A historic square with a prominent tower and statues.

Search Pienza Cottage Rentals from CA $116

  • 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

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31
No exact matches found, but these alternatives could be just right

Recommended hotels in Pienza

A historic town with a prominent church, a square with a pool, and a well-lit street.

1. Relais Cloister Pienza

Relais Cloister Pienza
4.0 star property
Pienza
9.6 out of 10, Exceptional, (7 reviews)
"Just a fantastic place in the most beautiful setting. Medieval historical ambiance with a modern vibe. Pool area - perfect. Breakfast - perfect. Dinner - perfect. Views - incredible! Location - the best in town!"
United States
Karen
The price is CA $183
CA $211 total
includes taxes & fees
Oct 25 - Oct 26
Relais Cloister Pienza
An outdoor patio with tables and chairs, surrounded by greenery and buildings in the background.

2. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (161 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is CA $184
CA $212 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
Two people sitting at a round table outdoors with a scenic view of mountains in the background.

3. Hotel Corsignano

Hotel Corsignano
4.0 star property
Pienza
9.4 out of 10, Exceptional, (387 reviews)
"Nice staff great location wonderful breakfast"
United States
shane
The price is CA $197
CA $227 total
includes taxes & fees
Nov 8 - Nov 9
Hotel Corsignano
A stone building with a gravel pathway leading to the entrance.

4. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
9.6 out of 10, Exceptional, (81 reviews)
"very kind and friendly staff. well managed facilities. I had a great stay and strongly recommand to be stay there."
South Korea
YOUNG BAE
The price is CA $193
CA $219 total
includes taxes & fees
Nov 5 - Nov 6
Agriturismo Il Macchione
A courtyard with a stone building, arched openings, and a covered seating area.

5. La Bandita Townhouse

La Bandita Townhouse
Pienza
9.4 out of 10, Exceptional, (16 reviews)
"Great Stay!"
United States
Kristian
The price is CA $505
CA $562 total
includes taxes & fees
Nov 7 - Nov 8
La Bandita Townhouse
A narrow alleyway with stone walls and a brick floor, leading to a building with windows and balconies.

6. Rossellino

Rossellino
Pienza
8.6 out of 10, Excellent, (70 reviews)
"Very nice people. Glad we stayed there. Would absolutely stay there again!"
United States
Darrell
The price is CA $135
CA $187 total
includes taxes & fees
Nov 1 - Nov 2
Rossellino
A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

7. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (134 reviews)
"Gorgeous location with spectacular views and yummy food with very friendly and helpful staff"
United States
Robert
The price is CA $286
CA $321 total
includes taxes & fees
Nov 7 - Nov 8
Tenuta Santo Pietro
A villa with a tower, a swimming pool, and a well-maintained garden.

8. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
3.0 star property
Pienza
8.8 out of 10, Excellent, (12 reviews)
"Host was wonderful Location was great"
United States
Marie
The price is CA $278
CA $312 total
includes taxes & fees
Oct 10 - Oct 11
Hotel Rutiliano Centro Benessere
A patio area with outdoor seating, potted plants, and a view of the landscape.

9. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (70 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is CA $144
CA $199 total
includes taxes & fees
Oct 14 - Oct 15
Affitacamere Maria Gabriella
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

10. 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 CA $115
CA $133 total
includes taxes & fees
Nov 2 - Nov 3
PienzaLettings Suites
An outdoor patio with stone walls, tables, and chairs, overlooking a field.

11. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is CA $639
CA $709 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

12. 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 CA $110
CA $128 total
includes taxes & fees
Nov 4 - Nov 5
TuscanyLettings Studio&Room
A stone building with a cobblestone courtyard, potted plants, and a street lamp.

13. Podere Spedalone

Podere Spedalone
1.0 star property
Pienza
9.4 out of 10, Exceptional, (50 reviews)
"Ask for dinner menu before you opt for having dinner to make sure you like it"
United States
Ardeshir
The price is CA $219
CA $247 total
includes taxes & fees
Oct 30 - Oct 31
Podere Spedalone
A traditional stone building with multiple windows and doors, a courtyard with a table and chairs, and a clear blue sky with clouds.

14. 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 CA $134
CA $154 total
includes taxes & fees
Nov 5 - Nov 6
Casa Gioia - Casa Olivieri
A stone house with a tiled roof, a patio with a lounge chair, and a view of rolling hills in the background.

15. Relais Val d'Orcia

Relais Val d'Orcia
Pienza
10.0 out of 10, Exceptional, (58 reviews)
"Fantastic stay "
United States
Brittanie
The price is CA $342
CA $383 total
includes taxes & fees
Oct 25 - Oct 26
Relais Val d'Orcia
A stone building with a courtyard and a canal.

16. Palazzo Brandano

Palazzo Brandano
Trequanda
9.4 out of 10, Exceptional, (103 reviews)
"Lovely hotel in centre of village, room was very spacious and clean. Reception staff very welcoming on arrival and helpful. Free parking was available in nearby public car park."
United Kingdom
Andrew
The price is CA $101
CA $116 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo Brandano
An aerial view of a town with a central square, a swimming pool, and surrounding residential buildings.

17. Palazzuolo

Palazzuolo
3.0 star property
San Quirico d'Orcia
8.2 out of 10, Very good, (203 reviews)
"Very clean! helpful staff!. Nice location."
United States
Alberto
The price is CA $142
CA $162 total
includes taxes & fees
Oct 25 - Oct 26
Palazzuolo
A rustic stone house with ivy-covered walls, a gravel driveway, and outdoor lighting.

18. Wellness Center Casanova Hotel e SPA

Wellness Center Casanova Hotel e SPA
3.0 star property
San Quirico d'Orcia
8.4 out of 10, Very good, (148 reviews)
"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 !"
United States
ADRIAN
The price is CA $293
CA $328 total
includes taxes & fees
Oct 12 - Oct 13
Wellness Center Casanova Hotel e SPA
A covered outdoor seating area with white wicker furniture and potted plants.

19. Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.4 out of 10, Exceptional, (182 reviews)
"Beautiful and sparkling clean property. Excellent location in walking distance from lovely shops and restaurants. Wonderful staff and the best breakfast of all the properties we have visited!"
United States
Alessio
The price is CA $177
CA $201 total
includes taxes & fees
Nov 2 - Nov 3
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
A large house with a swimming pool, surrounded by trees and a hilly landscape.

20. AgriHotel Villa Ambra

AgriHotel Villa Ambra
3.0 star property
Montepulciano
9.4 out of 10, Exceptional, (197 reviews)
"Nice hotel, friendly staff, good breakfast with custom made coffee"
Canada
Joanne
The price is CA $106
CA $123 total
includes taxes & fees
Oct 28 - Oct 29
AgriHotel Villa Ambra
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 5 hours ago
Hotel San Gregorio

Find out more about Pienza

Pienza Cottages information

Number of reviews
1,176
Accommodation
79 Cottages
Lowest Price
CA $116
Highest Price
CA $709

Frequently asked questions

How much do cottages in Pienza cost?
You'll pay between CA $116 and CA $709 per night for cottages in Pienza. No matter your budget, an ideal stay is just clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Pienza?
You'll find 79 cottages in Pienza. No matter if you're taking a trip with the kids or planning a retreat with your pals, Expedia can help you find the ideal space to immerse yourself in nature.
Why book your cottage in Pienza with Expedia?
Reserving a cottage in Pienza is as easy as clicking on your travel dates and selecting an ideal place for outdoor relaxation and recreation. From high-end retreats to affordable stays and cottages that include amenities like laundry facilities, Expedia has something for all tastes and styles. As for unbeatable deals? We've got your back!
How can I find cheap cottages in Pienza?
Expedia can help you easily source cheap cottages in Pienza. To book a fantastic stay in a couple of quick clicks, try out the filter tool to refine your search results by star rating, amenities and budget.
What is there to do in Pienza near my cottage?
You'll find plenty of awesome things to do and see in Pienza. Discover top attractions like Artemisia Gallery, Pienza Cathedral and Palazzo Comunale. Palazzo Piccolomini, Historic Centre of Pienza and Piazza Pio II also lure many visitors.

Explore a world of travel with Expedia