Chianti Region Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
15 Jul - 16 Jul
Tomorrow
16 Jul - 17 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Chianti Region

Hu Norcenni Girasole Village
Enjoy a sea view from the covered porch of this cabin, which features a dining area with a table and chairs.

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (298)
"I would definitely recommend and would go back in a heartbeat "
Hu Norcenni Girasole Village
Relais Villa Olmo
Escape to a serene villa surrounded by lush greenery and a tranquil pool.

Relais Villa Olmo

9.4 out of 10, Exceptional, (212)
"Beautiful place!! For sure I will come back!! "
The price is S$355
includes taxes & fees
27 Jul - 28 Jul
Relais Villa Olmo
Camping Village Il Poggetto
Relax by the serene pool surrounded by lush greenery and palm trees.

Camping Village Il Poggetto

3.0 star property
8.0 out of 10, Very good, (49)
"Beautiful Tuscan countryside "
The price is S$95
includes taxes & fees
16 Jul - 17 Jul
Camping Village Il Poggetto
Chianti Village Morrocco
Relax by the pool surrounded by a white picket fence.

Chianti Village Morrocco

3.0 star property
8.6 out of 10, Excellent, (101)
"Nothing wrong here! Fantastic, professional staff that took care of all our needs and always went the extra mile. Fantastic chef with great food and lovely “can help” attitude. Prestine pool! Would book again"
Chianti Village Morrocco
Villa San Filippo
Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

Villa San Filippo

4.0 star property
8.4 out of 10, Very good, (39)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
Villa San Filippo
Villa Il Palagio
Relax by the serene pool surrounded by lush greenery and a tranquil atmosphere.

Villa Il Palagio

8.6 out of 10, Excellent, (56)
"We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great"
The price is S$137
includes taxes & fees
22 Jul - 23 Jul
Villa Il Palagio
Relais Badia a Passignano
Seasonal outdoor pool

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Villa Norcenni Aparthotel
Guests can enjoy a refreshing swim in the pool surrounded by lush greenery and a soothing water feature.

Villa Norcenni Aparthotel

2.0 star property
7.4 out of 10, Good, (20)
"It was clean and safe."
Villa Norcenni Aparthotel
Castello di Montegufoni
Experience the grandeur of this beautifully decorated room, featuring intricate frescoes, plush seating, and classical artwork.

Castello di Montegufoni

8.2 out of 10, Very good, (28)
"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "
Castello di Montegufoni
Riserva di Fizzano Residence
Relax by the serene pool surrounded by lush green hills and steps leading into the water.

Riserva di Fizzano Residence

3.0 star property
9.8 out of 10, Exceptional, (20)
"We absolutely loved this hotel. The views were incredible and the dinner we had in the restaurant was amazing. The apartments are spacious and have everything you need except maybe some hair conditioner. The breakfast wasn’t the best I’ve ever had but fine with a decent selection. The staff are all super friendly and helpful. "
The price is S$356
includes taxes & fees
3 Aug - 4 Aug
Riserva di Fizzano Residence
Castello Del Nero - Podere San Filippo
Relax by the pool with a clear view of the surrounding landscape, surrounded by six lounge chairs and umbrellas.

Castello Del Nero - Podere San Filippo

10.0 out of 10, Exceptional, (37)
"Beautiful property and surrounds. Room was exactly as described, highly recommended "
Castello Del Nero - Podere San Filippo
Relais Villa Belvedere
Relax by the serene pool, surrounded by lush views and comfortable seating.

Relais Villa Belvedere

9.2 out of 10, Wonderful, (67)
"Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer."
The price is S$305
includes taxes & fees
5 Aug - 6 Aug
Relais Villa Belvedere
Palazzo Pacini
Enter the elegant PALAZZO PACINI, where a grand arched doorway welcomes guests.

Palazzo Pacini

9.6 out of 10, Exceptional, (88)
"Very charming Tuscan feel and Great hospitality, we felt very welcome!"
The price is S$261
includes taxes & fees
16 Jul - 17 Jul
Palazzo Pacini
Rocca Palazzaccio
Cozy living space with a sofa, kitchen, and TV, offering a view of the outdoors.

Rocca Palazzaccio

3.0 star property
9.0 out of 10, Wonderful, (13)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
Rocca Palazzaccio
Podere il Pino
Relax by the serene pool surrounded by lush greenery and trees, with lounge chairs and umbrellas at your disposal.

Podere il Pino

9.4 out of 10, Exceptional, (16)
"Beautiful place to stay. Great for kids and has an amazing view. "
Podere il Pino
Relais Villa Belpoggio - Residenza d'Epoca
Traditional building with a central arched entrance and stone pillars, set amidst mature trees and a shaded entrance area.

Relais Villa Belpoggio - Residenza d'Epoca

9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
The price is S$277
includes taxes & fees
27 Jul - 28 Jul
Relais Villa Belpoggio - Residenza d'Epoca
Borgo Argenina
Terrace/patio

Borgo Argenina

9.8 out of 10, Exceptional, (21)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
Borgo Argenina
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
Sign in
Sign up, it's free