Title: Gaiole in Chianti Vacation Rentals from CA $84: 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

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=603149&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 two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-05-29&endDate=2026-05-31&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)

![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)

![Aerial view](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/ddbdc210.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)

![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/dcfa042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/52aa6660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/782eb623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/25aedd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

Gaiole in Chianti

CA $9,613

CA $10,421 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946071/788ed790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946071/9e853efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946071/a0d1343a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946071/35c8ff9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Apartment-Reggioli-Appartamento-Erborista-With-Mountain-View.h99946071.Hotel-Information)

Gaiole in chianti

CA $337

CA $343 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Apartment-Reggioli-Appartamento-Erborista-With-Mountain-View.h99946071.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/f910598d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/a7d5ba95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/1858bc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/b68fa7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.Hotel-Information)

Gaiole in Chianti

CA $745

CA $889 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946075/eb574019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946075/b51b3e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946075/a36e821c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946075/edf062df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Apartment-Reggioli-Appartamento-Falegname-With-Mountain-View.h99946075.Hotel-Information)

Gaiole in chianti

CA $399

CA $405 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Apartment-Reggioli-Appartamento-Falegname-With-Mountain-View.h99946075.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946065/fac4cbee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946065/d9b8b48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946065/fde0af7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946065/c9e0e441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Apartment-Reggioli-Appartamento-Del-Cestaio-With-Mountain-View.h99946065.Hotel-Information)

Gaiole in chianti

CA $567

CA $574 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Apartment-Reggioli-Appartamento-Del-Cestaio-With-Mountain-View.h99946065.Hotel-Information)

![Breakfast, lunch, dinner served; Regional cuisine ](https://images.trvl-media.com/lodging/19000000/18340000/18331800/18331768/03b78683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 12 per person)](https://images.trvl-media.com/lodging/19000000/18340000/18331800/18331768/367eddaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18340000/18331800/18331768/9828459b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Tent (Urban Safari) | Balcony view](https://images.trvl-media.com/lodging/19000000/18340000/18331800/18331768/8f7a9aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hu Firenze Camping In Town

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

Florence

8.8/10

Excellent

(1,618 reviews)

"It was a grt place to stay"

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

Sunitha

CA $66

CA $84 total

includes taxes & fees

Feb 22 - Feb 23

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

![Deluxe Apartment | Living area](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/fba76c40.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)

![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

(426 reviews)

"Nice place!"

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

Pavel

CA $137

CA $157 total

includes taxes & fees

Feb 9 - Feb 10

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

![Balcony](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218707/fe380723.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)

![Reception](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218707/7aa0755c.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

(192 reviews)

"Safe, clean, close to all attractions"

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

Carlo

CA $124

CA $143 total

includes taxes & fees

Feb 9 - Feb 10

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

![Property entrance](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/f7bc825c.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 2 - Mar 3

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

![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)

![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)

### 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)

![Property grounds](https://images.trvl-media.com/lodging/21000000/20150000/20140700/20140609/d72b3a9a.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)

![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)

![](https://images.trvl-media.com/lodging/21000000/20150000/20140700/20140609/7785950f.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

(82 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)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/eab05df6.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)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/d37077fb.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)

### Casa di Campagna in Toscana

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

Sovicille

9.4/10

Exceptional

(20 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

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

![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/46c3ab32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/7dd80bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/946f4e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/f58a3308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bosco della Spina

[](https://www.expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

Murlo

9.6/10

Exceptional

(169 reviews)

"Views are amazing. Staff are very pleasant and helpful. "

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

Maureen

CA $93

CA $116 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

![Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5467h3644x6y6-bfae763b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/81c3f8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5470h3644x0y0-9c1f6ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/543e1f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DormiVeglia B&B

[](https://www.expedia.ca/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information)

Monte San Savino

10/10

Exceptional

(27 reviews)

"Amazing, warm, sweet, lovely, such a gem of a place!"

![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg)

Melissa Hyun Joo

[](https://www.expedia.ca/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.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)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.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)

![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.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

Feb 15 - Feb 16

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

![Exterior](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/c3f2502a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double or Twin Room, 1 Bedroom](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/41636195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/30d81c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24380000/24373100/24373081/b87c70b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### THE MONNA LISA RESORT

[](https://www.expedia.ca/Arezzo-Hotels-La-Valle-Di-Monna-Lisa.h24373081.Hotel-Information)

Arezzo

9.2/10

Wonderful

(9 reviews)

"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "

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

Bart

[](https://www.expedia.ca/Arezzo-Hotels-La-Valle-Di-Monna-Lisa.h24373081.Hotel-Information)

![Tasting room](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/bc901666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 1 Double Bed](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/23aa0514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view from property](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/391cb1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Concierge desk](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/163ec176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Battistero Siena - Residenza d'Epoca

[](https://www.expedia.ca/Siena-Hotels-Il-Battistero-Siena-Residenza-DEpoca.h10536156.Hotel-Information)

Siena City Centre

9.6/10

Exceptional

(196 reviews)

"Great location and friendly staff. "

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

Parissa

[](https://www.expedia.ca/Siena-Hotels-Il-Battistero-Siena-Residenza-DEpoca.h10536156.Hotel-Information)

![Standard Double Room | Bathroom](https://images.trvl-media.com/lodging/4000000/3410000/3405200/3405195/9ea547ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room](https://images.trvl-media.com/lodging/4000000/3410000/3405200/3405195/0c6247e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room | Living area](https://images.trvl-media.com/lodging/4000000/3410000/3405200/3405195/531aecc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/4000000/3410000/3405200/3405195/414d06dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Piazza Paradiso Accomodation

[](https://www.expedia.ca/Siena-Hotels-Piazza-Paradiso-Accomodation.h3405195.Hotel-Information)

Siena City Centre

9.2/10

Wonderful

(155 reviews)

"What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza del Campo. Looking forward to staying with Piazza Paradiso accommodation again. We will definitely recommend Piazza Paradiso to all our friends visiting Siena!"

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

Niels G.

[](https://www.expedia.ca/Siena-Hotels-Piazza-Paradiso-Accomodation.h3405195.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/17000000/16260000/16252900/16252824/fecfe7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk](https://images.trvl-media.com/lodging/17000000/16260000/16252900/16252824/9166ea67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/17000000/16260000/16252900/16252824/a807b36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/17000000/16260000/16252900/16252824/62fccb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### B&B Dei Rossi

[](https://www.expedia.ca/Siena-Hotels-BB-Dei-Rossi.h16252824.Hotel-Information)

Siena City Centre

8.2/10

Very good

(18 reviews)

"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "

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

Alana

CA $103

CA $120 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Siena-Hotels-BB-Dei-Rossi.h16252824.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

Villas

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Private vacation homes

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Aparthotels

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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=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE)

Condos

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Chalets

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## Top Gaiole in Chianti Hotel Reviews

![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)

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

### Hotel Athena

10/10 Excellent

"Great hotel, beautiful view and excellent service from the personnel. "

[](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

"Room, bathroom and breakfast were wonderful. WiFi was not great. Lovely location and pretty property. "

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

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

### Italiana Hotels Florence

10/10 Excellent

"Clean room with nice staffs on site and at the restaurant "

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

![La Certosa di Pontignano](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7_y.jpg)

### La Certosa di Pontignano

10/10 Excellent

"Remarkable historic monastery well maintained in an extraordinary location. Food: superb Tuscan cuisine."

[](https://expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.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

"What a fun way to stay! Glamping tent is very clean, roomy, and in like-new condition. Maybe a bit cold for winter, but has heating. The tent material makes vibrations on a windy night. Has supermarket within campus (good price!) but closes early at 8pm. Restaurant/bar is exceptional. Front desk staff very helpful and friendly. Bus route 14 to central Florence is immediately outside the gate, takes 30+ minutes, and is seldom on schedule. Otherwise, walk 10 minutes to nearby train station and take 10 minutes train to Florence station."

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