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

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chianti Region apartments

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

1. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is SAR 429
SAR 497 total
includes taxes & fees
16 Nov - 17 Nov
Casa Vacanze Squarcialupi
A kitchen area with a vase of dried plants on a tray, a microwave, and a window with curtains.

2. Vale's House

Vale's House
Certaldo
The price is SAR 418
SAR 561 total
includes taxes & fees
12 Nov - 13 Nov
Vale's House
A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.

3. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
9.8 out of 10, Exceptional, (9 reviews)
"Very welcoming host, lovely stone wall in the apartment and the beautiful bathroom."
United States
Kathleen F.
The price is SAR 433
SAR 496 total
includes taxes & fees
10 Nov - 11 Nov
Old medieval apartment
A wooden deck with a pool, a bottle of champagne, two wine glasses, a bowl of strawberries, and a red flower.

4. Malvasia holiday home with mini-pool in the center of Greve in Chianti

Malvasia holiday home with mini-pool in the center of Greve in Chianti
Greve in Chianti
10.0 out of 10, Exceptional, (5 reviews)
"Loved our stay here! Check in and out was easy. I can’t wait to come back and visit again."
United States
Amanda Z.
Malvasia holiday home with mini-pool in the center of Greve in Chianti
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

5. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Castellina in Chianti
The price is SAR 312
SAR 533 total
includes taxes & fees
11 Nov - 12 Nov
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
A restaurant with brick arches, wooden tables, and a bar area with wine bottles.

6. Gallo Nero apartment 2/4 people close to the center of Greve in Chianti

Gallo Nero apartment 2/4 people close to the center of Greve in Chianti
Greve in Chianti
10.0 out of 10, Exceptional, (1 review)
"Clean simple central location. Plenty of parking and a safe neighbourhood."
Canada
Brent F.
Gallo Nero apartment 2/4 people close to the center of Greve in Chianti
An aerial view of a historic estate with a central courtyard, surrounding buildings, and vineyards.

7. Wake Up to Chianti Vineyards · Authentic Tuscan Apt · A/C · Sleeps 4

Wake Up to Chianti Vineyards · Authentic Tuscan Apt · A/C · Sleeps 4
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (2 reviews)
"Awesome host! He was incredibly responsive and helpful throughout our stay. The location was great, with several excellent dining options nearby. We would definitely stay here again if we’re ever back in town!"
United States
Edwin B.
Wake Up to Chianti Vineyards · Authentic Tuscan Apt · A/C · Sleeps 4
A view from a window overlooking a rural landscape with a tall tree and distant hills.

8. A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi

A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
Cavriglia
A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

9. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 reviews)
"Very nice hotel with friendly stad"
Denmark
Lisette
The price is SAR 407
SAR 460 total
includes taxes & fees
18 Nov - 19 Nov
Casa Vacanze Le Fornaci
A wooden structure with a circular door, surrounded by a garden with string lights and a view of distant mountains.

10. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is SAR 597
SAR 678 total
includes taxes & fees
10 Nov - 11 Nov
LE BOTTI FIORENTINE
Property grounds

11. Sonia Cosy Fresh Apartment with Garden

Sonia Cosy Fresh Apartment with Garden
Greve in Chianti
The price is SAR 778
SAR 1,330 total
includes taxes & fees
10 Nov - 11 Nov
Sonia Cosy Fresh Apartment with Garden
A swimming pool with lounge chairs and umbrellas, a stone building with green shutters, and a clear blue sky.

12. Lilla Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi & Air Conditioning

Lilla Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi & Air Conditioning
Barberino Val d'Elsa
Lilla Room 'Borghetto San Filippo' with Shared Pool, Wi-Fi & Air Conditioning
Private kitchen

13. A Stay at Le Mortinete Farm: Madre Mignola

A Stay at Le Mortinete Farm: Madre Mignola
Toscana
A Stay at Le Mortinete Farm: Madre Mignola
A room with a wooden ceiling beam, a framed picture of Tuscany, a clock, and a shelf with a bottle and a candle.

14. Torre 43 - One Bedroom Apartment, Sleeps 4

Torre 43 - One Bedroom Apartment, Sleeps 4
Montevarchi
The price is SAR 209
SAR 435 total
includes taxes & fees
11 Nov - 12 Nov
Torre 43 - One Bedroom Apartment, Sleeps 4
A rural road leading to a stone building with a metal gate, surrounded by lush greenery and hills in the background.

15. A Dream in Chianti in Radda - 3 separate bedrooms with private bathrooms and TVs

A Dream in Chianti in Radda - 3 separate bedrooms with private bathrooms and TVs
Toscana
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was perfect for what we needed. It was very clean and very comfortable. The beds were comfortable and the bathrooms were quite roomy and even had a place for your shampoo and soap in the shower. "
United States
Wendy T.
The price is SAR 628
SAR 1,167 total
includes taxes & fees
10 Nov - 11 Nov
A Dream in Chianti in Radda - 3 separate bedrooms with private bathrooms and TVs
A stone structure with steps leading up to a wall, surrounded by greenery and trees.

16. Apartment 'Cantina' with Shared Garden and Wi-Fi

Apartment 'Cantina' with Shared Garden and Wi-Fi
Terranuova Bracciolini
Apartment 'Cantina' with Shared Garden and Wi-Fi
A modern bedroom with a curved bed, a large mirror, and a jungle-themed mural.

17. Colle di Val d'Elsa - Siena - White Apartment - D

Colle di Val d'Elsa - Siena - White Apartment - D
Colle di Val d'Elsa
Colle di Val d'Elsa - Siena - White Apartment - D
A rectangular swimming pool with a clear blue water surface, surrounded by a concrete deck. There are lounge chairs and two green umbrellas on the deck. The pool is set against a backdrop of lush green trees and a grassy hill.

18. Apartment 'San Bartolo 1C' with Shared Pool, Wi-Fi, and Air Conditioning

Apartment 'San Bartolo 1C' with Shared Pool, Wi-Fi, and Air Conditioning
Barberino Val d'Elsa
Apartment 'San Bartolo 1C' with Shared Pool, Wi-Fi, and Air Conditioning
A narrow stone pathway flanked by rustic stone buildings with wooden shutters and potted plants.

19. Casina 57 - One Bedroom Apartment, Sleeps 2

Casina 57 - One Bedroom Apartment, Sleeps 2
Poggio di Loro
Casina 57 - One Bedroom Apartment, Sleeps 2
A hotel entrance with wooden shutters, an air conditioning unit, and potted plants.

20. Apartment 'Casa Parco Dell'Elsa' with Wi-Fi and Air Conditioning

Apartment 'Casa Parco Dell'Elsa' with Wi-Fi and Air Conditioning
Colle di Val d'Elsa
Apartment 'Casa Parco Dell'Elsa' with Wi-Fi and Air Conditioning
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

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

10/10 Excellent
"Excellent unique property with top notch service, attention and experiences. The food and staff at Osteria Il Borro were exceptional!"
Kelly 2-night trip
Posted 16 hours ago
Il Borro - Relais & Châteaux