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

Chianti Region Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chianti Region holiday rentals

1. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is NZ$145
includes taxes & fees
14 Oct - 15 Oct
Chianti Village Morrocco

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is NZ$382
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto

3. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is NZ$309
includes taxes & fees
27 Sept - 28 Sept
Villa Curina Resort

4. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is NZ$350
includes taxes & fees
28 Sept - 29 Sept
Borgo Argenina

5. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is NZ$172
includes taxes & fees
7 Oct - 8 Oct
Mariani Bed & Breakfast

6. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (266 reviews)
"Very friendly and clean."
United States
Mohamed
The price is NZ$334
includes taxes & fees
19 Oct - 20 Oct
Relais Villa Olmo

7. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (85 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is NZ$224
includes taxes & fees
5 Oct - 6 Oct
B&B La Fonte del Machiavelli

8. 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 NZ$305
includes taxes & fees
29 Sept - 30 Sept
Relais Villa Belpoggio - Residenza d'Epoca

9. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is NZ$641
includes taxes & fees
25 Sept - 26 Sept
Terre di Baccio

10. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is NZ$224
includes taxes & fees
6 Oct - 7 Oct
I Parigi Corbinelli

11. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (75 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is NZ$201
includes taxes & fees
18 Oct - 19 Oct
Relais Villa Belvedere

12. 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 NZ$321
includes taxes & fees
25 Sept - 26 Sept
L' Eroico

13. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (107 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is NZ$93
includes taxes & fees
15 Oct - 16 Oct
hu Firenze Certosa camping in town

14. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (39 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is NZ$391
includes taxes & fees
29 Sept - 30 Sept
Riserva di Fizzano Residence

15. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is NZ$437
includes taxes & fees
19 Oct - 20 Oct
Villa il Fedino

16. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is NZ$327
includes taxes & fees
26 Sept - 27 Sept
La Locanda di Pietracupa

17. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (53 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is NZ$185
includes taxes & fees
25 Oct - 26 Oct
Villa San Filippo

18. 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 NZ$250
includes taxes & fees
27 Sept - 28 Sept
Residenzia del Sogno

19. 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, (28 reviews)
"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."
United States
Erick
The price is NZ$240
includes taxes & fees
20 Oct - 21 Oct
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

20. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (26 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$330
includes taxes & fees
10 Oct - 11 Oct
Villa Cassia di Baccano
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Find out more about Chianti Region

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chianti Region holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chianti Region. 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 Chianti Region. 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 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 holiday 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 Chianti Region short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia