Title: Pienza Vacation Home Rentals from CA $126: Search Top Private Vacation Homes for Rent | Expedia.ca

  

[Pienza Travel Guide](https://expedia.ca/Pienza.dx6023645)[Hotels in Pienza](https://expedia.ca/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Vacation Rentals in Pienza](https://expedia.ca/Pienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals)[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://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157955-Pienza.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Pienza Vacation Rentals

![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)

### 

Change your mind

Book hotels with free cancellation

![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)

### 

Treat yourself

Sign in to save 10% or more on thousands of hotels

[Sign in](https://www.expedia.ca/login)

![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)

### 

Be picky

Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

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

In four months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Pienza Vacation Homes

![Interior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/8477e2d7.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)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/a8b308d2.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)

### "Il Focolare" Superior Apartment in Monticchiello

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! "

CA $162

CA $195 total

includes taxes & fees

Oct 14 - Oct 15

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

![Exterior](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/1be9ea28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/13f32ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/7838807c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, 3 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/24020f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Agriturismo San Filippo

Acquapendente

9.0/10

Wonderful

(13)

"Excellent experience!"

CA $132

CA $146 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Acquapendente-Hotels-Agriturismo-San-Filippo.h31527256.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205642/0a829d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205642/888cd544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom, Garden View](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205642/2eff6465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom, Garden View | Private kitchen](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205642/cafbfe61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Le Roghete

Acquapendente

9.4/10

Exceptional

(3)

"The address of the hotel was wrong on the Hotels.com web site. After an anxious hour or so our host was kind enough to come and get us, we were on foot walking the Via Francigena and the additional 4 miles back would have been a killer. Our host arranged for a cab the next morning so we were back on schedule. Worth the cab expense to keep on schedule. Wonderful evening meal and a great hotel. I would visit it again."

CA $131

CA $145 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Acquapendente-Hotels-Le-Roghete.h35205642.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/b1c6eafc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/6475a598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/0b446d0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/8f1a6a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eva's house awaits you!

Monterubiaglio

10/10

Exceptional

(2)

"L'appartement est très grand (rez-de-chaussée d'une maison) et aménagé avec bcp de goût. Tout etait fournis à l'arrivée : linges de lit, serviettes de toilette, liquide vaisselle, éponge et torchons. L'accueil des propriétaires etaient chaleureux et leurs conseils bienvenus. Chien, chat, tortues nous ont réservés un acceuil amical. Le jardin est très grand, idéal lorsqu'on a des enfants. La piscine est un avantage non négligeable au vu des températures très élevées. Les villages villes...

CA $162

CA $191 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Castel-Viscardo-Hotels-Evas-House-Awaits-You.h37593856.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)

![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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/d909396a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Gelda house, relax with a view

Castelnuovo dell'Abate

9.6/10

Exceptional

(13)

"We loved the village setting and the apartment was very comfortable and well appointed."

CA $162

CA $230 total

includes taxes & fees

Oct 24 - Oct 25

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

![Outdoor pool](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/3d55d541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/d70cff47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/27c749dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/11c868e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Falco- Cignella Resort Tuscany

Toscana

9.0/10

Wonderful

(2)

"Perfectly located in the center of the Heart of Tuscany. Great property with a clean and spacious interior. "

CA $8,107

CA $9,085 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Trequanda-Hotels-Villa-Falco-Cignella-Resort-Tuscany.h68049942.Hotel-Information)

![Interior entrance](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/373c757f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Spa](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/9f5a336b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/05f902c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/35c81468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Poggio del Sole

Castiglione del Lago

8.0/10

Very good

(4)

"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "

CA $249

CA $278 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Castiglione-Del-Lago-Hotels-Poggio-Del-Sole.h19986371.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/6a2b762c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/905084fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/a009fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/f6f7b43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eagle House

CHIANCIANO

10/10

Exceptional

(3)

"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "

CA $336

CA $475 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Chianciano-Terme-Hotels-MONTEPULCIANO-A-DUE-PASSI-DALLA-VAL-DORCIA.h84515383.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/2419483e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/013b1ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/456c8609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/d1a6db77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Tuscan-style apartment Suitable for families. Pets allowed

Toscana

10/10

Exceptional

(1)

"Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "

CA $211

CA $266 total

includes taxes & fees

Oct 15 - Oct 16

[](https://www.expedia.ca/Siena-Hotels-Vrbo-Property.h114180505.Hotel-Information)

![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/054b2390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/f3230669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/c86b0ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/2df8f8f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MDQ Events - A natural oasis on the Via Francigena

catiglione d'orcia

CA $136

CA $186 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Castiglione-DOrcia-Hotels-MDQ-Events-A-Natural-Oasis-On-The-Via-Francigena.h36359627.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/f746b6f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/fc018cfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/640c0207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/e9d49b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Independent house in the historic center

CASTIGLIONE D'ORCIA

9.4/10

Exceptional

(9)

"Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! "

CA $233

CA $277 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Castiglione-DOrcia-Hotels-Independent-House-In-The-Historic-Center.h18976608.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8def11f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/26d5f3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8e2d77d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/5d163297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The House of Alice, charm and relaxation

Montalcino (SI)

9.8/10

Exceptional

(66)

"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "

CA $259

CA $350 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/0248fcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/35d33457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/20f3f653.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/93000000/92360000/92355700/92355622/ee21b4e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday home with panoramic terrace ideal for families and couples

Cortona

CA $114

CA $149 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Cortona-Hotels-Holiday-Home-With-Panoramic-Terrace-Ideal-For-Families-And-Couples.h92355622.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/ec9bd8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/a978fac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/cb24f428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/ff617fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Exclusive Stone Tower.

Casciano

9.6/10

Exceptional

(5)

"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...

CA $144

CA $242 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/a26282ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/007fccea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/85461a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon House, Kitchen, Hill View | Living area](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/e02bdbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zampugna

Trequanda

9.2/10

Wonderful

(5)

"Beautiful and host is great!"

CA $650

CA $720 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Trequanda-Hotels-Zampugna.h21136264.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/b5d9a4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/47f3dce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/ad4e5fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/7ed60a74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Romantic farm in the Sienese hills

Trequanda, Siena

"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....

CA $131

CA $284 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/e63ddb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/13261dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/38757a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/0f4b4ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Casetta di Brunello, quiet and breathtaking views

Montalcino

9.6/10

Exceptional

(16)

" Beautiful!"

CA $259

CA $350 total

includes taxes & fees

Oct 24 - Oct 25

[](https://www.expedia.ca/Montalcino-Hotels-La-Casetta-Di-Brunello.h36077744.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/4c9dc305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/ea734e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/f92088fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/90-1ae59b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montecchio di Cortona

Montecchio

9.0/10

Wonderful

(2)

"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."

CA $97

CA $126 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Cortona-Hotels-Montecchio-Di-Cortona.h32631932.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/246e837e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/648e852d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/44ba8701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books, computer monitors](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/2f33fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Domotic Suite at Villa Anna

Buonconvento

CA $117

CA $218 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Buonconvento-Hotels-Vrbo-Property.h105089096.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/313fd19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/65902230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/78a1bea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/d4c6880a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The crete senesi

Asciano

10/10

Exceptional

(1)

"Une très belle location dans l'environnement magique de la campagne toscane, Paolo est très accueillant , seul bémol la proximité de la route."

CA $243

CA $263 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Asciano-Hotels-Vrbo-Property.h106819737.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=2025-10-25&endDate=2025-10-26&regionId=6023645&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPienza-Private-Vacation-Homes.d6023645-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPienza-Private-Vacation-Homes.d6023645-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Pienza Hotel Reviews

![Hotel San Gregorio](//images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3_y.jpg)

### Hotel San Gregorio

10/10 Excellent

"Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer."

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

![Tenuta Santo Pietro](//images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/4fa44438_y.jpg)

### Tenuta Santo Pietro

10/10 Excellent

"Great countryside stay"

[](https://expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information)

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

### Hotel Relais II Chiostro di Pienza

10/10 Excellent

"The perfect location. Gorgeous property. Excellent breakfast. "

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

![Hotel Certosa Di Maggiano](//images.trvl-media.com/lodging/1000000/530000/528500/528470/4c3dd1ab_y.jpg)

### Hotel Certosa Di Maggiano

10/10 Excellent

"A wonderfully peaceful hotel in the middle of Tuscany. Amazing views. Great staff - friendly, professional and very helpful & accommodating. "

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

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

### Fonteverde Lifestyle & Thermal Retreat

10/10 Excellent

"Fine"

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

![Nuovo Etruria Resort](//images.trvl-media.com/lodging/114000000/113750000/113748300/113748275/5960f205_y.jpg)

### Nuovo Etruria Resort

10/10 Excellent

"Such an oasis of calm and relaxation. The room was large and cool with a very comfortable bed. The pool was beautiful and very refreshing. The staff were very friendly and helpful. A wonderful setting and just a short walk from the beautiful town and many fantastic restaurants. Would definitely recommend this hotel to others visiting Montepulciano."

[](https://expedia.ca/Montepulciano-Hotels-Nuovo-Etrurua-Resort.h113748275.Hotel-Information)

![Precise Tale Poggio Alla Sala](//images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/8fbdd5cc_y.jpg)

### Precise Tale Poggio Alla Sala

10/10 Excellent

"Property is very well maintained with amazing views. The main building is gorgeous with a beautiful dining area. Overall an amazing experience and one i really want to repeat"

[](https://expedia.ca/Montepulciano-Hotels-Precise-Tale-Poggio-Alla-Sala.h90888666.Hotel-Information)

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

### Monastero di Cortona Hotel & Spa

10/10 Excellent

"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"

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

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

### Hotel Corsignano

10/10 Excellent

"Wonderful hotel! Beautiful, very clean, staff was great, friendly and helpful. Perfect location for seeing the town and hiking to amazing views. Loved it!"

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

## Find out more about Pienza

## Pienza Vacation Homes information

| Number of reviews | 118 |
| --- | --- |
| Accommodation | 1164 Vacation Homes |
| Lowest Price | CA $126 |
| Highest Price | CA $9,085 |

## Explore a world of travel with Expedia

-   More ways to book

-   [Book Vacation Homes in Pienza on Expedia.it](https://www.expedia.it/Pienza-Case-Vacanze-Private.d6023645-aaCaseVacanzePrivate.Guida-Viaggi-Alloggi)