Title: Cortona Vacation Home Rentals from CA $127: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[Cortona Travel Guide](https://expedia.ca/Cortona.dx601360)[Hotels in Cortona](https://expedia.ca/Cortona-Hotels.d601360.Travel-Guide-Hotels)[Vacation Rentals in Cortona](https://expedia.ca/Cortona-Vacation-Rentals.d601360.Travel-Guide-VacationRentals)[Flights to Cortona](https://expedia.ca/Cheap-Flights-To-Cortona.d601360.Travel-Guide-Flights)[Things to do in Cortona](https://expedia.ca/Things-To-Do-In-Cortona.d601360.Travel-Guide-Activities)[Cortona Car Rentals](https://expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide)[Cortona Vacation Packages](https://expedia.ca/Cortona.d601360.Destination-Travel-Guides)

![Cortona showing a city and farmland](https://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Cortona Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Cortona Vacation Homes

![Property grounds](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/0248fcc9.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)

![Interior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/63933730.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)

### Vacation Home in Cortona

CA $114

CA $150 total

includes taxes & fees

Nov 30 - Dec 1

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

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/0cf49d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/ae9cfe4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/w636h611x0y0-ad5cabc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/dd03f600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fratticciola

10/10

Exceptional

(1)

"Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. "

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

Nancy F.

CA $146

CA $176 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Cortona-Hotels-House-In-The-Cortona-Countryside.h39951786.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/e6444fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/d67b4cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/a1ed5b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/c583fb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cortona

8.0/10

Very good

(1)

"Pros: Authentiek Toscaanse boerderij ( wij hadden de bovenste etage) met prachtige tuin en lekker zwembad met mooi uitzicht. De gastheer Angelo was top en de Toscaanse diners waren onvergetelijk. Bedankt dat ik mijn verjaardag zo heb mogen vieren. Hele mooie herinnering. Pizza’s bakken was ook een feest. Ook heel fijn dat er een airco was. Onze 4 puber jongens hebben zich prima vermaakt en leuk dat er nog andere gasten zijn uit andere appartementen die je dan ziet op hetToscaanse diner. Top...

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

Anonymous traveller

CA $179

CA $185 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Cortona-Hotels-Apartment-La-Vecchia-Fornace-La-Terrazza-With-Shared-Pool-Wi-Fi.h89137839.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)

![Fridge, oven, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/90-47ebfe31.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)

### Vacation Home in Montecchio

9.0/10

Wonderful

(2)

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

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

Monica S.

CA $98

CA $127 total

includes taxes & fees

Nov 29 - Nov 30

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

![Interior](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/27c749dd.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)

![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)

### Vacation Home in Toscana

9.0/10

Wonderful

(2)

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

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

Lisa C.

[](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)

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

![Exterior](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/934c21df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in 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 "

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

RAUL

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

![Interior](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/68e32b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![10 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/c265586f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/6c76c280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/c7047ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in perugia

10/10

Exceptional

(1)

"Pros: Great hosts, who were super helpful and responsive. Beautiful house and gardens. Cons: Nothing - it was great!"

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

Anonymous traveller

CA $4,088

CA $4,337 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Perugia-Hotels-Holiday-Home-Palazzetto-Bovini-With-Wi-Fi-And-Private-Pool.h102651128.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/0459e4ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/e00d1488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/47257042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/8c44b07b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arezzo

CA $132

CA $181 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Arezzo-Hotels-Dolce-Casa-2-Summary.h92018366.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)

![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)

![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)

### Vacation Home in 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! "

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

Rob C.

CA $351

CA $486 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chianciano-Terme-Hotels-MONTEPULCIANO-A-DUE-PASSI-DALLA-VAL-DORCIA.h84515383.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/ddcd9ce4.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)

### Vacation Home in 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! "

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

Graham S.

CA $234

CA $277 total

includes taxes & fees

Nov 30 - Dec 1

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

![Outdoor dining](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/5e0bf0da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/7812a5c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/90daa8d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/b46bdfd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Castel Rigone

10/10

Exceptional

(3)

"The only thing this place could have that it doesn't is an infinity pool! We loved it here. It was a last minute booking and the host was super helpful. STUNNING views from the patio, and the lake is a short drive down the hill. Also, a very cool little town with restaurants just a two minute drive.Our favorite stays in Italy we're in these little remote towns. Soooo nice. "

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

Adam H.

CA $151

CA $187 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Passignano-Sul-Trasimeno-Hotels-Vrbo-Property.h97072488.Hotel-Information)

![TV, DVD player](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/fc2934d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/501031f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/269ff2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/28d9ff3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Toscana

CA $8,135

CA $9,095 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h68051629.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)

![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/40000000/39870000/39866200/39866124/62b86b12.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)

### Vacation Home in 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)....

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

Heike K.

CA $132

CA $280 total

includes taxes & fees

Nov 30 - Dec 1

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

![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)

![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/9ee300f7.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)

### Vacation Home in 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 $155

CA $187 total

includes taxes & fees

Dec 1 - Dec 2

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

![Comfort Apartment, 3 Bedrooms | View from property](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/13a35e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment, 3 Bedrooms | Pool](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/ca9a6ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment, 3 Bedrooms | Exterior](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/97c318ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, 3 Bedrooms | Reception](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/c0f945f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Città di Castello

CA $407

CA $448 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Citta-Di-Castello-Hotels-Rustic-Holiday-Home-In-Citta-Di-Castello-With-Swimming-Pool.h109332831.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89870000/89861100/89861029/1af91144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89870000/89861100/89861029/68a74520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89870000/89861100/89861029/8473f9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89870000/89861100/89861029/a7224fe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sinalunga

8.0/10

Very good

(2)

"It seemed like a beautiful spot,but ws had tocancel at the last minute due to illness. I hope we can reschedule some day."

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

Robert R.

CA $190

CA $221 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Sinalunga-Hotels-Pretty-Outbuilding-With-Private-Park.h89861029.Hotel-Information)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/d34ca53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/37bf5d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/4b1aa390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/c83ae3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monterongriffoli

CA $220

CA $342 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Montalcino-Hotels-Vrbo-Property.h114488726.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111560000/111557300/111557292/5c357c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111560000/111557300/111557292/eebdef33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111557300/111557292/6e693c8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111560000/111557300/111557292/471fe63c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Ramazzano - Le Pulci

CA $160

CA $194 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Perugia-Hotels-Vrbo-Property.h111557292.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/88000000/87730000/87726500/87726433/edb4637f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87730000/87726500/87726433/9391bcd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87730000/87726500/87726433/7258305f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87730000/87726500/87726433/c1e3c545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Umbertide

8.0/10

Very good

(1)

"Pros: Location in the mountains is superb, very friendly& supportive staff, fair price Cons: Only very small windows in the appartment, thus dark and nearly no chance for fresh cold air in the night. Due to the size of the location the pool was overcrowded and too less sun chairs. Photos better than reality."

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

Anonymous traveller

CA $175

CA $294 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Umbertide-Hotels-Apartment-Lavanda-Ad-Antico-Casale-700-With-Shared-Pool-Wi-Fi.h87726433.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/2e5fc023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/708c8021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/3d8fec8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/4f08693d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in montalcino

CA $244

CA $555 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Montalcino-Hotels-Agritourism-In-Val-Dorcia.h91782207.Hotel-Information)

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## Find vacation rentals that suit your style

Villas

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Aparthotels

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Cottages

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Residences

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Condos

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Chalets

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## Top Cortona Hotel Reviews

![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

"Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally got to our amazing suite and befriending two amazing individuals in the hotel bar. The roof top suite was absolutely amazing! The room is quiet, private and much larger than described on the site. We absolutely loved the room and the privacy. The rooftop suite is the best in the house! Claudio in the bar and Salvatore the sommelier are stellar to guests, they turned around the entire experience! I let them know what had happened upon arrival and they immediately got the GM to reach out to us. Lara, the GM is amazing and quickly made our experience turn into something so special, as we wanted! She is an incredible woman and turned our stay into an incredible experience! The breakfast is nothing less than wonderful and the service in their restaurants are so attentive and the food was delicious. Hands down, I would love to go back again. They certainly made things right by making our romantic stay, exactly what I wanted. They made us feel heard and valued and welcomed at this once in a lifetime experience. We made friends that we will cherish and memories that we will never forget! Claudio, Lara and Salvatore really made our stay exactly what we needed and wanted! "

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

![Hotel Villa Marsili](https://images.trvl-media.com/lodging/1000000/930000/922700/922648/c5455b25_y.jpg)

### Hotel Villa Marsili

10/10 Excellent

"Most comfortable room and bed beds that we stayed in the whole time we were in Italy! Also, the breakfast was 10 out of 10! Much better than the five star hotel that we stayed at in Rome and Florence. "

[](https://expedia.ca/Cortona-Hotels-Hotel-Villa-Marsili.h922648.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e_y.jpg)

### Hotel Italia

10/10 Excellent

"The personnel were warm and accommodating. The breakfast was amazing! The views were wonderful!"

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

![Il Falconiere - Relais e Chateaux](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/2334a48c_y.jpg)

### Il Falconiere - Relais e Chateaux

10/10 Excellent

"What an incredible stay at Il Falconiere! Exceptional service and unforgettable experiences — from Silvia Baracchi’s amazing cooking class to an unbelievable dinner at the Michelin-starred restaurant. Breakfast in the glass room overlooking the Tuscan hills was pure magic. We loved wandering through Cortona — charming streets, fantastic restaurants, and surprisingly great shopping. Already dreaming of our next visit! "

[](https://expedia.ca/Cortona-Hotels-Relais-Il-Falconiere.h528472.Hotel-Information)

![B&B Piccolo Hotel](https://images.trvl-media.com/lodging/13000000/12240000/12234700/12234603/ab339a34_y.jpg)

### B&B Piccolo Hotel

10/10 Excellent

"We were able to drive up to the door and leave our car with staff. Staff was amazing. Breakfast had many options and always replenished. It is right off the main piazza. Would stay again for sure!"

[](https://expedia.ca/Cortona-Hotels-BB-Piccolo-Hotel.h12234603.Hotel-Information)

![Locanda agli Amici](https://images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/5a958be8_y.jpg)

### Locanda agli Amici

10/10 Excellent

"Very clean and beautiful room. Amazing views! Breakfast and staff were the best!"

[](https://expedia.ca/Cortona-Hotels-Locanda-Agli-Amici.h90300548.Hotel-Information)

![Luxury Cortona view hilltop Villa](https://images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/73d0cc6c_y.jpg)

### Luxury Cortona view hilltop Villa

10/10 Excellent

"Beautiful villa of your dreams on a hillside near Cortona. Everything was exactly as described and the villa is very large. We had 4 couples each in the 4 master bedrooms which are huge and very nicely separated. Be aware the road up to the villa is very challenging! This is not walking distance or walkable to anything but within 10-15 minutes to Cortona. Not a problem for us at all. Very quiet, very beautiful, fantastic location to explore Tuscany and Umbria. Very large kitchen! We had the team there prepare us all a dinner one night and it was one of our favorite meals of the entire trip."

[](https://expedia.ca/Cortona-Hotels-Luxury-Cortona-View-Hilltop-Villa.h28840420.Hotel-Information)

![Cortona Resort Spa](https://images.trvl-media.com/lodging/101000000/100780000/100776500/100776429/55c67d9d_y.jpg)

### Cortona Resort Spa

8/10 Good

"Needs lotion in the guest rooms and towels. The staff was wonderful. So was the food. "

[](https://expedia.ca/Cortona-Hotels-Cortona-Resort-Spa.h100776429.Hotel-Information)

## Find out more about Cortona

## Cortona Vacation Homes information

| Number of reviews | 25 |
| --- | --- |
| Accommodation | 235 Vacation Homes |
| Lowest Price | CA $127 |
| Highest Price | CA $9,095 |

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-   [Farmstay in Val d'Orcia](https://www.expedia.ca/Val-DOrcia-Agritourism.d6047918-aaAgritourism.Travel-Guide-Accommodation)
-   [Vacation Homes in Val d'Orcia](https://www.expedia.ca/Val-DOrcia-Private-Vacation-Homes.d6047918-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Hotels near Valdichiana Outlet Village](https://www.expedia.ca/Valdichiana-Outlet-Village-Hotels.0-l6153160-0.Travel-Guide-Filter-Hotels)
-   [Valiano Hotels](https://www.expedia.ca/Valiano-Hotels.d6047297.Travel-Guide-Hotels)

-   [Flights from Terontola](https://www.expedia.ca/lp/flights/6025579/flights-from-terontola)
-   [Flights from Valiano](https://www.expedia.ca/lp/flights/6047297/flights-from-valiano)
-   [Flights from Marciano della Chiana](https://www.expedia.ca/lp/flights/6285674/flights-from-marciano-della-chiana)
-   [Flights from Sodo](https://www.expedia.ca/lp/flights/6361280/flights-from-sodo)

-   [Visit Camucia](https://www.expedia.ca/Camucia.dx6289367)
-   [Visit Creti](https://www.expedia.ca/Creti.dx3000439377)
-   [Visit Marciano della Chiana](https://www.expedia.ca/Marciano-Della-Chiana.dx6285674)
-   [Visit Mercatale di Cortona](https://www.expedia.ca/Mercatale-Di-Cortona.dx601101)
-   [Visit Metelliano](https://www.expedia.ca/Metelliano.dx553248635975868789)
-   [Visit Montagnano](https://www.expedia.ca/Montagnano.dx6361223)
-   [Visit Montepulciano Stazione](https://www.expedia.ca/Montepulciano-Stazione.dx6285775)
-   [Visit Ossaia](https://www.expedia.ca/Ossaia.dx6361235)
-   [Visit Portole](https://www.expedia.ca/Portole.dx3000390328)
-   [Visit Potassa](https://www.expedia.ca/Potassa.dx6361322)
-   [Visit Rigutino](https://www.expedia.ca/Rigutino.dx6361226)
-   [Visit San Pietro a Cegliolo](https://www.expedia.ca/San-Pietro-A-Cegliolo.dx6130155)
-   [Visit Sinalunga](https://www.expedia.ca/Sinalunga.dx603293)
-   [Visit Tegoleto](https://www.expedia.ca/Tegoleto.dx3000708346)
-   [Visit Terontola](https://www.expedia.ca/Terontola.dx6025579)

-   [Car rental Castiglion Fiorentino](https://www.expedia.ca/Car-Rentals-In-Castiglion-Fiorentino.d6047858.Car-Rental-Guide)
-   [Car rentals near Cortona Old Town](https://www.expedia.ca/Car-Rentals-In-Cortona-Old-Town.d553248633938945259.Car-Rental-Guide)
-   [Car rental Mercatale di Cortona](https://www.expedia.ca/Car-Rentals-In-Mercatale-Di-Cortona.d601101.Car-Rental-Guide)
-   [Car rental Montepulciano Stazione](https://www.expedia.ca/Car-Rentals-In-Montepulciano-Stazione.d6285775.Car-Rental-Guide)
-   [Car rental Terontola](https://www.expedia.ca/Car-Rentals-In-Terontola.d6025579.Car-Rental-Guide)
-   [Car rental Torrita di Siena](https://www.expedia.ca/Car-Rentals-In-Torrita-Di-Siena.d6046345.Car-Rental-Guide)

-   [Things to do in Brolio](https://www.expedia.ca/Things-To-Do-In-Brolio.d6361222.Travel-Guide-Activities)
-   [Things to do in Lucignano](https://www.expedia.ca/Things-To-Do-In-Lucignano.d6048408.Travel-Guide-Activities)
-   [Things to do in Terontola](https://www.expedia.ca/Things-To-Do-In-Terontola.d6025579.Travel-Guide-Activities)

-   [Book Vacation Homes in Cortona on Expedia.it](https://www.expedia.it/Cortona-Case-Vacanze-Private.d601360-aaCaseVacanzePrivate.Guida-Viaggi-Alloggi)