Title: Book the Best HISTORIC Hotels in Pienza in 2026 | Expedia.ca

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![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)

# Find Historic Hotels in Pienza from CA $139

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## Check availability on Pienza Historic Hotels

Tonight

[Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-29&endDate=2025-12-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pienza historic hotels

![Exterior](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/9a24ba4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/ad75fefb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/7290fd10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/e139d884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The house in the village - Angelica apartment - Vald'Orcia

[](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information)

Monticchiello

10/10

Exceptional

(11)

"Nice and comfortable house in a beautiful tiny village "

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

Lana A.

CA $143

CA $176 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/8477e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/9ee300f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/3f2e2df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/5d93306f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Il Focolare" Superior Apartment in Monticchiello

[](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information)

Monticchiello

10/10

Exceptional

(8)

"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "

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

Dan

CA $161

CA $196 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/9815a198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/ac6c76e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/ff5236c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double or Twin Room | View from room](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/fdc14dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Antico Granaione

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Antico-Granaione.h7778813.Hotel-Information)

Rapolano Terme

9.8/10

Exceptional

(60)

"old fashion building, clean and affordable"

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

Irene

CA $264

CA $297 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Antico-Granaione.h7778813.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room, Valley View | Bathroom](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/1ff7f88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/12f79b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/6bfc0883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Italia

[](https://www.expedia.ca/Cortona-Hotels-Hotel-Italia.h1663916.Hotel-Information)

Cortona Old Town

9.0/10

Wonderful

(289)

"The hotel amenities, comfort, hospitality are top notch. Should easily be a 4-star hotel! "

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

Neha

CA $192

CA $216 total

includes taxes & fees

Jan 17 - Jan 18, 2026

[](https://www.expedia.ca/Cortona-Hotels-Hotel-Italia.h1663916.Hotel-Information)

![Single Room, 1 Single Bed, Private Bathroom, City View | View from room](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6b57812f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Triple Room, Private Bathroom, City View | Exterior](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/fe6f317e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6bac2565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, Private Bathroom, City View | Bathroom](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6a93c509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### B&B San Francesco

[](https://www.expedia.ca/Cortona-Hotels-BB-San-Francesco.h23063422.Hotel-Information)

Cortona Old Town

8.8/10

Excellent

(55)

"The B&B is charming, the location is perfect, and Beatrice and the staff are so nice!"

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

Maria

[](https://www.expedia.ca/Cortona-Hotels-BB-San-Francesco.h23063422.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/093ed3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Breakfast area](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/17ae36fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/36720704.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

(94)

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

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

Sarah

CA $120

CA $139 total

includes taxes & fees

Jan 13 - Jan 14, 2026

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

![Sauna, hot tub, steam room, massages](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/025dd887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/b2055c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/0411b3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monastero di Cortona Hotel & Spa

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

Cortona Old Town

10/10

Exceptional

(255)

"Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return. "

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

Florence and Robert

CA $415

CA $463 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Interior](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/5ff3c1e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/644ef42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/4589cff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/e3578963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Gelda house, relax with a view

[](https://www.expedia.ca/Montalcino-Hotels-The-Gelda-House.h23275535.Hotel-Information)

Castelnuovo dell'Abate

9.6/10

Exceptional

(14)

"Loved our stay...lovely and quiet..great location "

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

Lisa K.

CA $161

CA $229 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Montalcino-Hotels-The-Gelda-House.h23275535.Hotel-Information)

![55-inch Smart TV with satellite channels, TV, Netflix](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/e99138c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free toiletries, hair dryer, bathrobes, slippers](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/28ba7ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Hot Tub](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/b824bd49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite | Bathroom](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/6b1f2619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palazzo Carletti

[](https://www.expedia.ca/Montepulciano-Hotels-Palazzo-Carletti.h3547611.Hotel-Information)

Montepulciano

9.8/10

Exceptional

(241)

"Excelente hotel."

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

jorge

[](https://www.expedia.ca/Montepulciano-Hotels-Palazzo-Carletti.h3547611.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/9d4ea066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, internet](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/2513fe04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/bbe8b3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/2598e840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

[](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information)

Siena

CA $9,630

CA $9,630 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.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=2026-01-12&endDate=2026-01-13&regionId=6023645&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Pienza Hotel Reviews

![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)

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

### Albergo San Biagio

10/10 Excellent

"gorgeous spot below the town, what an incredible view from the balcony "

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

![Hotel Santa Caterina](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540753/3b315dde_y.jpg)

### Hotel Santa Caterina

10/10 Excellent

"Amazing staff, great food and an even better view from the garden. "

[](https://expedia.ca/Siena-Hotels-Hotel-Santa-Caterina.h2540753.Hotel-Information)

![Castello di Velona Resort Thermal SPA & Winery](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/87359911_y.jpg)

### Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."

[](https://expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.Hotel-Information)

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg)

### Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "

[](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.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

"The room was beautiful and very clean. Breakfast staff was very kind."

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

## Frequently asked questions

### What can a history buff expect from a stay in Pienza?

### What's the best hotel in Pienza to learn about local history?

### How many historically relevant hotels are there in Pienza?

### What are the top historical places and other sights to visit in Pienza?

### What is a historic hotel like in Pienza?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Pienza have modern facilities?

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