Chianti Region Holiday Rentals

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Our top choices for Chianti Region holiday rentals

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is S$196
includes taxes & fees
10 Apr - 11 Apr
Villa Cassia di Baccano

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is S$255
includes taxes & fees
11 Apr - 12 Apr
Riserva di Fizzano Residence

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (231 reviews)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
United States
Cameron
The price is S$255
includes taxes & fees
27 Apr - 28 Apr
Relais Villa Olmo

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 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
rose
The price is S$256
includes taxes & fees
9 Apr - 10 Apr
Villa il Fedino

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 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
Amelia
The price is S$226
includes taxes & fees
20 Apr - 21 Apr
Villa di Sotto

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is S$135
includes taxes & fees
23 Apr - 24 Apr
Palazzo Pacini

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 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
Massimo
The price is S$289
includes taxes & fees
7 Apr - 8 Apr
Borgo Argenina

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is S$168
includes taxes & fees
14 Apr - 15 Apr
B&B La Fonte del Machiavelli

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is S$239
includes taxes & fees
22 Apr - 23 Apr
Villa Curina Resort

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 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
Perry
The price is S$226
includes taxes & fees
11 Apr - 12 Apr
L' Eroico

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.4 out of 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
Raymundo
The price is S$149
includes taxes & fees
13 Apr - 14 Apr
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 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
Jessica
The price is S$213
includes taxes & fees
27 Apr - 28 Apr
Antica Pieve B&B

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 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
Andrew
The price is S$136
includes taxes & fees
13 Apr - 14 Apr
Villa San Filippo

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is S$148
includes taxes & fees
20 Apr - 21 Apr
Antico Borgo il Cardino

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.4 out of 10, Exceptional, (163 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is S$137
includes taxes & fees
7 Apr - 8 Apr
I Parigi Corbinelli

Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.0 out of 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
Lauren
The price is S$299
includes taxes & fees
12 Apr - 13 Apr
Rocca Palazzaccio

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is S$131
includes taxes & fees
10 Apr - 11 Apr
Mariani Bed & Breakfast

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (32 reviews)
"Such a cute little place! Very clean and easy to get around! Would highly recommend!"
United States
Desiree
The price is S$121
includes taxes & fees
7 Apr - 8 Apr
Residence Il Connubio

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is S$206
includes taxes & fees
7 Apr - 8 Apr
Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (71 reviews)
"Very nice place"
United States
Maria
The price is S$133
includes taxes & fees
12 Apr - 13 Apr
Relais Villa Belvedere
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 Chianti Region Hotel Reviews