A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chianti Region vacation rentals

View from room

1. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ￥13,837
￥15,592 total
includes taxes & fees
Aug 28 - Aug 29
Chianti Village Morrocco
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (38 reviews)
"Great spot"
Canada
Philippe
The price is ￥25,734
￥28,307 total
includes taxes & fees
Sep 21 - Sep 22
Villa di Sotto
Garden view

3. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (49 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ￥12,895
￥15,297 total
includes taxes & fees
Sep 21 - Sep 22
Villa San Filippo
Courtyard

4. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (169 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is ￥15,672
￥19,471 total
includes taxes & fees
Aug 30 - Aug 31
I Parigi Corbinelli
Free daily buffet breakfast

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is ￥47,608
￥53,113 total
includes taxes & fees
Aug 31 - Sep 1
Terre di Baccio
Exterior

6. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (329 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is ￥12,047
￥13,809 total
includes taxes & fees
Aug 27 - Aug 28
Hu Norcenni Girasole Village
Exterior

7. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is ￥40,297
￥45,813 total
includes taxes & fees
Aug 30 - Aug 31
Borgo Argenina
Aerial view

8. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ￥31,461
￥34,979 total
includes taxes & fees
Sep 8 - Sep 9
Riserva di Fizzano Residence
Lounge

9. 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 ￥14,771
￥16,990 total
includes taxes & fees
Sep 4 - Sep 5
Mariani Bed & Breakfast
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

10. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
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 ￥19,772
￥22,494 total
includes taxes & fees
Aug 28 - Aug 29
Residenzia del Sogno
Property amenity

11. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very Good, (98 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is ￥8,600
￥10,017 total
includes taxes & fees
Aug 27 - Aug 28
hu Firenze Certosa camping in town
Aerial view

12. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (75 reviews)
"Beautiful property"
Canada
Mary
The price is ￥30,366
￥34,144 total
includes taxes & fees
Aug 30 - Aug 31
Villa Curina Resort
Breakfast, lunch and dinner served

13. La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.6 out of 10, Exceptional, (38 reviews)
"Charming and very original. Great warmth from the staff and very helpful. Enjoyed the room and restaurant at and surrounding towns."
Australia
Con
The price is ￥28,095
￥31,649 total
includes taxes & fees
Aug 27 - Aug 28
La Locanda di Pietracupa
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

14. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is ￥16,460
￥18,477 total
includes taxes & fees
Aug 27 - Aug 28
Borgo di Erboli
Exterior

15. 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
9.2 out of 10, Wonderful, (27 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 ￥18,502
￥21,097 total
includes taxes & fees
Sep 2 - Sep 3
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Terrace/patio

16. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ￥17,963
￥20,131 total
includes taxes & fees
Sep 2 - Sep 3
Palazzo Pacini
Exterior detail

17. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (24 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is ￥14,985
￥29,831 total
includes taxes & fees
Aug 27 - Aug 28
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Exterior

18. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is ￥24,231
￥28,141 total
includes taxes & fees
Aug 27 - Aug 28
L' Eroico
Front of property

19. 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 ￥27,990
￥30,789 total
includes taxes & fees
Sep 2 - Sep 3
Relais Villa Belpoggio - Residenza d'Epoca
Property amenity

20. Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very Good, (75 reviews)
"Nice property, very reasonable price"
United States
Alex
The price is ￥10,039
￥11,601 total
includes taxes & fees
Aug 31 - Sep 1
Camping Village Il Poggetto.
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

Borgo Vescine

Borgo Vescine

10/10 Excellent
"The resort is amazingly restored and preserved and has a wonderful family feel while remains very private and has an exclusive appeal. If it is at all possible I would highly recommend the family style dinner served on Monday night which is available to all the guests. It fascinating to interact with the people who are here for the first time or revisiting for the 30th time."
Bryan 2-night trip
Posted 10 hours ago
Borgo Vescine

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