hallway with an arched doorway leading to a bedroom with a bed and a dresser.

A couple on a balcony overlooking a historic town with terracotta roofs and a prominent clock tower.

8. Rossellino

Pienza

Darrell

2.615.237 ₫

3.572.245 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A cozy room with a fireplace, two armchairs, and a table.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

9. Tenuta Santo Pietro

Pienza

Robert

6.638.710 ₫

7.418.495 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

10. L'Olmo

Pienza

Michelle

11.591.398 ₫

12.866.452 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

A bedroom with a four-poster bed, a wooden chest, a desk with a chair, and a window with blue curtains.

A cozy dining area with a table, chairs, a flower centerpiece, and a window with curtains.

A wooden door with a sign, a staircase with blue steps, and a metal handrail.

11. PienzaLettings Suites

Pienza

Pearlyn

2.090.161 ₫

2.415.091 ₫ total

includes taxes & fees

2 Nov - 3 Nov

An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.

A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.

A rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.

A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.

12. Podere Spedalone

Pienza

Ardeshir

3.975.439 ₫

4.488.897 ₫ total

includes taxes & fees

30 Oct - 31 Oct

A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

A wooden desk with two chairs, each with a white cushion. The desk has a drawer and a small decorative item on top.

A staircase with a handrail leading to a door with a blue handle.

A compact kitchen with wooden cabinets, a microwave, and a sink.

13. TuscanyLettings Studio&Room

Pienza

Lucas

2.276.058 ₫

2.619.578 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A rustic stone building with a stone wall and a wooden fence.

A dining area with a wooden table, white pitcher, and bowl of fruit. There is a sofa and a window with curtains.

A bell with birds on a metal structure, a sunset in the background, and a grassy yard with chairs.

A cozy living room with a white sofa, a black bookshelf, and a stone wall.

14. Vento Dorcia

Pienza

Brendon

4.452.151 ₫

5.013.280 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A large, single-story building with a tiled roof, a covered patio area with outdoor seating, and a well-maintained lawn.

A bedroom with a four-poster bed, a wooden cabinet, and a window with lace curtains.

A two-story building with a flat roof and a small balcony on the second floor.

A breakfast buffet with various dishes and a person serving.

15. Agriturismo Poggio Tobruk

Pienza

Jennifer

A stone building with a wooden door, a staircase, and a small window with a metal grill.

A narrow street with buildings on either side, featuring balconies and potted plants.

A bedroom with a large bed, two bedside tables, a wooden wardrobe, and two wall-mounted lights.

16. Casa Gioia - Casa Olivieri

Pienza

Nancy

2.534.090 ₫

2.903.413 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A stone house with a tiled roof, a patio with a lounge chair, and a view of rolling hills in the background.

A serene outdoor pool area with a view of rolling hills and a sunset sky.

A spacious underground hall with brick arches, stone flooring, and a staircase leading to another level.

17. Relais Val d'Orcia

Pienza

Brittanie

6.213.832 ₫

6.951.129 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A couple in a hot spring with a large rock formation in the background.

A room with large windows offering a view of a garden with a yoga mat and a white cushion on the floor.

A restaurant with a bar area, dining tables, and chairs, with a view of the outdoors.

A hotel with a large building, a pool, and a landscaped garden.

18. ADLER Thermae

San Quirico d'Orcia

Abdel

18.974.380 ₫

21.016.710 ₫ total

includes taxes & fees

11 Nov - 12 Nov

A cave-like interior with a central hot spring, rocky formations, and a staircase leading to a higher level.

An indoor rock formation with a hot tub and a waterfall feature.

A cozy indoor seating area with a view of a swimming pool.

A rustic stone house with ivy-covered walls, a gravel driveway, and outdoor lighting.

19. Wellness Center Casanova Hotel e SPA

San Quirico d'Orcia

"It’s great for a 2-3 day stay ! Quiet , Cute and Tuscan style hotel . Between your Venice, Florence or Rome trip if you can squeeze in 2-3 days that will be more than enough to let you recharge. My father was able to get a massage and mentioned it was amazing , looks like those fill up quick , so if you are planning on getting massage make sure you book early. For sure go to the outdoor pool and indoor pool area . Cheers !"

ADRIAN

5.314.076 ₫

5.961.456 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A clear pool with a stone wall and a wooden bridge.

A narrow cobblestone street with a restaurant named "Trattoria al Vecchio Forno" and a sign indicating "Giardino" (garden).

An outdoor restaurant with tables and chairs, covered by a wooden roof, and surrounded by greenery.

A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

20. Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

San Quirico d'Orcia

Edward

5.488.531 ₫

6.182.277 ₫ total

includes taxes & fees

13 Oct - 14 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Pienza attractions

A historic church with a bell tower, arched windows, and a central dome.

Pienza Cathedral

9.4/10 (460 reviews)

Pope Pius II's Renaissance masterpiece showcases harmonious Gothic elements and luminous three-nave design. Arrive early to admire the 15th-century Sienese paintings and enjoy panoramic Tuscan views from the corridor.

See properties

Rolling green hills, a historic town with red-roofed buildings, and a prominent church tower.

Historic Centre of Pienza

9.6/10 (42 reviews)

Pienza's Historic Centre showcases Pope Pius II's Renaissance ideal city vision with harmonious architecture. Explore cobblestone streets, the Cathedral and Palazzo Piccolomini, and sample the town's famous pecorino cheese.

See properties

Palazzo Piccolomini

9.4/10 (199 reviews)

This Renaissance masterpiece was Pope Pius II's summer residence, designed by Bernardo Rossellino. From its hanging gardens, savour breathtaking panoramic views across the Val d'Orcia's rolling Tuscan landscape.

See properties

Piazza Pio II

9.2/10 (44 reviews)

This Renaissance masterpiece, designed by Bernardo Rossellino in 1459, showcases perfect architectural harmony at Pienza's heart. Explore the cathedral's artworks and enjoy sweeping Tuscan views from the elegant terrace.

See properties

Monastery of Sant'Anna in Camprena

This former monastery in the Tuscan hills showcases remarkable Renaissance frescoes in a tranquil setting. Savour authentic regional cuisine while staying overnight in the historic stone buildings.

See properties

Palazzo Vescovile

9.0/10 (12 reviews)

The Palazzo Vescovile showcases a captivating collection of religious art from the 14th-15th centuries. Admire Pietro Lorenzetti's Madonna di Monticchiello while exploring eleven rooms filled with sacred treasures.

See properties

Palazzo Borgia

8.8/10 (21 reviews)

This Renaissance palace houses the Museo Diocesano with masterpieces by Lorenzetti and Signorelli. Admire 12th-century crucifixes and medieval art while exploring the former residence of Cardinal Rodrigo Borgia.

See properties

Pieve di Corsignano

9.0/10 (17 reviews)

This 10th-century Romanesque church features a circular bell tower and Pope Pius II's baptismal font. Inside, soft light illuminates ancient stone carvings across its three-naved interior.

See properties

Learn more about Pienza

The Renaissance town's perfectly preserved architecture frames spectacular views of Val d'Orcia from its ancient walls. Sample Pecorino cheese at small shops along cobblestone streets or join locals for aperitivo in Piazza Pio II.

See all hotels in Pienza

A historic town perched on a hillside with a prominent church tower, surrounded by lush greenery and rolling hills in the background.

Top Pienza Hotel Reviews

Hotel San Gregorio

8/10 Good

"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Great, peaceful place to stay. Gorgeous property with pools and spa. Could use another food option but otherwise excellent."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Nice and quiet excellent hospitality"

Agriturismo Il Macchione

8/10 Good

"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"

Nuovo Etruria Resort

10/10 Excellent

"Beautiful pool with view. Friendly staff members. Town is walkable but there is also a bus stop nearby that does the uphill drive to the top of town. Maybe not the most suitable for those who have proper mobility concerns for getting into town, but for everyone else the location is great"

Palazzuolo

10/10 Excellent

"Excellent room, good location, the staff is very gentle, the breakfast is good"

Hotel Certosa Di Maggiano

10/10 Excellent

"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"

Hotel Villa Ricci

10/10 Excellent

"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."

More cheap stays in Pienza

Albergo Le Macinaie

Loc. Prato Le Macinaie Castel del Piano GR

1.080.028 ₫

1.246.075 ₫ total

13 Oct - 14 Oct

includes taxes & fees

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

1.997.303 ₫

2.283.969 ₫ total

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (50 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

2.897.849 ₫

3.303.548 ₫ total

14 Oct - 15 Oct

includes taxes & fees

9.4/10 Exceptional! (214 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI

Get rates

8.6/10 Excellent! (44 reviews)

Amiata Suite

Via Trieste 10 Abbadia San Salvatore SI

Get rates

Hotels in Pienza with star rating

Frequently asked questions

What's the weather like in Pienza?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Pienza is 1065 mm.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Pienza on Expedia.it

Find hotels in Pienza from 1.246.075 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Pienza

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pienza hotels

1. Relais Cloister Pienza

2. Hotel Corsignano

3. Hotel San Gregorio

4. La Bandita Townhouse

5. Agriturismo Il Macchione

6. Hotel Rutiliano Centro Benessere

7. Affitacamere Maria Gabriella

8. Rossellino

9. Tenuta Santo Pietro

10. L'Olmo

11. PienzaLettings Suites

12. Podere Spedalone

13. TuscanyLettings Studio&Room

14. Vento Dorcia

15. Agriturismo Poggio Tobruk

16. Casa Gioia - Casa Olivieri

17. Relais Val d'Orcia

18. ADLER Thermae

19. Wellness Center Casanova Hotel e SPA

20. Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

Stay near popular Pienza attractions

Pienza Cathedral

Historic Centre of Pienza

Palazzo Piccolomini

Piazza Pio II

Monastery of Sant'Anna in Camprena

Palazzo Vescovile

Palazzo Borgia

Pieve di Corsignano

Learn more about Pienza

Top Pienza Hotel Reviews

Hotel San Gregorio

Precise Tale Poggio Alla Sala

Castiglion del Bosco, A Rosewood Hotel

Agriturismo Il Macchione

Nuovo Etruria Resort

Palazzuolo

Hotel Certosa Di Maggiano

Hotel Villa Ricci

Castello di Velona Resort Thermal SPA & Winery

More cheap stays in Pienza

Albergo Le Macinaie

Torre del Fuggisole

Hotel La Terrazza di Montepulciano

Porta Pispini Residence

La Locanda di Casalmustia

Amiata Suite

Hotels in Pienza with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app