Title: Gaiole in Chianti Vacation Rentals from CA $95: Short-Term Rentals for 2026 | Expedia.ca

[Gaiole in Chianti Travel Guide](https://expedia.ca/Gaiole-In-Chianti.dx603149)[Hotels in Gaiole in Chianti](https://expedia.ca/Gaiole-In-Chianti-Hotels.d603149.Travel-Guide-Hotels)[Flights to Gaiole in Chianti](https://expedia.ca/Cheap-Flights-To-Gaiole-In-Chianti.d603149.Travel-Guide-Flights)[Things to do in Gaiole in Chianti](https://expedia.ca/Things-To-Do-In-Gaiole-In-Chianti.d603149.Travel-Guide-Activities)[Gaiole in Chianti Car Rentals](https://expedia.ca/Car-Rentals-In-Gaiole-In-Chianti.d603149.Car-Rental-Guide)[Gaiole in Chianti Vacation Packages](https://expedia.ca/Gaiole-In-Chianti.d603149.Destination-Travel-Guides)

![View over the hills from the Brolio Castle](https://images.trvl-media.com/place/603149/c6d3b602-5ecb-46fa-8174-b38eecda296b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/603149/c6d3b602-5ecb-46fa-8174-b38eecda296b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Gaiole in Chianti vacation rentals

![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)

![Interior](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/aba3f4d4.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)

### L' Eroico

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

Gaiole in Chianti

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)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/eab05df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/4366b9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Concierge desk](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/bdf789e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Double Room, 1 Double Bed](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/c7b333e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa di Campagna in Toscana

[](https://www.expedia.ca/Sovicille-Hotels-Casa-Di-Campagna-In-Toscana.h12642590.Hotel-Information)

Sovicille

9.4/10

Exceptional

(21 reviews)

"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"

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

Alasdair

CA $107

CA $123 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Sovicille-Hotels-Casa-Di-Campagna-In-Toscana.h12642590.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)

![Birthday party area](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/498c2bc0.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)

### Terre di Baccio

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

Greve in Chianti

9.8/10

Exceptional

(72 reviews)

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

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

SYDNEY

CA $445

CA $496 total

includes taxes & fees

Feb 28 - Mar 1

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

![Memory foam beds, minibar, individually decorated](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/e7f84930.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)

### Villa il Fedino

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

San Casciano in Val di Pesa

9.6/10

Exceptional

(99 reviews)

"Great people, great location great service"

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

James

CA $182

CA $207 total

includes taxes & fees

Feb 26 - Feb 27

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

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/f0bca152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa | Living area](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/58622732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/65f08668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/08c45c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury resort in the Tuscan countryside

[](https://www.expedia.ca/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

Trequanda

[](https://www.expedia.ca/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e04fd69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/4f173bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/100f6cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Triple Room | Bathroom](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c721d6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artisti del Cavallo Tourism

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

Foiano della Chiana

8.4/10

Very good

(24 reviews)

"Good house for one night. "

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

Heiner

CA $114

CA $129 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/190e02d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/b53ae9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/a47cb16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/64c8d4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Pozzo di Sant'Andrea

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

Siena

9.8/10

Exceptional

(16 reviews)

"Great host, lovely place near Siena"

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

Prem

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/782fdb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/8b91ef4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/dc2ef8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms, Garden View (Maria) | Living room](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/667a06a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Borgo Lucignanello Bandini

[](https://www.expedia.ca/Montalcino-Hotels-Borgo-Lucignanello-Bandini.h11031336.Hotel-Information)

Montalcino

9.4/10

Exceptional

(12 reviews)

"Beautiful stay "

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

Marc

CA $446

CA $504 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Montalcino-Hotels-Borgo-Lucignanello-Bandini.h11031336.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)

![Aerial view](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/b614c935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chianti Village Morrocco

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

Barberino Tavarnelle

8.6/10

Excellent

(112 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)

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

![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/6055a736.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)

![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)

### Villa Cassia di Baccano

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

Loro Ciuffenna

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 $219

CA $241 total

includes taxes & fees

Mar 10 - Mar 11

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

![Room amenity](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/3d8bc861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/a8002544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/6ca01702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/a6e9d423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Siena Vip

[](https://www.expedia.ca/Siena-Hotels-Siena-Vip.h16245550.Hotel-Information)

Siena City Centre

9.2/10

Wonderful

(427 reviews)

"Nice place!"

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

Pavel

CA $133

CA $153 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Siena-Hotels-Siena-Vip.h16245550.Hotel-Information)

![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/258f72ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room (Camera 2)](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/38f4bf63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Condo (Casa Palei B)](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/c8b78159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/920701e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa di Sotto

[](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Villa-Di-Sotto.h2432264.Hotel-Information)

Castelnuovo Berardenga

9.4/10

Exceptional

(28 reviews)

"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."

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

Amelia

CA $214

CA $236 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Villa-Di-Sotto.h2432264.Hotel-Information)

![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/98406b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/521d6cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/a8ce016d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/13e470bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello di Gargonza

[](https://www.expedia.ca/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

Monte San Savino

9.2/10

Wonderful

(39 reviews)

"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."

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

David

[](https://www.expedia.ca/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/21000000/20150000/20140700/20140609/d72b3a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/21000000/20150000/20140700/20140609/7785950f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/21000000/20150000/20140700/20140609/5a73c489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, free toiletries, hair dryer, bidet](https://images.trvl-media.com/lodging/21000000/20150000/20140700/20140609/66079b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Domus il Palio B&B

[](https://www.expedia.ca/Siena-Hotels-Domus-Il-Palio-BB.h20140609.Hotel-Information)

Ravacciano

9.2/10

Wonderful

(83 reviews)

"Hotel clean comfortable. No elevator, no reception desk. "

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

Karin

[](https://www.expedia.ca/Siena-Hotels-Domus-Il-Palio-BB.h20140609.Hotel-Information)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/7fe98579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/53d9424a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/65f6d95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/971773cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tuscasì Aparthotel

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

Sovicille

9.0/10

Wonderful

(26 reviews)

"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "

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

Sergey

CA $83

CA $112 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

![Breakfast meal](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218707/da164cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218707/a07ebcd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218707/fe380723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218707/95016d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### B&B Il Corso

[](https://www.expedia.ca/Siena-Hotels-BB-Il-Corso.h5218707.Hotel-Information)

Siena City Centre

9.8/10

Exceptional

(193 reviews)

"Great location"

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

Mina

[](https://www.expedia.ca/Siena-Hotels-BB-Il-Corso.h5218707.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/7fc2c578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/c32d3de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/593e3ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/16000000/15440000/15434500/15434499/29beacc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa La Ginestra

[](https://www.expedia.ca/Subbiano-Hotels-Villa-La-Ginestra.h15434499.Hotel-Information)

Subbiano

9.6/10

Exceptional

(5 reviews)

"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."

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

Philippe

[](https://www.expedia.ca/Subbiano-Hotels-Villa-La-Ginestra.h15434499.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/12ea27d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room, City View](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/f7c15fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/96a7251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/c5858744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Casa di Ines

[](https://www.expedia.ca/San-Gimignano-Hotels-La-Casa-Di-Ines.h117149866.Hotel-Information)

San Gimignano City Centre

9.6/10

Exceptional

(8 reviews)

"Love this town. Location is great "

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

William

CA $119

CA $139 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/San-Gimignano-Hotels-La-Casa-Di-Ines.h117149866.Hotel-Information)

![Double Room (Ginevra) | View from room](https://images.trvl-media.com/lodging/25000000/24360000/24356400/24356387/d4389b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room (Cristiana) | Room amenity](https://images.trvl-media.com/lodging/25000000/24360000/24356400/24356387/3d154b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room (Cristiana) | Room amenity](https://images.trvl-media.com/lodging/25000000/24360000/24356400/24356387/7c687ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Duplex (Claudio)](https://images.trvl-media.com/lodging/25000000/24360000/24356400/24356387/f074c01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Casa Mastacchi

[](https://www.expedia.ca/Siena-Hotels-A-Casa-Mastacchi.h24356387.Hotel-Information)

Siena City Centre

7.8/10

Good

(25 reviews)

"Pleasant place"

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

Claude

CA $139

CA $160 total

includes taxes & fees

Mar 22 - Mar 23

[](https://www.expedia.ca/Siena-Hotels-A-Casa-Mastacchi.h24356387.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/39997d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/4e7093c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/a67674df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/4734ab61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Vacanze Le Case

[](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.Hotel-Information)

San Gimignano

9.0/10

Wonderful

(8 reviews)

"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10\. "

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

Jackie

CA $150

CA $174 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.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.

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## Find vacation rentals that suit your style

Aparthotels

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Villas

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Apartments

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Private vacation homes

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Residences

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE)

Condos

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Chalets

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## Top Gaiole in Chianti Hotel Reviews

![Borgo Grondaie](https://images.trvl-media.com/lodging/1000000/910000/905800/905710/58e23d32_y.jpg)

### Borgo Grondaie

10/10 Excellent

"Wonderful service, wonderful accomodation, wonderful breakfast. Wonderful "

[](https://expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information)

![Hu Firenze Camping In Town](https://images.trvl-media.com/lodging/19000000/18340000/18331800/18331768/6194b9bd_y.jpg)

### Hu Firenze Camping In Town

10/10 Excellent

"Staff was extremely helpful and friendly. The chalet room was clean, warm and comfortable. Bus stop right outside made it very convenient to travel to city center "

[](https://expedia.ca/Florence-Hotels-Firenze-Camping-In-Town.h18331768.Hotel-Information)

![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg)

### Hotel Athena

10/10 Excellent

"Estupenda estadia, el cuarto estaba muy comodo y limpio, nos proporcionaron agua y cafe, el staff muuuy amable, el hotel tiene unas vistas espectaculares y el desayuno buffet, delicioso, ademas de estar en una muy buena ubicacion para recorrer siena sin preocupacion, definitivamente volveria a hospedarme aqui"

[](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information)

![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg)

### Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Exceptional hospitality. "

[](https://expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.Hotel-Information)

![Italiana Hotels Florence](https://images.trvl-media.com/lodging/1000000/10000/7700/7698/ab697e78_y.jpg)

### Italiana Hotels Florence

10/10 Excellent

"Italiana Hotels Florence was a very enjoyable place to stay. The hotel was comfortable, clean, and well organized, making our visit to Florence relaxing and smooth. The included breakfast was a great bonus and made our mornings easy and convenient. We also appreciated the free parking, which was very helpful and practical. The staff were great, friendly, professional, and always ready to assist. Overall, a wonderful experience and a solid choice for anyone visiting Florence."

[](https://expedia.ca/Florence-Hotels-Italiana-Hotels-Florence.h7698.Hotel-Information)

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg)

### Hotel Chiusarelli

10/10 Excellent

"Perfect location … great quality/value … nice staff"

[](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information)

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg)

###  Palazzo Ravizza

10/10 Excellent

"Excellent location, very clear instructions to get into the city for those coming in by car, a warm welcome by the staff, a super comfy bed and a great breakfast, what more could we ask for! All in all a great stay at the Palazzo."

[](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information)

![Radisson Blu Hotel, Florence](https://images.trvl-media.com/lodging/1000000/20000/14500/14476/91a79091_y.jpg)

### Radisson Blu Hotel, Florence

10/10 Excellent

"Lovely brand new hotel couldn’t fault a thing - easy to get to from the main motorways arrived very late Friday early hours sat morning the chap on reception was super nice and very friendly . Swimming pool outside will be lovely in the summer to cold in January . Recommend this hotel ."

[](https://expedia.ca/Florence-Hotels-Conference-Florentia-Hotel.h14476.Hotel-Information)

![Villa Olmi Firenze](https://images.trvl-media.com/lodging/2000000/1450000/1441600/1441538/09965ee7_y.jpg)

### Villa Olmi Firenze

10/10 Excellent

"Very charming, clean and fresh"

[](https://expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Olmi-Firenze.h1441538.Hotel-Information)

## Find out more about Gaiole in Chianti

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 Gaiole in Chianti. 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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## Frequently asked questions

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