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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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 428
SAR 496 total
includes taxes & fees
6 Nov - 7 Nov
Casa Vacanze Squarcialupi
A stone-walled outdoor dining area with a table and chairs, a lantern, and a door leading to an interior space.

2. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is SAR 398
SAR 1,490 total
includes taxes & fees
23 Oct - 24 Oct
Teranga in Chianti - Parking & Garden 3 BR
A bedroom with a bed, a chair, a bedside table, and a window.

3. Panzano34 A Charming Loft in the Heart of Chianti

Panzano34 A Charming Loft in the Heart of Chianti
Greve in Chianti
Panzano34 A Charming Loft in the Heart of Chianti
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

4. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is SAR 239
SAR 381 total
includes taxes & fees
15 Oct - 16 Oct
Borgo Antico Residence
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

5. 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 430
SAR 486 total
includes taxes & fees
17 Oct - 18 Oct
Casa Vacanze Le Fornaci
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

6. 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 349
SAR 561 total
includes taxes & fees
9 Nov - 10 Nov
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
A hotel room with a bed, a desk, a chair, a lamp, and a painting on the wall.

7. Teranga in Chianti - Parking & Garden 3 BR, BarberinoTavarnelle, Italy

Teranga in Chianti - Parking & Garden 3 BR, BarberinoTavarnelle, Italy
Tavarnelle Val di Pesa
Teranga in Chianti - Parking & Garden 3 BR, BarberinoTavarnelle, Italy
A covered outdoor seating area with a wooden deck, glass walls, and white chairs.

8. ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve

ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve
Greve in Chianti
ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve
A terrace with outdoor seating, a view of a historic building, and a clear sky.

9. Casa Falorni, 4 - Cassero - Bilocale

Casa Falorni, 4 - Cassero - Bilocale
Greve in Chianti
Casa Falorni, 4 - Cassero - Bilocale
A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.

10. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
9.8 out of 10, Exceptional, (8 reviews)
"Very welcoming host, lovely stone wall in the apartment and the beautiful bathroom."
United States
Kathleen F.
The price is SAR 435
SAR 528 total
includes taxes & fees
20 Oct - 21 Oct
Old medieval apartment
A view from a window overlooking a rural landscape with a tall tree and distant hills.

11. 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 SAR 357
SAR 433 total
includes taxes & fees
1 Nov - 2 Nov
A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
A wooden structure with a circular door, surrounded by a garden with string lights and a view of distant mountains.

12. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is SAR 570
SAR 648 total
includes taxes & fees
21 Oct - 22 Oct
LE BOTTI FIORENTINE
An aerial view of a historic estate with a central courtyard, surrounding buildings, and vineyards.

13. 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 SAR 416
SAR 601 total
includes taxes & fees
21 Oct - 22 Oct
Wake Up to Chianti Vineyards · Authentic Tuscan Apt · A/C · Sleeps 4
A table set with a wine bottle, glasses, and a plate of food in an outdoor setting with greenery and a vineyard in the background.

14. Bacco apartment 4/6 people with spacious terrace in Greve in Chianti

Bacco apartment 4/6 people with spacious terrace in Greve in Chianti
Greve in Chianti
The price is SAR 568
SAR 904 total
includes taxes & fees
11 Oct - 12 Oct
Bacco apartment 4/6 people with spacious terrace in Greve in Chianti
A hallway with a wooden bench, a chandelier, and a wall-mounted picture.

15. Le Mortinete Farmstay: Leccino

Le Mortinete Farmstay: Leccino
Toscana
The price is SAR 299
SAR 775 total
includes taxes & fees
11 Oct - 12 Oct
Le Mortinete Farmstay: Leccino
A compact kitchen with a wooden countertop, stainless steel appliances, and a modern design.

16. Cennano Suite - enter apartment

Cennano Suite - enter apartment
Montevarchi
10.0 out of 10, Exceptional, (3 reviews)
"After and before the tourist rushes of Florence. I enjoyed a few very quiet and relaxing days in a beautiful and spacious place. "
Germany
Judith T.
The price is SAR 164
SAR 408 total
includes taxes & fees
8 Nov - 9 Nov
Cennano Suite - enter apartment
A cozy living room with a sofa and a dining area with a table and chairs.

17. A cozy apartment in the heart of Tuscany, with a view of San Gimignano.

A cozy apartment in the heart of Tuscany, with a view of San Gimignano.
Toscana
The price is SAR 379
SAR 631 total
includes taxes & fees
7 Nov - 8 Nov
A cozy apartment in the heart of Tuscany, with a view of San Gimignano.
A swimming pool with lounge chairs and umbrellas, a stone building with green shutters, and a clear blue sky.

18. 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
Living area

19. Casa Castagna - appartamento nella Val d'Elsa

Casa Castagna - appartamento nella Val d'Elsa
Colle val d'Elsa
Casa Castagna - appartamento nella Val d'Elsa
A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.

20. Colle di Val d'Elsa - Siena - Apt Rose - B

Colle di Val d'Elsa - Siena - Apt Rose - B
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"The host is excellent. Perfect English and Italian. Thoughtful and great communication. Parking instructions were accurate. The apartment was beautiful and the bed was comfortable. The apartment is walkable to dining and shopping. The street is steep and the nearby medievale hill town is steeper. While we loved walking up to the hill town everyday, we liked the variety of dining and shopping near the apartment."
United States
Tamara C.
The price is SAR 277
SAR 571 total
includes taxes & fees
11 Oct - 12 Oct
Colle di Val d'Elsa - Siena - Apt Rose - B
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

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."
Frank 4-night trip
Posted 1 day ago
Castello Vicchiomaggio