Chianti Region Vacation 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
Jul 19 - Jul 20
Tomorrow
Jul 20 - Jul 21
Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3

Vacation Rentals in Chianti Region

Hu Norcenni Girasole Village
Exterior

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
Aerial view

Relais Villa Olmo

9.4 out of 10, Exceptional, (212)
"Beautiful place!! For sure I will come back!! "
The price is P11,788
P13,166 total
includes taxes & fees
Jul 23 - Jul 24
Relais Villa Olmo
Camping Village Il Poggetto
Seasonal outdoor pool

Camping Village Il Poggetto

3.0 star property
8.2 out of 10, Very Good, (50)
"Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant "
The price is P4,624
P5,220 total
includes taxes & fees
Aug 18 - Aug 19
Camping Village Il Poggetto
Chianti Village Morrocco
Outdoor pool, pool umbrellas, sun loungers

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
Seasonal outdoor pool, pool umbrellas, sun loungers

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
Front of property - evening/night

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 P6,825
P7,707 total
includes taxes & fees
Aug 3 - Aug 4
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
Indoor pool, 3 outdoor pools, open 10 AM to 6 PM, pool umbrellas

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
Interior detail

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
Outdoor pool, pool umbrellas, sun loungers

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 P14,281
P15,843 total
includes taxes & fees
Aug 3 - Aug 4
Riserva di Fizzano Residence
Castello Del Nero - Podere San Filippo
Outdoor pool, pool umbrellas, sun loungers

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
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

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 P12,661
P14,126 total
includes taxes & fees
Aug 5 - Aug 6
Relais Villa Belvedere
Palazzo Pacini
Property entrance

Palazzo Pacini

9.6 out of 10, Exceptional, (89)
"Charming hotel, wonderful staff and an excellent breakfast! Highly recommended!"
The price is P10,611
P11,805 total
includes taxes & fees
Aug 15 - Aug 16
Palazzo Pacini
Rocca Palazzaccio
Full-size fridge, oven, stovetop, espresso maker

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
Outdoor pool, pool umbrellas, sun loungers

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
View from property

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 P11,183
P12,302 total
includes taxes & fees
Jul 21 - Jul 22
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

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"This is truly my favorite place in the world—peaceful, beautiful, and filled with the kindest staff. I’m so glad we found it. I didn’t want to leave and joked with my family that I might just run away and stay forever. The location and scenery are absolutely stunning. We enjoyed fantastic meals during our stay—even though the Michelin-starred restaurant wasn’t open, the other dining options were exceptional."
Ashley 1-night trip
Posted 3 days ago
Castello di Spaltenna- Small Luxury Hotels of the World