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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chianti Region vacation rentals

A table with breakfast items and a view of rolling hills.

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
$73 nightly
The price is $82
Oct 13 - Oct 14
Total with taxes and fees
Chianti Village Morrocco
A villa with a swimming pool, outdoor seating, and a tennis court.

2. 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
$139 nightly
The price is $158
Oct 4 - Oct 5
Total with taxes and fees
Villa Curina Resort
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$206 nightly
The price is $226
Oct 1 - Oct 2
Total with taxes and fees
Villa di Sotto
A stone building with a garden in front.

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
$238 nightly
The price is $271
Oct 1 - Oct 2
Total with taxes and fees
Borgo Argenina
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

5. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
$81 nightly
The price is $94
Oct 15 - Oct 16
Total with taxes and fees
Mariani Bed & Breakfast
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

6. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
$140 nightly
The price is $158
Oct 21 - Oct 22
Total with taxes and fees
Relais Villa Olmo
Exterior

7. 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
$105 nightly
The price is $120
Oct 21 - Oct 22
Total with taxes and fees
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

8. 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
$106 nightly
The price is $130
Oct 6 - Oct 7
Total with taxes and fees
I Parigi Corbinelli
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

9. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
$118 nightly
The price is $134
Oct 7 - Oct 8
Total with taxes and fees
B&B La Fonte del Machiavelli
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

10. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$113 nightly
The price is $126
Oct 31 - Nov 1
Total with taxes and fees
Palazzo Pacini
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

11. 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
$152 nightly
The price is $168
Oct 5 - Oct 6
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
A stone building with a yellow sign reading "b&b erioico".

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
$142 nightly
The price is $165
Oct 9 - Oct 10
Total with taxes and fees
L' Eroico
A dining area with a table set for two, featuring a view of greenery through a window.

13. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
$158 nightly
The price is $178
Oct 6 - Oct 7
Total with taxes and fees
La Locanda di Pietracupa
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

14. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$167 nightly
The price is $186
Oct 8 - Oct 9
Total with taxes and fees
Riserva di Fizzano Residence
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

15. 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
$89 nightly
The price is $104
Oct 31 - Nov 1
Total with taxes and fees
Villa San Filippo
A pool area with a water slide and a stage for performances.

16. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (333 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
$63 nightly
The price is $71
Oct 2 - Oct 3
Total with taxes and fees
Hu Norcenni Girasole Village
A water park with a pool, slides, and a wooden deck area.

17. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (108 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
$41 nightly
The price is $48
Oct 13 - Oct 14
Total with taxes and fees
hu Firenze Certosa camping in town
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

18. 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
$99 nightly
The price is $110
Oct 30 - Oct 31
Total with taxes and fees
Relais Villa Belvedere
An arched entrance with a lantern above, flanked by two potted plants.

19. 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
$215 nightly
The price is $241
Oct 6 - Oct 7
Total with taxes and fees
Villa il Fedino
A cozy living room with a stone wall, a wine rack, and two sofas.

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
$191 nightly
The price is $210
Oct 13 - Oct 14
Total with taxes and fees
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.
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Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"Excellent dinner, spacious rooms, pol and jacuzzi, and incredible views!"
Danny 1-night trip
Posted 2 days ago
Villa I Barronci Resort & Spa

Find out more about Chianti Region

Everything you need to know about Chianti Region vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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