Title: Gaiole in Chianti Vacation Rentals from CA $127: 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)

# Gaiole in Chianti Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[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 three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-04-17&endDate=2026-04-19&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

![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/23000000/22750000/22746400/22746331/29a1db75.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)

### Townhouse in Gaiole in Chianti

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

10/10

Exceptional

(12)

"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)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529815/e89534f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529815/d8444557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529815/b77fae70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529815/c8eff036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Gaiole in Chianti

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Rocca-Di-Castagnoli.h2529815.Hotel-Information)

9.2/10

Wonderful

(28)

"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "

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

Shingo

CA $234

CA $271 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Rocca-Di-Castagnoli.h2529815.Hotel-Information)

![Breakfast, lunch, dinner served; Regional cuisine ](https://images.trvl-media.com/lodging/10000000/9410000/9407600/9407590/72c2e838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9410000/9407600/9407590/f6d98a46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Double Room](https://images.trvl-media.com/lodging/10000000/9410000/9407600/9407590/fac53347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/10000000/9410000/9407600/9407590/1f779563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Barberino Tavarnelle

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-La-Locanda-Di-Pietracupa.h9407590.Hotel-Information)

9.4/10

Exceptional

(35)

"Great place, wonderful restaurant"

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

Isabell

CA $209

CA $236 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-La-Locanda-Di-Pietracupa.h9407590.Hotel-Information)

![Birthday party area](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/4b41a72a.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)

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

![Panoramic Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/82a67708.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Siena City Centre

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

9.2/10

Wonderful

(422)

"A great location!"

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

Cheryl

CA $193

CA $218 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/b54f0e1d.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)

![Manicures and pedicures, massages](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/4f19efbc.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)

### Townhouse in Greve in Chianti

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

9.8/10

Exceptional

(71)

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

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

SYDNEY

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

![Deluxe Apartment, City View | Living area](https://images.trvl-media.com/lodging/104000000/103480000/103477000/103476984/35f00952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, City View | Living area](https://images.trvl-media.com/lodging/104000000/103480000/103477000/103476984/21e071ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, City View | Living area](https://images.trvl-media.com/lodging/104000000/103480000/103477000/103476984/24b18dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103480000/103477000/103476984/2ca4e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-Palazzo-Lenzi.h103476984.Hotel-Information)

9.0/10

Wonderful

(2)

"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "

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

Daniel

CA $637

CA $707 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Siena-Hotels-Palazzo-Lenzi.h103476984.Hotel-Information)

![Full-size fridge, oven, stovetop, espresso maker](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/45f2e5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, 1 Bedroom, Non Smoking, Kitchen](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/fb607395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, oven, stovetop, espresso maker](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/48f7d2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/252d70f8.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)

"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

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90770000/90769400/90769387/357afad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90770000/90769400/90769387/6cc36719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/91000000/90770000/90769400/90769387/aead349c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90770000/90769400/90769387/08a6b382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-The-Balcony-Suite-Piazza-Del-Campo-View.h90769387.Hotel-Information)

9.2/10

Wonderful

(16)

"Perfect location to explore Siena, right on the Campo. The apartment was warm and comfortable. As to be expected in such a central location, the noise & music from then restaurants on the piazza was loud till the early hours on Saturday night (so bring earplugs) but the other night was fine. "

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

Nicola

CA $250

CA $287 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Siena-Hotels-The-Balcony-Suite-Piazza-Del-Campo-View.h90769387.Hotel-Information)

![Daily cooked-to-order breakfast (EUR 15 per person)](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/3abf0cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom, Garden View | Private kitchen](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/2a4c017b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Garden View | Room amenity](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/fb99effe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/89200684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Siena

[](https://www.expedia.ca/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

10/10

Exceptional

(42)

"Fantastic place, and I highly recommend it."

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

Hassan

CA $146

CA $168 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

![Panoramic Suite, City View | View from room](https://images.trvl-media.com/lodging/18000000/17470000/17466600/17466559/f1ce4935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/18000000/17470000/17466600/17466559/6e297b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room](https://images.trvl-media.com/lodging/18000000/17470000/17466600/17466559/8f897e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily continental breakfast (EUR 20 per person)](https://images.trvl-media.com/lodging/18000000/17470000/17466600/17466559/301cd527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-Residenza-DEpoca-Palazzo-Borghesi.h17466559.Hotel-Information)

9.6/10

Exceptional

(116)

"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."

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

Linda

CA $247

CA $279 total

includes taxes & fees

Jan 25 - Jan 26, 2026

[](https://www.expedia.ca/Siena-Hotels-Residenza-DEpoca-Palazzo-Borghesi.h17466559.Hotel-Information)

![Royal Apartment | View from room](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/8b57b476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/1808f82b.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)

![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)

### Aparthotel in Sovicille

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

9.2/10

Wonderful

(25)

"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 $105

CA $136 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![TV](https://images.trvl-media.com/lodging/74000000/73250000/73243100/73243015/3b89348d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73250000/73243100/73243015/1e456e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Apartment](https://images.trvl-media.com/lodging/74000000/73250000/73243100/73243015/7d8d1a70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73250000/73243100/73243015/d0152fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-Astonish-Cathedral-View.h73243015.Hotel-Information)

10/10

Exceptional

(1)

[](https://www.expedia.ca/Siena-Hotels-Astonish-Cathedral-View.h73243015.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/a35e59bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment | Living area](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/824253fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/babe056b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/b14849f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Asciano

[](https://www.expedia.ca/Asciano-Hotels-Albergo-Diffuso-Borgo-Santo.h96934275.Hotel-Information)

CA $354

CA $398 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Asciano-Hotels-Albergo-Diffuso-Borgo-Santo.h96934275.Hotel-Information)

![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/3000000/2730000/2723600/2723529/169b7345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/37f63acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/a7b1b268.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)

"Great people, great location great service"

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

James

CA $179

CA $204 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/aa257512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Land view from property](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/123a3a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/e87f673d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Suite, 1 Bedroom | Bathroom](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/a629bdd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Residenzia-Del-Sogno.h25163522.Hotel-Information)

9.8/10

Exceptional

(14)

"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "

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

Katherine

CA $209

CA $237 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Residenzia-Del-Sogno.h25163522.Hotel-Information)

![Deluxe Apartment | Living area](https://images.trvl-media.com/lodging/104000000/103150000/103143500/103143444/a951c070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio | Living area](https://images.trvl-media.com/lodging/104000000/103150000/103143500/103143444/ab1960d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment | Living area](https://images.trvl-media.com/lodging/104000000/103150000/103143500/103143444/4c70176f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment](https://images.trvl-media.com/lodging/104000000/103150000/103143500/103143444/c21ed8ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-Casa-Ciseri.h103143444.Hotel-Information)

9.8/10

Exceptional

(9)

"Very nice stay!"

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

Danielle

CA $362

CA $404 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Siena-Hotels-Casa-Ciseri.h103143444.Hotel-Information)

![Superior Double Room, 1 Queen Bed, Private Bathroom, City View | View from room](https://images.trvl-media.com/lodging/30000000/29350000/29346600/29346534/435b8942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room, 1 Queen Bed, Private Bathroom, City View](https://images.trvl-media.com/lodging/30000000/29350000/29346600/29346534/9a309ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room, 1 Queen Bed, Private Bathroom, City View | Room amenity](https://images.trvl-media.com/lodging/30000000/29350000/29346600/29346534/711504d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room, 1 Queen Bed, Private Bathroom, City View | View from room](https://images.trvl-media.com/lodging/30000000/29350000/29346600/29346534/e840c9c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-BB-Palazzo-Del-Magnifico.h29346534.Hotel-Information)

9.8/10

Exceptional

(63)

"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "

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

Rodolfo

[](https://www.expedia.ca/Siena-Hotels-BB-Palazzo-Del-Magnifico.h29346534.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31790000/31785900/31785878/41ce111e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room | Living area](https://images.trvl-media.com/lodging/32000000/31790000/31785900/31785878/2151e70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/32000000/31790000/31785900/31785878/f1746d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/32000000/31790000/31785900/31785878/1fe084e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Siena City Centre

[](https://www.expedia.ca/Siena-Hotels-Palazzo-Del-Papa-BB.h31785878.Hotel-Information)

9.6/10

Exceptional

(96)

"Hamza was so wonderful and accommodating, would definitely stay here again!"

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

Elise

CA $253

CA $285 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Siena-Hotels-Palazzo-Del-Papa-BB.h31785878.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/3000000/2530000/2528600/2528599/c8735d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily continental breakfast (EUR 8.50 per person)](https://images.trvl-media.com/lodging/3000000/2530000/2528600/2528599/27db4a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/3000000/2530000/2528600/2528599/0334e3a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2530000/2528600/2528599/42b1a40e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Gimignano City Centre

[](https://www.expedia.ca/San-Gimignano-Hotels-Palazzo-Al-Torrione-2.h2528599.Hotel-Information)

9.2/10

Wonderful

(107)

"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "

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

Angel

CA $130

CA $191 total

includes taxes & fees

Jan 19 - Jan 20, 2026

[](https://www.expedia.ca/San-Gimignano-Hotels-Palazzo-Al-Torrione-2.h2528599.Hotel-Information)

![Dining room](https://images.trvl-media.com/lodging/104000000/103180000/103175000/103174974/43e34d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/104000000/103180000/103175000/103174974/ab25a144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103180000/103175000/103174974/776fd0fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/104000000/103180000/103175000/103174974/092be31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Siena Historical Center

[](https://www.expedia.ca/Siena-Hotels-Villa-Liberty-TownHouse.h103174974.Hotel-Information)

10/10

Exceptional

(4)

"Amazing place in a perfect location. "

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

Ben

CA $548

CA $608 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Siena-Hotels-Villa-Liberty-TownHouse.h103174974.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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## Top Gaiole in Chianti Hotel Reviews

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

###  Palazzo Ravizza

10/10 Excellent

"Having booked with another local hotel - The Athena - who were completely obnoxious and unhelpful regarding the parking. I stumbled across this gem. The staff were so helpful and accomplished \~ first class customer service."

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

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

### Hotel Athena

10/10 Excellent

"Great location, very friendly staff"

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

![Hotel Mulino di Firenze, WorldHotels Crafted](https://images.trvl-media.com/lodging/4000000/3620000/3620000/3619961/e8804f70_y.jpg)

### Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"This hotel was one of the best we have ever stayed in. Despite our early arrival, the staff was able to accommodate us with a room right away. While we waited, we explored the property and were immediately impressed by the stunning views. Our bags were delivered to our room for us, allowing us to fully enjoy our time on the grounds. The staff was exceptionally helpful, and the housekeeping team did an outstanding job keeping our room spotless and ensuring our refrigerator was always stocked with water. Overall, the property offered breathtaking views, excellent cleanliness, and warm, friendly service. We loved every bit of it 10/10 recommend! "

[](https://expedia.ca/Florence-Hotels-Mulino-Di-Firenze.h3619961.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)

![Hotel Borgo San Luigi](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/69a3ac66_y.jpg)

### Hotel Borgo San Luigi

10/10 Excellent

"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "

[](https://expedia.ca/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.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 Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg)

### Hotel Chiusarelli

10/10 Excellent

"The room was very clean and the bathroom was nice. The staff was very helpful especially because we had personal issues to deal with and places we had to get to for resolution. They helped us navigate several things that we could not have done on our own. We are grateful! "

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

"The Grand Hotel Continental in Siena is a rare gem,elegant, inviting, and steeped in history. From the beautifully preserved interiors to the warm, attentive staff, every detail makes you feel genuinely cared for. Its central location is unbeatable, placing Siena’s most charming sights just steps away. A perfect blend of luxury and authentic Tuscan character, this hotel transforms a stay in Siena into something truly unforgettable. The foods were yummy took! "

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

"Great place I love it"

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