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

Search Apartment Rentals in Chianti Region

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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 CA $162
CA $187 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $157
CA $211 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $163
CA $187 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is CA $228
CA $332 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $118
CA $201 total
includes taxes & fees
Nov 11 - Nov 12
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.
The price is CA $181
CA $263 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is CA $135
CA $193 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $134
CA $151 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $153
CA $173 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $227
CA $258 total
includes taxes & fees
Nov 10 - Nov 11
LE BOTTI FIORENTINE
Property grounds

11. Sonia Cosy Fresh Apartment with Garden

Sonia Cosy Fresh Apartment with Garden
Greve in Chianti
The price is CA $293
CA $501 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $99
CA $105 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $117
CA $134 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $79
CA $164 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $236
CA $443 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $139
CA $145 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $136
CA $235 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $198
CA $320 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $95
CA $147 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is CA $140
CA $144 total
includes taxes & fees
Nov 10 - Nov 11
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Find out more about Chianti Region

Chianti Region Apartments information

Number of reviews
32
Accommodation
435 Apartments
Lowest Price
CA $105
Highest Price
CA $501

Explore a world of travel with Expedia