A historic square with a prominent tower and statues.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pienza holiday rentals

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

1. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (161 reviews)
"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"
United States
Julia
The price is 3.345.857 ₫
3.854.430 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

2. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is 2.276.058 ₫
2.619.578 ₫ total
includes taxes & fees
2 Nov - 3 Nov
TuscanyLettings Studio&Room
A patio area with outdoor seating, potted plants, and a view of the landscape.

3. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is 2.809.597 ₫
3.812.121 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Affitacamere Maria Gabriella
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

4. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is 2.090.161 ₫
2.415.091 ₫ total
includes taxes & fees
2 Nov - 3 Nov
PienzaLettings Suites
A stone building with a wooden door, a staircase, and a small window with a metal grill.

5. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is 2.534.090 ₫
2.903.413 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Casa Gioia - Casa Olivieri
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

6. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is 11.591.398 ₫
12.866.452 ₫ total
includes taxes & fees
2 Nov - 3 Nov
L'Olmo
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

7. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is 3.175.753 ₫
3.609.271 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A poolside area with two glasses of water, candles, and a stone pathway.

8. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is 4.636.559 ₫
5.216.129 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Casanova - Panoramic Rooms and Suites
A stone building with a courtyard, outdoor seating, and a warm light setting.

9. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is 2.871.479 ₫
3.506.398 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Sarna Residence
A historic building with a tower, a courtyard, and a well-lit entrance.

10. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is 2.252.209 ₫
2.564.307 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Abbadia Sicille Relais
An arched doorway leading to a building with a wooden door and a staircase.

11. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (114 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is 1.896.086 ₫
2.201.609 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Residenza Fabroni
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

12. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is 2.726.732 ₫
3.115.319 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

13. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is 2.197.383 ₫
2.648.949 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Idolina Guest House
A crowded restaurant with brick walls and multiple tables and chairs.

14. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (150 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is 4.610.189 ₫
5.187.122 ₫ total
includes taxes & fees
3 Nov - 4 Nov
La Locanda di San Francesco
An interior courtyard with stone columns, arches, and a mosaic.

15. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is 4.129.435 ₫
4.658.293 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Meublé Il Riccio
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

16. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is 6.668.241 ₫
7.624.821 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Palazzo Saloni
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 San Gregorio

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"
Julia 2-night trip
Posted 3 days ago
Hotel San Gregorio

Frequently asked questions

Can I find a holiday rental in Pienza?

Yes, there are holiday rentals in Pienza close to Art Studio di Adelina Quadri, or you can select a more secluded option if you're looking for a relaxing stay. Pienza is known for its churches and wineries. Make sure you have time to check out the temples while you're in the area.

How many holiday rentals are there in Pienza?

Expedia has 30 holiday rentals for your stay in Pienza.

What’s there to see and do in Pienza?

Cultural attractions include Palazzo Borgia and Artemisia Gallery, whereas Historic Centre of Pienza and Val di Chiana are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Palazzo Piccolomini and Pienza Cathedral.

What’s a holiday rental in Pienza like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pienza. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.