Chianti Region Holiday Rentals, Tuscany: Private House Rentals

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Our top choices for Chianti Region hotels

A narrow street with buildings on either side, a flag, and a bench.

1. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp2.223.428 total

includes taxes & fees

1 Dec - 2 Dec

A large, historic building complex with multiple structures, surrounded by lush greenery and vineyards, featuring a swimming pool.

2. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

Rp14.597.976 total

includes taxes & fees

16 Nov - 17 Nov

A dining area with a table and chairs, a view of a landscape through an arched window, and a large umbrella providing shade.

3. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

Rp5.481.855 total

includes taxes & fees

11 Nov - 12 Nov

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

4. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

Rp5.589.461 total

includes taxes & fees

16 Nov - 17 Nov

A narrow stone pathway leading to a rustic building with a wooden door and a window.

5. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

Rp3.244.447 total

includes taxes & fees

8 Nov - 9 Nov

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

6. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

Rp1.441.525 total

includes taxes & fees

9 Nov - 10 Nov

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

7. Belvedere di San Leonino

Castellina in Chianti

Kevork

Rp2.261.538 total

includes taxes & fees

12 Nov - 13 Nov

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

8. Tenuta CorteDomina

Radda in Chianti

piyanut

Rp4.351.578 total

includes taxes & fees

9 Nov - 10 Nov

A pool with a pink flamingo float, surrounded by lounge chairs and a stone deck.

9. La Pensione di Vignamaggio

Panzano in Chianti

Jacob

Rp2.870.593 total

includes taxes & fees

8 Nov - 9 Nov

A courtyard with stone flooring, arched walkways, and a central fountain.

10. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp2.193.757 total

includes taxes & fees

8 Nov - 9 Nov

A spa area with a stone ceiling, a pool, and two sun loungers.

11. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

Rp1.563.549 total

includes taxes & fees

8 Dec - 9 Dec

A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

12. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Kerry

Rp2.136.909 total

includes taxes & fees

15 Nov - 16 Nov

A pool with a view of a lush valley and distant buildings.

13. Castello Vicchiomaggio

Greve in Chianti

Danette

Rp3.827.785 total

includes taxes & fees

8 Nov - 9 Nov

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

14. Borgo Vescine

Radda in Chianti

Natalie

Rp9.371.942 total

includes taxes & fees

17 Nov - 18 Nov

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

15. Castello La Leccia

Castellina in Chianti

Susan

Rp3.065.069 total

includes taxes & fees

13 Nov - 14 Nov

A person sitting by a swimming pool with a stone building in the background.

16. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Rahul

Rp1.848.603 total

includes taxes & fees

29 Nov - 30 Nov

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

17. Terre di Baccio

Greve in Chianti

Gage

Rp5.226.696 total

includes taxes & fees

10 Nov - 11 Nov

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

18. The Club House

Castelnuovo Berardenga

Natalyn

Rp9.229.340 total

includes taxes & fees

14 Nov - 15 Nov

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

19. Villa San Lucchese

Poggibonsi

James

Rp2.072.507 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

20. Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Elsa

Rp1.442.661 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Compare top hotels in Chianti Region

Palazzo Leopoldo Dimora Storica & Spa 4.0 star property Radda in Chianti View	COMO Castello Del Nero 5.0 star property Tavarnelle Val di Pesa View	Chapter Chianti, a Member of Design Hotels 5.0 star property Cavriglia View	Dievole Wine Resort Castelnuovo Berardenga View	Castello di Fonterutoli Wine Resort Castellina in Chianti View
9.2 Wonderful 305 reviews	9.6 Exceptional 146 reviews	8.4 Very good 23 reviews	9.6 Exceptional 219 reviews	9.4 Exceptional 234 reviews
The price is Rp1.911.350 Rp2.223.428 total includes taxes & fees 1 Dec - 2 Dec	The price is Rp13.123.228 Rp14.597.976 total includes taxes & fees 16 Nov - 17 Nov	The price is Rp4.872.760 Rp5.481.855 total includes taxes & fees 11 Nov - 12 Nov	The price is Rp4.933.669 Rp5.589.461 total includes taxes & fees 16 Nov - 17 Nov	The price is Rp2.875.667 Rp3.244.447 total includes taxes & fees 8 Nov - 9 Nov
No Breakfast included Yes, Pool Yes, Spa Yes, Pet-friendly Yes, WiFi included Yes, Parking	Yes, Breakfast included Yes, Pool Yes, Spa Yes, Pet-friendly Yes, WiFi included Yes, Parking	Yes, Breakfast included Yes, Pool Yes, Spa Yes, Pet-friendly Yes, WiFi included Yes, Parking	Yes, Breakfast included Yes, Pool No Spa No Pet-friendly Yes, WiFi included Yes, Parking	No Breakfast included No Pool No Spa Yes, Pet-friendly Yes, WiFi included No Parking

Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the churches and wineries in this walkable area.

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Learn more about Chianti Region

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

See all hotels in Chianti Region

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Castello La Leccia

Castellina in Chianti

10/10 Excellent

Iain

A covered patio with wooden tables and chairs, large windows, and a view of the garden.

Albergo Villa San Michele

Greve in Chianti

10/10 Excellent

This was an amazing stay and definitely one of our favourite places we stayed in Tuscany. The room was spacious, comfortable, and beautifully presented, and the whole property was absolutely beautiful. Alice and Daniele, who run the place, were amazing hosts. They were so welcoming and helpful, and the service throughout our stay was excellent. We absolutely loved our time here and would happily stay again!

Sharon

An aerial view of a large estate with a swimming pool, tennis courts, and a vineyard.

The Club House

Castelnuovo Berardenga

10/10 Excellent

A wonderful stay at The Club House. This is a gorgeous place in a beautiful setting in the heart of Chianti. The property is immaculate, the staff friendly and the food delicious. We have been to wonderful hotels all over the world but this place is really special. It was our second visit (we stayed in August 2025). Everything was great but if I had to be picky I would say the gym is insanely hot in the morning (despite asking for the air con to be put on the evening before). Also, having...

Elizabeth

A villa with a swimming pool, surrounded by well-maintained gardens and tall trees.

Villa La Cappella

Montespertoli

10/10 Excellent

Our stay at Villa La Capella was nothing short of perfect. The two owners, Paula and Anthony, were both such incredible individuals. I have never experienced anything so warm and welcoming during my travels. The hospitality they provided went above and beyond what anyone would expect or could ask for. My partner and I will be returning again and again, if not for the most gorgeous views of the country side (or the beautiful and elegant Kobe, one of three resident dogs that live there) but for...

ADAM

A poolside area with lounge chairs and a large pool, surrounded by well-manicured lawns and tall cypress trees.

One Belvedere Tuscany

Poggibonsi

10/10 Excellent

Such a wonderful long weekend at the belvedere. The property is absolutely beautiful, the location, grounds and view are something to be seen, and the staff very friendly and accommodating. We had not rented a car, and they went above and beyond to assist us with getting around and enjoying events planned on site. Everything felt luxurious, and my partner and I felt more relaxed than we have on any other holiday this year! Recommend to any couple looking for a quiet, romantic trip!

Nicola

A cozy living room with large windows, a dining area, and a kitchen.

Torraccia di Chiusi

San Gimignano

10/10 Excellent

After the drive from Pisa airport, the drive up the 4km track led to a most stunning property. We were immediately welcomed by Stefano (and two cold beers!) and the hospitality continued throughout our stay. The five course Tuscan dinner every evening was worth every cent and how amazing were the team in making sure everything was perfect?! The pool was beautiful with stunning views. Truly an incredible location, breakfast, hosts, staff and home-grown, home-made food and drink. Thank you for...

David

A narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.

Hotel Il Castello

Certaldo Alto

10/10 Excellent

Staying at Hotel Il Castello was a step back into history - a beautiful appointed historic building that had been sympathetically made over into a hotel/bar/restaurant, with panoramic views over Lower Certaldo. The bedrooms very clean, with rustic charm and furnishings. Modern functioning shower, TV, and AIRCON unit which was very welcome in the intensive 30+ degree heat of the day and night. The background music in the restaurant/bar always playing Jazz music - which, whilst not my favourite...

peter

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Jess

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Yoke yin

Find hotels in Chianti Region from Rp1.032.138

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chianti Region

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Chianti Region hotels

1. Palazzo Leopoldo Dimora Storica & Spa

2. COMO Castello Del Nero

3. Chapter Chianti, a Member of Design Hotels

4. Dievole Wine Resort

5. Castello di Fonterutoli Wine Resort

6. La Certosa di Pontignano - Place of Charme

7. Belvedere di San Leonino

8. Tenuta CorteDomina

9. La Pensione di Vignamaggio

10. Villa Casagrande Resort & SPA

11. Hotel Palazzo San niccolò & Spa

12. Hotel Palazzo San Lorenzo & SPA

13. Castello Vicchiomaggio

14. Borgo Vescine

15. Castello La Leccia

16. Hotel Borgo di Cortefreda Relais - Place of Charme

17. Terre di Baccio

18. The Club House

19. Villa San Lucchese

20. Salvadonica - Borgo del Chianti

Compare top hotels in Chianti Region

Palazzo Leopoldo Dimora Storica & Spa

COMO Castello Del Nero

Chapter Chianti, a Member of Design Hotels

Dievole Wine Resort

Castello di Fonterutoli Wine Resort

Stay near popular Chianti Region attractions

Antinori nel Chianti Classico

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Castello La Leccia

10/10 Excellent