Holiday Rentals in Pienza

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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, (171 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is €141
includes taxes & fees
16 Nov - 17 Nov
Hotel San Gregorio
A patio area with outdoor seating, potted plants, and a view of the landscape.

2. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (75 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is €132
includes taxes & fees
26 Nov - 27 Nov
Affitacamere Maria Gabriella
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

3. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (7 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is €88
includes taxes & fees
10 Dec - 11 Dec
PienzaLettings Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

4. 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 €90
includes taxes & fees
9 Dec - 10 Dec
TuscanyLettings Studio&Room
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 €85
includes taxes & fees
8 Dec - 9 Dec
Casa Gioia - Casa Olivieri
A poolside area with two glasses of water, candles, and a stone pathway.

6. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (105 reviews)
"Hotel had beautiful views and amenities like breakfast and spa were amazing."
United States
Oscar
The price is €180
includes taxes & fees
18 Nov - 19 Nov
Casanova - Panoramic Rooms and Suites
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 €95
includes taxes & fees
26 Nov - 27 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

8. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is €67
includes taxes & fees
26 Nov - 27 Nov
Abbadia Sicille Relais
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 €121
includes taxes & fees
15 Nov - 16 Nov
Sarna Residence
A stone building with a tiled roof, surrounded by tall trees and a gravel path.

10. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (12 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is €122
includes taxes & fees
13 Nov - 14 Nov
montorio
A terrace with a table set for breakfast, overlooking a scenic landscape.

11. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is €173
includes taxes & fees
13 Nov - 14 Nov
Delcorto Suites
An interior courtyard with stone columns, arches, and a mosaic.

12. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (122 reviews)
"The room was beautifully designed, clean and fresh with stunning views in a truly historic building. Family run and a special experience!!"
United States
Slimane
The price is €161
includes taxes & fees
13 Nov - 14 Nov
Meublé Il Riccio
A crowded restaurant with brick walls and multiple tables and chairs.

13. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 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 €147
includes taxes & fees
26 Nov - 27 Nov
La Locanda di San Francesco
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

14. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (141 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is €231
includes taxes & fees
13 Nov - 14 Nov
Il Tosco
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

15. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is €108
includes taxes & fees
30 Nov - 1 Dec
Bed & Breakfast Vicolo dell'Oste
An arched doorway leading to a building with a wooden door and a staircase.

16. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (117 reviews)
"Was a very nice spot"
Canada
Andrew
The price is €92
includes taxes & fees
18 Nov - 19 Nov
Residenza Fabroni
A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

17. Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful stay "
United States
Marc
The price is €345
includes taxes & fees
15 Nov - 16 Nov
Borgo Lucignanello Bandini
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

18. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is €98
includes taxes & fees
13 Dec - 14 Dec
Idolina Guest House
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

19. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"We had a great stay in this conveniently located property. The breakfast was good with many options and staff to assist."
Canada
Morris
The price is €121
includes taxes & fees
15 Nov - 16 Nov
B&B Le Scalette di Piazza
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

20. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is €263
includes taxes & fees
12 Dec - 13 Dec
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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Find holiday rentals that suit your style

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Top Pienza Hotel Reviews

A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.
Lupaia

Lupaia

Lupaia
Torrita di Siena

10/10 Excellent

We stayed at the hotel for 2 nights. The room was ,beautiful,spacious with very comfortable bed.Breakfast and dinner were delicious. We couldn't be happier!
Ireland
Anonymous traveller
Reviewed April 7, 2019
Lupaia

Find out more about Pienza

Everything you need to know about Pienza holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pienza holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pienza holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pienza. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza holiday rentals we have selected for you start as low as €66 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pienza rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pienza holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pienza. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

What are some of the best holiday rentals that Pienza has to offer?

House with private pool with beautiful view Val d 'Orcia: This highly rated holiday home rental in Pienza is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of books. Another good choice for your trip to Pienza is Villa I Cipressini Tuscany Private luxury pool spa.

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.