Title: Chianti Region Vacation Rentals from CA $158: Short-Term Rentals for 2026 | Expedia.ca

[Chianti Region Travel Guide](https://expedia.ca/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.ca/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides)

![Fontebranda](https://images.trvl-media.com/place/553248621532500698/e60fe766-dca8-4e89-8ca2-89967b23ad65.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Chianti Region Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 12 - Jan 13](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-12&endDate=2026-01-13&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-13&endDate=2026-01-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=603148&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)

## Our top choices for Chianti Region vacation rentals

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/3db308c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/45947cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 1 Bedroom, Non Smoking, Kitchen](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/61db7f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 1 Bedroom, Non Smoking, Kitchen | Living area](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/bdde45d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Rocca-Palazzaccio.h39673326.Hotel-Information)

9.0/10

Wonderful

(14 reviews)

"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...

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

Lauren

CA $125

CA $342 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Impruneta-Hotels-Rocca-Palazzaccio.h39673326.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/b50d05a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Steam room, Turkish bath, body scrubs, massages](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/e763d814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Loro Ciuffenna

[](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information)

9.4/10

Exceptional

(23 reviews)

"The staff were great and the villa was amazing"

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

Ralphvincent

CA $166

CA $183 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/fd869ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/d7d83723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/01ed134f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/b9b003bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Casciano in Val di Pesa

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information)

9.2/10

Wonderful

(82 reviews)

"It was a wonderful stay the bed was comfortable and the view was beautiful. "

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

Ruben

CA $159

CA $182 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/994aad7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, soundproofing, free WiFi](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/2b26409c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/ddbdc210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/735b790e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Gaiole in Chianti

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information)

10/10

Exceptional

(12 reviews)

"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."

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

Perry

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information)

![Panoramic Apartment (2) | Terrace/patio](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/975fa997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Apartment](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/4140baee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/36cba6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/df81ebe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-Vacanze-Squarcialupi.h42405254.Hotel-Information)

8.8/10

Excellent

(3 reviews)

"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "

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

Jeffrey

CA $160

CA $186 total

includes taxes & fees

Feb 7 - Feb 8

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-Vacanze-Squarcialupi.h42405254.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/1f917275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Studio, Valley View | Living area](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/59370526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/848fae17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Studio, Valley View](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/14afd628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Certaldo Alto

[](https://www.expedia.ca/Certaldo-Hotels-Borgo-Antico-Residence.h110872226.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Great place to relax take in the local culture and enjoy Tuscany."

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

jane

CA $104

CA $160 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Certaldo-Hotels-Borgo-Antico-Residence.h110872226.Hotel-Information)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/f58917b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Duplex, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/cbaa7c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/0c1e54bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/9c14d908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Greve in Chianti

[](https://www.expedia.ca/Greve-In-Chianti-Hotels-Terre-Di-Baccio.h23183851.Hotel-Information)

9.8/10

Exceptional

(71 reviews)

"The stay was great, and the staff were wonderful. "

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

SYDNEY

CA $442

CA $493 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Greve-In-Chianti-Hotels-Terre-Di-Baccio.h23183851.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/967d2c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/ddee21d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/f623ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/4f478603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Barberino Tavarnelle

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Antica-Pieve-BB.h971821.Hotel-Information)

9.4/10

Exceptional

(14 reviews)

"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "

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

Jessica

CA $125

CA $176 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Antica-Pieve-BB.h971821.Hotel-Information)

![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/59068004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 1 Bedroom, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/c907c444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast meal](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/1d36a1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/727e0d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Figline e Incisa Valdarno

[](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information)

9.2/10

Wonderful

(70 reviews)

"Very nice place"

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

Maria

CA $142

CA $158 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/265e303f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/b0f5db83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/a1551d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/8275ba4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Colle di Val d'Elsa

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Sportland.h95247428.Hotel-Information)

7.2/10

Good

(5 reviews)

"Struttura essenziale ed economica "

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

Giorgio

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Sportland.h95247428.Hotel-Information)

![Panoramic Apartment](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/de61baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/b87dac4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Apartment](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/ac22c4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/f41ed065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Residence-Il-Connubio.h3620731.Hotel-Information)

8.8/10

Excellent

(32 reviews)

"Such a cute little place! Very clean and easy to get around! Would highly recommend!"

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

Desiree

[](https://www.expedia.ca/Impruneta-Hotels-Residence-Il-Connubio.h3620731.Hotel-Information)

![Family Apartment, 2 Bedrooms, Hill View, Tower | View from room](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/d8d59316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment, 2 Bedrooms, Non Smoking, Tower | Living area](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/24daf1d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/bd8eeebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/2872b783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Pergine Valdarno

[](https://www.expedia.ca/Pergine-Valdarno-Hotels-Casa-Vacanze-Le-Fornaci.h101930876.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."

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

Gregory

CA $178

CA $201 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Pergine-Valdarno-Hotels-Casa-Vacanze-Le-Fornaci.h101930876.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/4c3be6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served, Italian cuisine, alfresco dining ](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/bfbda0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/c9ef69ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/36dbdc56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Casciano in Val di Pesa

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information)

9.6/10

Exceptional

(97 reviews)

"Great people, great location great service"

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

James

CA $190

CA $216 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/df1d957c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Duplex, 2 Bedrooms (Mimosa) | Living area](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/0b31f6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/343d0b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/c2de7201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information)

9.4/10

Exceptional

(9 reviews)

"Very nice agriturismo. "

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

Ruth

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/52973642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/003afa33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/823021fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 Double Bed (2 adults)](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/9d79efbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Barberino Tavarnelle

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Chianti-Village-Morrocco.h5273860.Hotel-Information)

8.6/10

Excellent

(111 reviews)

"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "

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

Richard

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Chianti-Village-Morrocco.h5273860.Hotel-Information)

![Apartment | Exterior](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/59e23101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Interior](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/15ad5902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Dining](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/22f499bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Interior](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/ff0d3da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Barberino Tavarnelle

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Beautiful-Apartment-In-Chianti.h89179420.Hotel-Information)

CA $620

CA $757 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Beautiful-Apartment-In-Chianti.h89179420.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a64418f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/e1962a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/de3fa368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, body treatments, body wraps, body scrubs](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a7311095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Casciano in Val di Pesa

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information)

9.4/10

Exceptional

(25 reviews)

"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"

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

Raymundo

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information)

![Deluxe Room, City View](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/db32679d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/c24bbc8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/c2f130ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, City View](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/6615ccb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Historic Centre of Florence

[](https://www.expedia.ca/Florence-Hotels-Maison-Ginori-Guelfa.h104540885.Hotel-Information)

10/10

Exceptional

(21 reviews)

"We loved everything about Maison Ginori Guelfa, from our host, our room and how close the walking distance to the center of the city."

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

Janet

CA $226

CA $269 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Florence-Hotels-Maison-Ginori-Guelfa.h104540885.Hotel-Information)

![Family Triple Room](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/afd8d18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/214c6915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/f2f7037e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/c1de9144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Historic Centre of Florence

[](https://www.expedia.ca/Florence-Hotels-Residenza-La-Musa-Amarcord.h19722799.Hotel-Information)

9.8/10

Exceptional

(153 reviews)

"Room was large & well appointed. Bathroom was new with update products. Staff was great."

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

John

CA $130

CA $163 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Florence-Hotels-Residenza-La-Musa-Amarcord.h19722799.Hotel-Information)

![Deluxe Double Room, City View | Room amenity](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/ce1860bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/ddd6b897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room, City View](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/ada72939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/e98a98d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Historic Centre of Florence

[](https://www.expedia.ca/Florence-Hotels-San-Giuliano-Inn.h19411651.Hotel-Information)

10/10

Exceptional

(406 reviews)

"Great inn. "

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

Carol

CA $128

CA $161 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Florence-Hotels-San-Giuliano-Inn.h19411651.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=2026-01-26&endDate=2026-01-27&regionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=VILLA)

Apartments

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Residences

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=CHALET)

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## Top Chianti Region Hotel Reviews

![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16_y.jpg)

### Villa Casagrande Resort & SPA

10/10 Excellent

"Always beautiful when I stay here, staff are helpful and every room clean and tidy "

[](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information)

![Hotel Palazzo San niccolò & Spa](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/b8b0f4e2_y.jpg)

### Hotel Palazzo San niccolò & Spa

10/10 Excellent

"One of the best hotels I’ve visited! "

[](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information)

![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg)

### Hotel Borgo di Cortefreda Relais

10/10 Excellent

"The hotel and services exceeded my expectations."

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information)

![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg)

### Hotel Toscana Ambassador

10/10 Excellent

"We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. "

[](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information)

![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg)

### Salvadonica - Borgo del Chianti

10/10 Excellent

"Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again."

[](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information)

![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e_y.jpg)

### Castello Vicchiomaggio

10/10 Excellent

"This beautiful property stole our hearts back in 2019, when my now-wife first visited this magical place. Six years later, we returned — this time to celebrate our wedding reception after tying the knot a few months earlier. From start to finish, everything was beyond wonderful. A special mention to Sandra, the amazing coordinator who made everything run so smoothly, and her fantastic team — Delfina and the lovely lady (whose name, unfortunately, I’ve forgotten) who graciously welcomed and ushered our guests upon arrival. Every detail was handled with care and professionalism. The food and Chianti wines during our celebration were absolutely exceptional — truly a highlight that everyone still talks about! The breakfast and dinner staff were attentive, kind, and ensured everything was perfect throughout our stay. Our rooms were clean, comfortable, and beautifully maintained, with housekeeping doing a fantastic job. We also had the privilege of meeting Mr. John Matta, the owner — such a gracious and inspiring man who leads an extraordinary team. All of our guests loved their stay, and we left with hearts full of joy and gratitude. We can’t wait to come back again — hopefully for our anniversary next time."

[](https://expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information)

![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg)

### Villa Castiglione

10/10 Excellent

"Nice and cute place. Great price. "

[](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information)

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg)

### COMO Castello Del Nero

10/10 Excellent

"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information)

![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg)

### Il Borro - Relais & Châteaux

10/10 Excellent

"A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia"

[](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information)

## Find out more about Chianti Region

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 Chianti Region. 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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- [Duomo hotels](https://expedia.ca/Duomo-Florence-Hotels.0-n6084346-0.Travel-Guide-Filter-Hotels)
- [Hotels in Amalfi Coast](https://expedia.ca/Amalfi-Coast-Hotels.d180060.Travel-Guide-Hotels)
- [Costa Smeralda 5 Star Hotels](https://expedia.ca/5Star-Costa-Smeralda-Hotels.s50-0-d6049197.Travel-Guide-Filter-Hotels)

Flights

- [Cheap Flights from Amalfi Coast](https://expedia.ca/lp/flights/180060/flights-from-amalfi-coast)
- [Cheap Flights to Amalfi Coast](https://expedia.ca/Cheap-Flights-To-Amalfi-Coast.d180060.Travel-Guide-Flights)

Cars

- [Car rentals in Santa Maria Novella](https://expedia.ca/Car-Rentals-In-Santa-Maria-Novella.d6084343.Car-Rental-Guide)
- [Car rentals in Amalfi Coast](https://expedia.ca/Car-Rentals-In-Amalfi-Coast.d180060.Car-Rental-Guide)
- [Car rentals near Port of Livorno](https://expedia.ca/Car-Rentals-In-Port-Of-Livorno.d6190962.Car-Rental-Guide)

Activities

- [Things to do in Amalfi Coast](https://expedia.ca/Things-To-Do-In-Amalfi-Coast.d180060.Travel-Guide-Activities)
- [Things to do in Castiglioncello](https://expedia.ca/Things-To-Do-In-Castiglioncello.d6034140.Travel-Guide-Activities)
- [Things to do in Sorrento Coast](https://expedia.ca/Things-To-Do-In-Sorrento-Coast.d6059422.Travel-Guide-Activities)

Packages

- [Amalfi Coast All-inclusive Vacation Packages](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations/180060/Amalfi-Coast)
- [Capri Island Vacations](https://expedia.ca/Capri-Island.d180062.Destination-Travel-Guides)
- [Terme di Saturnia](https://expedia.ca/Terme-Di-Saturnia-Manciano.d6150383.Vacation-Attraction)
- [Amalfi Coast Vacations](https://expedia.ca/Amalfi-Coast.d180060.Destination-Travel-Guides)
- [Cinque Terre National Park Vacations](https://expedia.ca/Cinque-Terre-National-Park.d180063.Destination-Travel-Guides)

Vacation Rentals

- [Amalfi Coast Vacation Rentals](https://expedia.ca/Amalfi-Coast-Vacation-Rentals.d180060.Travel-Guide-VacationRentals)

General

- [Visit Capri Island](https://expedia.ca/Capri-Island.dx180062)
- [Visit Porto Santo Stefano](https://expedia.ca/Porto-Santo-Stefano.dx6025634)
- [Visit Talamone](https://expedia.ca/Talamone.dx6049866)
- [Visit Santa Maria Novella](https://expedia.ca/Florence-Santa-Maria-Novella.dx6084343)
- [Visit Sorrento Coast](https://expedia.ca/Sorrento-Coast.dx6059422)
- [Visit Elba Island](https://expedia.ca/Elba-Island.dx1090)
- [Visit Palermo Coast](https://expedia.ca/Palermo-Coast.dx6084705)
- [Visit Pisa City Centre](https://expedia.ca/Pisa-Pisa-City-Centre.dx553248633938945235)
- [Visit Brunello di Montalcino Wine Area](https://expedia.ca/Brunello-Di-Montalcino-Wine-Area.dx6342620)
- [Visit Amalfi Coast](https://expedia.ca/Amalfi-Coast.dx180060)

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