Chianti Region Vacation Rentals

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Our top choices for Chianti Region vacation rentals

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is CA $219
CA $241 total
includes taxes & fees
Mar 10 - Mar 11
Villa Cassia di Baccano

Residence in Barberino Tavarnelle

Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco

Townhouse in Castelnuovo Berardenga

Villa di Sotto
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
Villa di Sotto

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (99 reviews)
"Great people, great location great service"
Canada
James
The price is CA $207
CA $235 total
includes taxes & fees
Feb 28 - Mar 1
Villa il Fedino

Townhouse in San Casciano in Val di Pesa

B&B La Fonte del Machiavelli
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 CA $149
CA $171 total
includes taxes & fees
Mar 13 - Mar 14
B&B La Fonte del Machiavelli
8.0 out of 10, Very good, (59 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
The price is CA $58
CA $69 total
includes taxes & fees
Mar 1 - Mar 2
hu Firenze Certosa camping in town

Townhouse in Florence

I Parigi Corbinelli
9.4 out of 10, Exceptional, (162 reviews)
"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."
Australia
Tim
The price is CA $108
CA $138 total
includes taxes & fees
Mar 5 - Mar 6
I Parigi Corbinelli

Residence in Colle di Val d'Elsa

Palazzo Pacini
9.8 out of 10, Exceptional, (98 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is CA $158
CA $178 total
includes taxes & fees
Mar 2 - Mar 3
Palazzo Pacini

Townhouse in San Casciano in Val di Pesa

B&B Le Dimore Mezza Costa
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 CA $118
CA $137 total
includes taxes & fees
Mar 9 - Mar 10
B&B Le Dimore Mezza Costa

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 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
Perry
L' Eroico

Townhouse in Barberino Tavarnelle

Antica Pieve B&B
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 CA $132
CA $184 total
includes taxes & fees
Feb 28 - Mar 1
Antica Pieve B&B

Residence in Impruneta

Residence Il Connubio
3.0 star property
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
Residence Il Connubio

Apartment in Pergine Valdarno

Casa Vacanze Le Fornaci
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is CA $178
CA $200 total
includes taxes & fees
Feb 28 - Mar 1
Casa Vacanze Le Fornaci

Apartment in Reggello

LE BOTTI FIORENTINE
The price is CA $166
CA $191 total
includes taxes & fees
Mar 30 - Mar 31
LE BOTTI FIORENTINE

Townhouse in Barberino Tavarnelle

La Locanda di Pietracupa
9.4 out of 10, Exceptional, (35 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa

Townhouse in Castellina in Chianti

Residenzia del Sogno
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is CA $178
CA $203 total
includes taxes & fees
Mar 16 - Mar 17
Residenzia del Sogno
The price is CA $744
CA $888 total
includes taxes & fees
Feb 28 - Mar 1
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

Aparthotel in Figline e Incisa Valdarno

Relais Villa Belvedere
9.2 out of 10, Wonderful, (71 reviews)
"Very nice place"
United States
Maria
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

Find out more about Chianti Region

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 Chianti Region. 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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