Title: Pienza Vacation Rentals from CA $116: Short-Term Rentals for 2026 | Expedia.ca

[Pienza Travel Guide](https://expedia.ca/Pienza.dx6023645)[Hotels in Pienza](https://expedia.ca/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Flights to Pienza](https://expedia.ca/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.ca/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Pienza Car Rentals](https://expedia.ca/Car-Rentals-In-Pienza.d6023645.Car-Rental-Guide)[Pienza Vacation Packages](https://expedia.ca/Pienza.d6023645.Destination-Travel-Guides)

![Pienza showing a monument, a square or plaza and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pienza vacation rentals

![Food and drink](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double or Twin Room, 1 Bedroom](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/47a2d1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/882d4e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/4a89a1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel San Gregorio

[](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

Pienza

9.4/10

Exceptional

(134 reviews)

"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Mark

CA $202

CA $232 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

![Panoramic Cottage, 1 Bedroom | Exterior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/020483c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Cottage, 1 Bedroom](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/83ad69a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/a39f2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/6e2ad2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Affitacamere Maria Gabriella

[](https://www.expedia.ca/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

Pienza

9.8/10

Exceptional

(51 reviews)

"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lenise

CA $150

CA $206 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

![Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/4f1f04f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite Silvio al secondo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/884c0781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite Enea al primo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/04ed7e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite Bernardo, Panoramica al terzo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/8ce91a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PienzaLettings Suites

[](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information)

Pienza

10/10

Exceptional

(2 reviews)

"Fantastic room in the city center, close to everything in Pienza"

![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg)

Tom

CA $108

CA $126 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information)

![Monolocale Exclusive, vista città, secondo piano senza ascensore](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/f7106947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/cc713796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Monolocale Exclusive, vista città, secondo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/6be6d8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Monolocale Exclusive, vista città, secondo piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/4381c139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TuscanyLettings Studio&Room

[](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information)

Pienza

10/10

Exceptional

(1 review)

"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"

![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg)

keita

CA $131

CA $150 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1589x0y0-ab9335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/d953c731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Casa Olivieri, vista città, 1 piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/f32e69c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/5ded1ab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Gioia - Casa Olivieri 

[](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information)

Pienza

CA $119

CA $137 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/0263d307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/26e5f82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/f4cb97cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/bfee31ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Locanda di San Francesco

[](https://www.expedia.ca/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

Montepulciano

9.8/10

Exceptional

(133 reviews)

"Spotless, clean. Staff were friendly. Location and view was spectacular"

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Kim

CA $219

CA $248 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/0aaa13a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/8011dd87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, Balcony](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/2ef8f95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/cabc4072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Meublé Il Riccio

[](https://www.expedia.ca/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

Montepulciano

9.8/10

Exceptional

(87 reviews)

"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael.

[](https://www.expedia.ca/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

![Classic Apartment, 2 Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/9142c384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/2c20c3fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/bd01288a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/565416e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FonteLiving

[](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-FonteLiving.h15919621.Hotel-Information)

San Casciano dei Bagni

10/10

Exceptional

(6 reviews)

"Excellent experience, location, and environment."

![Taiwan](https://a.travel-assets.com/egds/marks/flags/tw.svg)

Chia-Hung

CA $98

CA $111 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-FonteLiving.h15919621.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/39e29e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/38f51959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/9c2d8838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 Double Bed | Living room](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/274ea02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Abbadia Sicille Relais

[](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

Trequanda

8.8/10

Excellent

(167 reviews)

"Room was beyond expectations. Helpful staff and overall great experience. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

CA $112

CA $129 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

![1 treatment room, massages](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/9867dcf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ba51ed0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ce312570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/7dd03bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casanova - Panoramic Rooms and Suites

[](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

San Quirico d'Orcia

9.2/10

Wonderful

(79 reviews)

"Fantastic place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Clifford

CA $267

CA $300 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

![Studio | Terrace/patio](https://images.trvl-media.com/lodging/124000000/123330000/123326000/123325917/7a189336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/124000000/123330000/123326000/123325917/372edad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123330000/123326000/123325917/e6dd0b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/124000000/123330000/123326000/123325917/546417d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Dimora di Dida

[](https://www.expedia.ca/Seggiano-Hotels-La-Dimora-Di-Dida.h123325917.Hotel-Information)

Seggiano

CA $118

CA $129 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/Seggiano-Hotels-La-Dimora-Di-Dida.h123325917.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/46c3ab32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/7dd80bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/f58a3308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/946f4e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bosco della Spina

[](https://www.expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

Murlo

9.6/10

Exceptional

(169 reviews)

"Views are amazing. Staff are very pleasant and helpful. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Maureen

CA $93

CA $116 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/ebbc46be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/bcab148b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/f199e1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite | Living area](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/35d091bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Locanda Di Cetona

[](https://www.expedia.ca/Cetona-Hotels-La-Locanda-Di-Cetona.h42239240.Hotel-Information)

Cetona

9.2/10

Wonderful

(5 reviews)

"A lovely hotel and very welcoming staff. Cetona is a delight. "

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Julian

[](https://www.expedia.ca/Cetona-Hotels-La-Locanda-Di-Cetona.h42239240.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/d732a716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room | Bathroom](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/8842009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/9d10099d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, Terrace](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/93858826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Piccola Locanda

[](https://www.expedia.ca/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

Chiusi

8.6/10

Excellent

(9 reviews)

"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffery

[](https://www.expedia.ca/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15880000/15872300/15872262/19ef0175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Double Room (Gli Orti)](https://images.trvl-media.com/lodging/16000000/15880000/15872300/15872262/75e7bce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15880000/15872300/15872262/4efc6252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Double Room (L'Orologio)](https://images.trvl-media.com/lodging/16000000/15880000/15872300/15872262/e537c142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### B&B Le Scalette di Piazza

[](https://www.expedia.ca/Montalcino-Hotels-BB-Le-Scalette-Di-Piazza.h15872262.Hotel-Information)

Montalcino

9.4/10

Exceptional

(90 reviews)

"Great location and excellent staff. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Jacek

[](https://www.expedia.ca/Montalcino-Hotels-BB-Le-Scalette-Di-Piazza.h15872262.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/12afb28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/1def40b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/a1afa9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residenza Fabroni

[](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

Montepulciano

8.8/10

Excellent

(96 reviews)

"gorgeous historical property, very attentive host, great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah

CA $107

CA $124 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/0d27663a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![22-inch TV with digital channels](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/5ed68d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, Jetted Tub | Deep soaking bathtub](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/188597d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/da2f0709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bed & Breakfast Vicolo dell'Oste

[](https://www.expedia.ca/Montepulciano-Hotels-Bed-Breakfast-Vicolo-DellOste.h4837070.Hotel-Information)

Montepulciano

9.6/10

Exceptional

(128 reviews)

"Great hosts, central location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander

[](https://www.expedia.ca/Montepulciano-Hotels-Bed-Breakfast-Vicolo-DellOste.h4837070.Hotel-Information)

![Suite Aria | Terrace/patio](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/17c800cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/6f74c993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/7ee71db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/96000000/95250000/95240100/95240092/4522b02a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Delcorto Suites

[](https://www.expedia.ca/Montepulciano-Hotels-Delcorto-Suites.h95240092.Hotel-Information)

Montepulciano

10/10

Exceptional

(34 reviews)

"Wonderful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rocio Q

CA $275

CA $309 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Montepulciano-Hotels-Delcorto-Suites.h95240092.Hotel-Information)

![Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5467h3644x6y6-bfae763b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/936c2188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/543e1f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5470h3644x0y0-9c1f6ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DormiVeglia B&B

[](https://www.expedia.ca/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information)

Monte San Savino

10/10

Exceptional

(27 reviews)

"Amazing, warm, sweet, lovely, such a gem of a place!"

![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg)

Melissa Hyun Joo

[](https://www.expedia.ca/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/001e488b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Living area](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/824e4462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Economy Double Room, 1 Double Bed, Private Bathroom](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/ba266d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Private kitchen](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/8c83167a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Idolina Guest House

[](https://www.expedia.ca/Montalcino-Hotels-Idolina-Guest-House.h9754480.Hotel-Information)

Montalcino

9.4/10

Exceptional

(105 reviews)

"The building is lovely - traditional Italian construction with big Chestnut beams in the ceiling. The owner/manager is very pleasant and helpful. Overall, a very nice place to stay. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Carl

[](https://www.expedia.ca/Montalcino-Hotels-Idolina-Guest-House.h9754480.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&regionId=6023645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

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Private vacation homes

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT)

Residences

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Aparthotels

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CHALET)

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## Top Pienza Hotel Reviews

![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg)

### Fonteverde Lifestyle & Thermal Retreat

10/10 Excellent

"The spa was refreshing and dinning was wonderful and the service was amazing both at dinner and breakfast. "

[](https://expedia.ca/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.Hotel-Information)

![Albergo San Biagio](https://images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/c85acee6_y.jpg)

### Albergo San Biagio

10/10 Excellent

"Muy amable "

[](https://expedia.ca/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.Hotel-Information)

![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg)

### Monastero di Cortona Hotel & Spa

10/10 Excellent

"Everything was great! Lovely hotel "

[](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information)

![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg)

### Hotel Relais II Chiostro di Pienza

10/10 Excellent

"A little tired, extremely clean, with an amazing staff"

[](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information)

![Grand Hotel Terme](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289175/3fd53b10_y.jpg)

### Grand Hotel Terme

10/10 Excellent

"Clean room and friendly staff"

[](https://expedia.ca/Chianciano-Terme-Hotels-Grand-Hotel-Terme.h1289175.Hotel-Information)

![Hotel Certosa Di Maggiano](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5_y.jpg)

### Hotel Certosa Di Maggiano

10/10 Excellent

"The best in Siena."

[](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information)

![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/8b3fbbcc_y.jpg)

### Relais Villa Grazianella - UNA Esperienze

10/10 Excellent

"Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!"

[](https://expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information)

![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg)

### Hotel Corsignano

10/10 Excellent

"Wonderful stay. Very welcoming staff and check in was quick and simple. Very convenient as parking provided. Room was spacious especially bathroom with great bathtub Breakfast was perfect"

[](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information)

![Rosewood Castiglion del Bosco](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a_y.jpg)

### Rosewood Castiglion del Bosco

10/10 Excellent

"Wonderful stay "

[](https://expedia.ca/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.Hotel-Information)

## Find out more about Pienza

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pienza. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

## Frequently asked questions

### Can I find a vacation rental in Pienza?

### What are some of the best vacation home rentals in Pienza?

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### What’s a vacation rental in Pienza like?

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