Title: Chianti Region Vacation Rentals from $52: Search Short-Term Rentals | Expedia.com

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

![Chianti Region which includes farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=603148&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 two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chianti Region vacation rentals

![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)

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

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

![Studio, 1 Double Bed (2 adults) | Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/9d79efbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Barberino Tavarnelle

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

8.6/10

Excellent

(112 reviews)

"Front desk was very helpful and very comfortable room. "

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

Chris

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

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

![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)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.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 23 - Mar 24

Total with taxes and fees

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

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

### 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

$156 nightly

$176 total

Mar 23 - Mar 24

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/0d96bb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite | View from room](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/9102c136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/b2177890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/5468a801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Colle di Val d'Elsa

[](https://www.expedia.com/Colle-Di-Val-DElsa-Hotels-Palazzo-Pacini.h11807517.Hotel-Information)

9.8/10

Exceptional

(99 reviews)

"A nice blend of old world charm and modern conveniences. It is far from "

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

John

$100 nightly

$112 total

Apr 19 - Apr 20

Total with taxes and fees

[](https://www.expedia.com/Colle-Di-Val-DElsa-Hotels-Palazzo-Pacini.h11807517.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)

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

![Seasonal outdoor pool, open 7:30 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/bc0362da.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

$195 nightly

$224 total

Mar 23 - Mar 24

Total with taxes and fees

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

![Courtyard](https://images.trvl-media.com/lodging/2000000/1150000/1141800/1141734/7ee676c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1150000/1141800/1141734/ba86972f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1141800/1141734/f6917d90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1150000/1141800/1141734/bcf8fd1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Florence

[](https://www.expedia.com/Impruneta-Hotels-I-Parigi-Corbinelli.h1141734.Hotel-Information)

9.4/10

Exceptional

(162 reviews)

"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."

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

Tim

$75 nightly

$97 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Impruneta-Hotels-I-Parigi-Corbinelli.h1141734.Hotel-Information)

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

![Superior Room (Camera 2) | 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/3000000/2440000/2432300/2432264/920701e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Condo (Casa Palei B) | Premium bedding, down comforters, individually furnished, desk](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/c8b78159.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

$154 nightly

$170 total

Apr 6 - Apr 7

Total with taxes and fees

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

![Property amenity](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/dad23b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/150d969c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Tent | Cribs/infant beds, bed sheets](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/d1993efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/e7397564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Impruneta

[](https://www.expedia.com/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information)

8.0/10

Very Good

(60 reviews)

"Wonderful staff and great amenities!"

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

Chenjin

$44 nightly

$52 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information)

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

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

![In-room dining](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/d186b654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Townhouse in San Casciano in Val di Pesa

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

9.4/10

Exceptional

(25 reviews)

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

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

Raymundo

$79 nightly

$92 total

Mar 31 - Apr 1

Total with taxes and fees

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

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

![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)

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

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

### Residence in Impruneta

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

9.0/10

Wonderful

(14 reviews)

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

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

Lauren

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/06079da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/94c6df84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/60f29610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/cc13c05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Impruneta

[](https://www.expedia.com/Impruneta-Hotels-Relais-Villa-Olmo.h797278.Hotel-Information)

9.4/10

Exceptional

(229 reviews)

"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"

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

Cameron

$119 nightly

$134 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Impruneta-Hotels-Relais-Villa-Olmo.h797278.Hotel-Information)

![Panoramic Apartment | 2 bedrooms, Frette Italian sheets, hypo-allergenic bedding](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/de61baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Panoramic Apartment | 2 bedrooms, Frette Italian sheets, hypo-allergenic bedding](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/ac22c4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Residence in Impruneta

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

8.8/10

Excellent

(32 reviews)

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

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

Desiree

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

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2534200/2534128/954daca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/3000000/2540000/2534200/2534128/544f4406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/3000000/2540000/2534200/2534128/765657b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2534200/2534128/0ca7889f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Barberino Tavarnelle

[](https://www.expedia.com/Barberino-Tavarnelle-Hotels-Villa-San-Filippo.h2534128.Hotel-Information)

8.4/10

Very Good

(40 reviews)

"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."

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

Andrew

$120 nightly

$138 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Barberino-Tavarnelle-Hotels-Villa-San-Filippo.h2534128.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2532700/2532634/d1955947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2540000/2532700/2532634/7735ede4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room, Hill View | Minibar, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2540000/2532700/2532634/c765f486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2532700/2532634/12703fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Gimignano

[](https://www.expedia.com/San-Gimignano-Hotels-Antico-Borgo-Il-Cardino.h2532634.Hotel-Information)

9.4/10

Exceptional

(82 reviews)

"It was perfect for my one night stop before moving on to another location in Toscana."

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

Craig

$124 nightly

$143 total

Apr 16 - Apr 17

Total with taxes and fees

[](https://www.expedia.com/San-Gimignano-Hotels-Antico-Borgo-Il-Cardino.h2532634.Hotel-Information)

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

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

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

![Exterior](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/c92d2813.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-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information)

9.2/10

Wonderful

(82 reviews)

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

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

Ruben

$110 nightly

$125 total

Mar 25 - Mar 26

Total with taxes and fees

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

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

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

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/bdcda4ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Barberino Tavarnelle

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

9.4/10

Exceptional

(14 reviews)

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

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

Jessica

$147 nightly

$167 total

Apr 10 - Apr 11

Total with taxes and fees

[](https://www.expedia.com/Barberino-Tavarnelle-Hotels-Antica-Pieve-BB.h971821.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/a247f3f6.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)

![Exterior](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/c8ba4843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/26000000/25170000/25163600/25163522/05e1fe83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Castellina in Chianti

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

9.6/10

Exceptional

(15 reviews)

"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

$129 nightly

$147 total

Mar 28 - Mar 29

Total with taxes and fees

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

![Property amenity](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/55484b4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/a09ac8b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/2bf4d113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mobile Home Deluxe | View from room](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/ee50a2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Rignano sull'Arno

[](https://www.expedia.com/Rignano-SullArno-Hotels-Camping-Village-Il-Poggetto.h16157250.Hotel-Information)

8.0/10

Very Good

(65 reviews)

"Pet friendly and clean"

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

Nancy

$62 nightly

$72 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Rignano-SullArno-Hotels-Camping-Village-Il-Poggetto.h16157250.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)

![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)

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

(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

$162 nightly

$188 total

Mar 30 - Mar 31

Total with taxes and fees

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

![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)

![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)

![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)

### Apartment in Reggello

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

$139 nightly

$159 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Reggello-Hotels-LE-BOTTI-FIORENTINE.h125624410.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=2026-04-05&endDate=2026-04-06&regionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=VILLA)

Apartments

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Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=APART_HOTEL)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=RESIDENCE)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=CONDO)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=CABIN)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=CHALET)

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## Top Chianti Region Hotel Reviews

![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/f80bb145_y.jpg)

### Castello di Fonterutoli Wine Resort

10/10 Excellent

"Le personnel est super accueillant. L’endroit est paradisiaque, la bouffe est excellente et le vin divin."

[](https://expedia.com/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information)

![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf_y.jpg)

### Castello Vicchiomaggio

10/10 Excellent

"One of the most amazing experiences we've ever had. I recommend this place 100%. The castle is beautiful, the service is amazing, the suites are beautiful, and the wine tour with lunch is fantastic. "

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

![Borgo Del Cabreo](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/6c72b535_y.jpg)

### Borgo Del Cabreo

10/10 Excellent

"Borgo del Cabreo was our favorite place we stayed on our trip to Italy in March. Every detail of the Borgo was thoughtfully curated and is situated in the most beautiful setting in the Chianti region. The rooms and bathrooms were big. The king size bed was very comfortable. The breakfast was delicious in the most idyllic setting. The city center of Florence was loud at night even in March, so coming here was very restorative to my soul. The sounds of nature, birds singing, the idyllic scenary, was a wonderful contrast to Florence. We had the most wonderful dinner and wine at their sister property Pietra del Cabreo. My kids and I would return to Italy just to stay here again. "

[](https://expedia.com/Greve-In-Chianti-Hotels-Borgo-Del-Cabreo.h17963776.Hotel-Information)

![Villa I Barronci Resort & Spa](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/57a598f5_y.jpg)

### Villa I Barronci Resort & Spa

10/10 Excellent

"Wonderful stay. Clean rooms. Such friendly and accommodating staff. The restaurant was temporarily closed but they still made sure there was a full breakfast buffet every morning and dinner had a set menu option each night. The pool was open and warm! Lots of parking if you’re renting a car. Great proximity to Florence and rest of Tuscany if you plan to tour around yourself. "

[](https://expedia.com/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information)

![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eac4992_y.jpg)

### Salvadonica - Borgo del Chianti

10/10 Excellent

"We loved our time at Salvadonica. The food was excellent and we particularly enjoyed the cooking class. I would love to go back during grape and olive harvesting season. The staff was friendly and very helpful "

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

![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/994bfd62_y.jpg)

### Villa Casagrande Resort & SPA

10/10 Excellent

"The staff was extremely knowledgeable, friendly, and available when we had questions. The room was clean and the bed was comfortable. The property was also well maintained and beautiful."

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

![hu Firenze Certosa camping in town](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/dad23b8c_y.jpg)

### hu Firenze Certosa camping in town

10/10 Excellent

"Fantastic! The staff was very helpfull, the rooms were impeacable (and warm) and the dinner at the restaurant was delicious. Better than an hotel in our opinion. Congrats! The only drawback as lack of EV charger... but they said it was coming.."

[](https://expedia.com/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information)

![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/2f9ea910_y.jpg)

### Hotel Toscana Ambassador

10/10 Excellent

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

[](https://expedia.com/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.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 Chianti Region

**Everything you need to know about Chianti Region 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 Chianti Region 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 Chianti Region vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chianti Region vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chianti Region. 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 Chianti Region 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 $52 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 Chianti Region rentals**

At Expedia, we put the best Chianti Region 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 Chianti Region 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 Chianti Region 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 Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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- [B&B in Chianti Region ](https://expedia.com/Chianti-Region-Bed-And-Breakfast.d603148-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Chianti Region ](https://expedia.com/Chianti-Region-Cottages.d603148-aaCottages.Travel-Guide-Accommodation)
- [Town Houses in Chianti Region ](https://expedia.com/Chianti-Region-Town-Houses.d603148-aaTownHouses.Travel-Guide-Accommodation)
- [Residences in Chianti Region ](https://expedia.com/Chianti-Region-Residences.d603148-aaResidences.Travel-Guide-Accommodation)
- [Country Houses in Chianti Region ](https://expedia.com/Chianti-Region-Country-House.d603148-aaCountryHouse.Travel-Guide-Accommodation)
- [Guest Houses in Chianti Region ](https://expedia.com/Chianti-Region-Guest-Houses.d603148-aaGuestHouses.Travel-Guide-Accommodation)
- [Aparthotels in Chianti Region ](https://expedia.com/Chianti-Region-Apart-Hotels.d603148-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Chianti Region ](https://expedia.com/Chianti-Region-Inns.d603148-aaInns.Travel-Guide-Accommodation)
- [RV Parks in Chianti Region ](https://expedia.com/Chianti-Region-RV-Parks.d603148-aaRVParks.Travel-Guide-Accommodation)
- [Lodges in Chianti Region ](https://expedia.com/Chianti-Region-Lodges.d603148-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Chianti Region ](https://expedia.com/Chianti-Region-Resorts.d603148-aaResorts.Travel-Guide-Accommodation)

### Expedia's Latest Trends

Hotels

- [Hotels in Brunello di Montalcino Wine Area](https://expedia.com/Brunello-Di-Montalcino-Wine-Area-Hotels.d6342620.Travel-Guide-Hotels)
- [Duomo Hotels](https://expedia.com/Duomo-Florence-Hotels.0-n6084346-0.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Maremma](https://expedia.com/Maremma-Hotels-Winery-Hotel.0-0-d553248634855578977-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Val d'Orcia](https://expedia.com/Val-DOrcia-Hotels-Winery-Hotel.0-0-d6047918-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Winery Hotels in Brunello di Montalcino Wine Area](https://expedia.com/Brunello-Di-Montalcino-Wine-Area-Hotels-Winery-Hotel.0-0-d6342620-tWineryHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Laundry Facilities in Brunello di Montalcino Wine Area](https://expedia.com/Brunello-Di-Montalcino-Wine-Area-Hotels-Hotels-With-Laundry-Facilities.0-0-d6342620-tHotelswithLaundryFacilities.Travel-Guide-Filter-Hotels)
- [Golf Hotels in Val d'Orcia](https://expedia.com/Val-DOrcia-Hotels-Golf-Hotel.0-0-d6047918-tGolfHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Elba Island](https://expedia.com/Elba-Island-Hotels.d1090.Travel-Guide-Hotels)
- [Historic Centre of Florence Hotels](https://expedia.com/Historic-Centre-Of-Florence-Florence-Hotels.0-n6141938-0.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Val d'Orcia](https://expedia.com/Val-DOrcia-Hotels-Luxury-Hotel.0-0-d6047918-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Maremma](https://expedia.com/Maremma-Hotels-Couples-Resorts-Hotels.0-0-d553248634855578977-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Pet-friendly Hotels in Maremma](https://expedia.com/Maremma-Hotels-Pet-Friendly-Hotel.0-0-d553248634855578977-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)

Flights

- [Cheap Flights to Elba Island](https://expedia.com/Cheap-Flights-To-Elba-Island.d1090.Travel-Guide-Flights)

Cars

- [Car rentals in Elba Island](https://expedia.com/Car-Rentals-In-Elba-Island.d1090.Car-Rental-Guide)
- [ZezGo Car Rentals In Crete Senesi](https://expedia.com/ZezGo-Car-Rentals-In-Crete-Senesi.d6342453-c1122.Car-Rental-Guide-Suppliers)
- [Car rental Florence Airport (FLR)](https://expedia.com/Car-Rentals-In-Peretola.d5393478.Car-Rental-Guide)
- [Car rentals near Port of Livorno](https://expedia.com/Car-Rentals-In-Port-Of-Livorno.d6190962.Car-Rental-Guide)
- [Redspot Car Rentals In Crete Senesi](https://expedia.com/Redspot-Car-Rentals-In-Crete-Senesi.d6342453-c1078.Car-Rental-Guide-Suppliers)
- [Avis Car Rentals In Elba Island](https://expedia.com/Avis-Car-Rentals-In-Elba-Island.d1090-c41.Car-Rental-Guide-Suppliers)
- [Movida Car Rentals In Crete Senesi](https://expedia.com/Movida-Car-Rentals-In-Crete-Senesi.d6342453-c1049.Car-Rental-Guide-Suppliers)
- [Car rentals in Santa Maria Novella](https://expedia.com/Car-Rentals-In-Santa-Maria-Novella.d6084343.Car-Rental-Guide)

Packages

- [Terme di Saturnia](https://expedia.com/Terme-Di-Saturnia-Manciano.d6150383.Vacation-Attraction)
- [Piscine Termali Theia](https://expedia.com/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction)
- [Elba Island All Inclusive Vacation Packages](https://expedia.com/lp/theme-vacations/kid-friendly-vacations/1090/Elba-Island)
- [Brunello di Montalcino Wine Area Vacation](https://expedia.com/Brunello-Di-Montalcino-Wine-Area.d6342620.Destination-Travel-Guides)

General

- [Visit Porto Santo Stefano](https://expedia.com/Porto-Santo-Stefano.dx6025634)
- [Visit Brunello di Montalcino Wine Area](https://expedia.com/Brunello-Di-Montalcino-Wine-Area.dx6342620)
- [Visit Maremma](https://expedia.com/Maremma.dx553248634855578977)
- [Visit Elba Island](https://expedia.com/Elba-Island.dx1090)
- [Visit Santa Maria Novella](https://expedia.com/Florence-Santa-Maria-Novella.dx6084343)

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