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

Chianti Region Vacation Rentals

  • 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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chianti Region vacation rentals

A villa with a swimming pool, outdoor seating, and a tennis court.

1. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (82 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is ₩173,619
₩196,890 total
includes taxes & fees
Oct 30 - Oct 31
Villa Curina Resort
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

2. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is ₩357,751
₩399,435 total
includes taxes & fees
Oct 30 - Oct 31
Terre di Baccio
A stone building with a patio area featuring a table and chairs under a large umbrella.

3. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is ₩124,518
₩141,453 total
includes taxes & fees
Nov 29 - Nov 30
Relais Villa Olmo - Place of Charme
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

4. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (57 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ₩129,443
₩151,250 total
includes taxes & fees
Oct 30 - Oct 31
Villa San Filippo
An arched entrance with a lantern above, flanked by two potted plants.

5. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is ₩213,197
₩240,494 total
includes taxes & fees
Nov 23 - Nov 24
Villa il Fedino
A stone building with a garden in front.

6. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is ₩251,652
₩288,771 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Argenina
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

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, (92 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is ₩153,092
₩174,310 total
includes taxes & fees
Nov 2 - Nov 3
B&B La Fonte del Machiavelli
A hot tub with two glasses of a beverage.

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is ₩222,404
₩244,644 total
includes taxes & fees
Oct 30 - Oct 31
Villa di Sotto
A table with breakfast items and a view of rolling hills.

9. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is ₩115,281
₩129,763 total
includes taxes & fees
Nov 6 - Nov 7
Chianti Village Morrocco
A two-story house with a patio area, potted plants, and outdoor furniture.

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is ₩191,357
₩216,396 total
includes taxes & fees
Nov 11 - Nov 12
La Locanda di Pietracupa
A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

11. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ₩177,256
₩197,936 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Pacini
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

12. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is ₩169,033
₩191,846 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

13. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ₩174,578
₩197,945 total
includes taxes & fees
Oct 30 - Oct 31
Residenzia del Sogno
A tented room with a bed, curtains, and a view of an outdoor deck.

14. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (122 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is ₩63,453
₩74,230 total
includes taxes & fees
Oct 30 - Oct 31
hu Firenze Certosa camping in town
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

15. 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 ₩153,314
₩177,611 total
includes taxes & fees
Nov 29 - Nov 30
Casa Vacanze Squarcialupi
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

16. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is ₩140,831
₩157,130 total
includes taxes & fees
Oct 30 - Oct 31
Relais Villa Belvedere
A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

17. 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
The price is ₩122,600
₩140,837 total
includes taxes & fees
Oct 31 - Nov 1
Mariani Bed & Breakfast
A stone building with a yellow sign reading "b&b erioico".

18. 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 ₩170,161
₩198,995 total
includes taxes & fees
Nov 2 - Nov 3
L' Eroico
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

19. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (173 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 ₩100,074
₩127,807 total
includes taxes & fees
Nov 1 - Nov 2
I Parigi Corbinelli
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

20. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is ₩213,529
₩234,882 total
includes taxes & fees
Nov 3 - Nov 4
Relais Villa Belpoggio - Residenza d'Epoca
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

Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme

8/10 Good
"It was a beautiful place. Location was perfect to travel around. It was very clean. Restaurant is decent and food was good. Breakfast was ok."
Rahul 1-night trip
Posted 23 hours ago
Hotel Borgo di Cortefreda Relais - Place of Charme

Find out more about Chianti Region

Search for Vacation rentals in Chianti Region on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chianti Region using one of the methods below:

  • View our selection of featured Vacation rentals in Chianti Region
  • Use the map to find apartments and other Vacation homes in the Chianti Region neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chianti Region while they last

Look no further and take a look at our great range of rental properties in Chianti Region!

Explore a world of travel with Expedia