Title: Gaiole in Chianti Vacation Rentals from $60: Search Short-Term Rentals | Expedia.com

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

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=603149&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/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 three months

[Jun 19 - Jun 21](https://www.expedia.com/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)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=603149&startDate=2026-07-17&endDate=2026-07-19&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

![Interior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/f910598d.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)

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

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/04a72517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gaiole in Chianti

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

$632 nightly

$637 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/ce6a104a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Suite | Frette Italian sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/c33da520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/73ef5376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, facials, massages](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/4c8f3824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Gaiole in Chianti

[](https://www.expedia.com/Gaiole-In-Chianti-Hotels-La-Pieve-Marsina.h6029534.Hotel-Information)

9.8/10

Exceptional

(22 reviews)

"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "

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

Massimo

$217 nightly

$248 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Gaiole-In-Chianti-Hotels-La-Pieve-Marsina.h6029534.Hotel-Information)

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

![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)

![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)

### Townhouse in Gaiole in Chianti

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

10/10

Exceptional

(13 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.com/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/81953563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/0e2eec35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/a822b4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/656217ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Gaiole in Chianti

[](https://www.expedia.com/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

10/10

Exceptional

(8 reviews)

"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "

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

Ravin N.

$1,023 nightly

$1,028 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.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)

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

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946075/5491f8f6.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)

### Apartment in Gaiole in chianti

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

$353 nightly

$357 total

Mar 28 - Mar 29

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/afb73a16.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)

### Villa in Gaiole in Chianti

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

$7,406 nightly

$7,406 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946071/a0d1343a.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)

### Apartment in Gaiole in chianti

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

$268 nightly

$273 total

Mar 27 - Mar 28

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946065/c9e0e441.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)

![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99946100/99946065/ed82dd6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Gaiole in chianti

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

$480 nightly

$484 total

Mar 26 - Mar 27

Total with taxes and fees

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

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

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

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

### Townhouse in Loro Ciuffenna

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

9.4/10

Exceptional

(23 reviews)

"The staff were great and the villa was amazing"

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

Ralphvincent

$160 nightly

$176 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Classic Double Room, 1 Double Bed | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/c7b333e5.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)

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

### Townhouse in Sovicille

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

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

$97 nightly

$110 total

Mar 26 - Mar 27

Total with taxes and fees

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

![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)

![Superior Room (Camera 2) | Premium bedding, down comforters, individually furnished, desk](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/38f4bf63.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/c755ff2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Castelnuovo Berardenga

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

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

$169 nightly

$186 total

Apr 16 - Apr 17

Total with taxes and fees

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

![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)

![Villa | Living area | 24-inch flat-screen TV with satellite channels, DVD player](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/58622732.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)

### Condo resort in Trequanda

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

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

![Villa, Air conditioning, Courtyard View | Exterior](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/6b3321e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/6427b5b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/fee64891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, Air conditioning, Courtyard View | Property grounds](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/1f2094c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Monteriggioni

[](https://www.expedia.com/Monteriggioni-Hotels-Villa-Montecastello.h126444856.Hotel-Information)

$170 nightly

$191 total

Apr 3 - Apr 4

Total with taxes and fees

[](https://www.expedia.com/Monteriggioni-Hotels-Villa-Montecastello.h126444856.Hotel-Information)

![La casa di Jakin | Terrace/patio](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/48f6b5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![La casa di Donna Lisa | View from room](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/f5ed0303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![La casa di Bohaz | View from room](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/630eb39a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![La casa dell'Architetto | Living area | 43-inch flat-screen TV with digital channels](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/0f87b43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Casole d'Elsa

[](https://www.expedia.com/Casole-DElsa-Hotels-Tenuta-Cantona.h100139702.Hotel-Information)

$170 nightly

$190 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Casole-DElsa-Hotels-Tenuta-Cantona.h100139702.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)

![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)

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

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

### Townhouse in San Casciano in Val di Pesa

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

9.6/10

Exceptional

(100 reviews)

"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "

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

rose

$162 nightly

$183 total

Mar 24 - Mar 25

Total with taxes and fees

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

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

### Residence in Monte San Savino

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

9.2/10

Wonderful

(40 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.com/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/126000000/125630000/125624500/125624410/6a704d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/126000000/125630000/125624500/125624410/f9d2ee9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/126000000/125630000/125624500/125624410/53f99d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, wheelchair access](https://images.trvl-media.com/lodging/126000000/125630000/125624500/125624410/b7016f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Reggello

[](https://www.expedia.com/Reggello-Hotels-LE-BOTTI-FIORENTINE.h125624410.Hotel-Information)

$141 nightly

$161 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Reggello-Hotels-LE-BOTTI-FIORENTINE.h125624410.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/8dbfb990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/c7f9cf0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/fbb1db35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/236bbc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Asciano

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

$224 nightly

$253 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Food court](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/cb376ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/97797fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (for 2 - 4 People) | 1 bedroom, hypo-allergenic bedding, down comforters, Select Comfort beds](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/53451d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, 1 Bedroom, Terrace | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/ccba610a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Monteriggioni

[](https://www.expedia.com/Monteriggioni-Hotels-Antico-Borgo-Poggiarello.h3620800.Hotel-Information)

9.0/10

Wonderful

(20 reviews)

"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "

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

James Bakley

$256 nightly

$285 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Monteriggioni-Hotels-Antico-Borgo-Poggiarello.h3620800.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)

![Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, individually decorated](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/0c1e54bd.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)

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

### Townhouse in Greve in Chianti

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

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

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

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-06&endDate=2026-04-07&regionId=603149&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VILLA)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APART_HOTEL)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=RESIDENCE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Gaiole+in+Chianti%2C+Tuscany%2C+Italy&regionId=603149&latLong=43.467532%2C11.43409&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CHALET)

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## Top Gaiole in Chianti Hotel Reviews

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/f43eb5fd_y.jpg)

### Hotel Chiusarelli

8/10 Good

"The hotel was just outside of the town, so the location was good. It was a beautiful property. The breakfast was good. Just be prepared to walk stairs. No lifts. But overall, good. "

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

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/5eddd92b_y.jpg)

###  Palazzo Ravizza

10/10 Excellent

"This is a gem and well worth the stay!!! So so amazing"

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

![Hu Firenze Camping In Town](https://images.trvl-media.com/lodging/19000000/18340000/18331800/18331768/03b78683_y.jpg)

### Hu Firenze Camping In Town

10/10 Excellent

"Fantastic accommodations in Florence. Easy drive from any part of the city, also a 1-minute walk to the bus if you don't have your own car or just don't feel like driving. Would definitely stay here again, highly recommend!"

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

![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/e3da527a_y.jpg)

### Hotel Italia

10/10 Excellent

"Very close to the bus and train station, lovely staff, clean room but a bit too warm even in February and no water kettle in the room, which was a bit surprising. "

[](https://expedia.com/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information)

![Radisson Blu Hotel, Florence](https://images.trvl-media.com/lodging/1000000/20000/14500/14476/efa5cbd4_y.jpg)

### Radisson Blu Hotel, Florence

10/10 Excellent

"The hotel was great, just the location was a little difficult to get in."

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

![La Certosa di Pontignano](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/8b3eb5da_y.jpg)

### La Certosa di Pontignano

6/10 Okay

"Here is a polished version of your review with improved grammar and structure, keeping your message clear and balanced: --- Great and beautiful place. The food is also very good, and the overall atmosphere is charming. However, the bed was terrible. The mattress was old, and the springs made it very uncomfortable, so I couldn’t sleep well. I’ve stayed in many different hotels and have never experienced such a bad bed. I understand that the concept and vibe of the place are meant to feel historic or classic, but for a property of this level, the bed should match the quality of the rest of the experience. Upgrading the mattresses would make a big difference."

[](https://expedia.com/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information)

![Italiana Hotels Florence](https://images.trvl-media.com/lodging/1000000/10000/7700/7698/e1967d06_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.com/Florence-Hotels-Italiana-Hotels-Florence.h7698.Hotel-Information)

![Four Points by Sheraton Siena](https://images.trvl-media.com/lodging/1000000/860000/852400/852305/e65a78e2_y.jpg)

### Four Points by Sheraton Siena

6/10 Okay

"The air conditioning was bad. I was perspiring during my bed time. Other things were ok. Ample parking. "

[](https://expedia.com/Siena-Hotels-Four-Points-By-Sheraton-Siena.h852305.Hotel-Information)

![Agriturismo San Sano](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/6322c664_y.jpg)

### Agriturismo San Sano

10/10 Excellent

"You can never go wrong in Toscana , even in off season . San Sano even more so, hidden from mass tourism. "

[](https://expedia.com/Gaiole-In-Chianti-Hotels-Hotel-Residence-San-Sano.h1491964.Hotel-Information)

## Find out more about Gaiole in Chianti

**Everything you need to know about Gaiole in Chianti vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaiole in Chianti vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Gaiole in Chianti vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Gaiole in Chianti. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gaiole in Chianti in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $60 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Gaiole in Chianti rentals**

At Expedia, we put the best Gaiole in Chianti vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gaiole in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaiole in Chianti vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaiole in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Apartments in Gaiole in Chianti ](https://expedia.com/Gaiole-In-Chianti-Apartments.d603149-aaApartments.Travel-Guide-Accommodation)
- [Villas in Gaiole in Chianti ](https://expedia.com/Gaiole-In-Chianti-Villas.d603149-aaVillas.Travel-Guide-Accommodation)
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- [B&B in Gaiole in Chianti ](https://expedia.com/Gaiole-In-Chianti-Bed-And-Breakfast.d603149-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Town Houses in Gaiole in Chianti ](https://expedia.com/Gaiole-In-Chianti-Town-Houses.d603149-aaTownHouses.Travel-Guide-Accommodation)
- [Lodges in Gaiole in Chianti ](https://expedia.com/Gaiole-In-Chianti-Lodges.d603149-aaLodges.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Gaiole in Chianti?

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### How many vacation rentals are there in Gaiole in Chianti?

### What’s there to see and do in Gaiole in Chianti?

### What’s a vacation rental in Gaiole in Chianti like?

### Expedia's Latest Trends

Hotels

- [Hotels in Florence](https://expedia.com/Florence-Hotels.d1222.Travel-Guide-Hotels)
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Flights

- [Cheap Flights to Pisa](https://expedia.com/Cheap-Flights-To-Pisa.d2877.Travel-Guide-Flights)
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Packages

- [Florence Vacation](https://expedia.com/Florence.d1222.Destination-Travel-Guides)

Vacation Rentals

- [Florence Vacation Rentals](https://expedia.com/Florence-Vacation-Rentals.d1222.Travel-Guide-VacationRentals)

General

- [Visit Follonica](https://expedia.com/Follonica.dx6123914)
- [Visit San Gimignano](https://expedia.com/San-Gimignano.dx11091)
- [Visit Florence](https://expedia.com/Florence.dx1222)
- [Visit Viareggio](https://expedia.com/Viareggio.dx4894)
- [Visit Portoferraio](https://expedia.com/Portoferraio.dx4876)
- [Visit Monte Argentario](https://expedia.com/Monte-Argentario.dx602888)
- [Visit Siena](https://expedia.com/Siena.dx9821)

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