Chianti Region Holiday Rentals, Tuscany: Private House Rentals

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Our top choices for Chianti Region hotels

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

1. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

Rp5.495.013 total

includes taxes & fees

8 Nov - 9 Nov

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

2. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

Rp5.602.878 total

includes taxes & fees

16 Nov - 17 Nov

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

3. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp3.419.119 total

includes taxes & fees

6 Nov - 7 Nov

An aerial view of a historic estate with multiple buildings, a swimming pool, and terraced vineyards.

4. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

Rp14.633.016 total

includes taxes & fees

16 Nov - 17 Nov

A spa area with stone walls, a white massage chair, and a potted plant.

5. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp2.195.913 total

includes taxes & fees

23 Nov - 24 Nov

A rustic stone wall with a window, a potted plant, a bust sculpture, and a table with a magazine.

6. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp4.362.023 total

includes taxes & fees

9 Nov - 10 Nov

A stone building with a tiled roof, green shutters, and a small staircase leading to a door.

7. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

Rp3.445.576 total

includes taxes & fees

8 Nov - 9 Nov

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

8. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

Rp8.502.454 total

includes taxes & fees

6 Nov - 7 Nov

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

9. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

Rp1.578.656 total

includes taxes & fees

1 Dec - 2 Dec

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

10. Belvedere di San Leonino

Castellina in Chianti

Kevork

Rp2.266.965 total

includes taxes & fees

11 Nov - 12 Nov

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

11. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Rahul

Rp1.836.556 total

includes taxes & fees

29 Nov - 30 Nov

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

12. La Pensione di Vignamaggio

Panzano in Chianti

Jacob

Rp2.877.358 total

includes taxes & fees

6 Nov - 7 Nov

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

13. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp2.199.023 total

includes taxes & fees

8 Nov - 9 Nov

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

14. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

Rp4.622.934 total

includes taxes & fees

6 Nov - 7 Nov

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

15. Castello La Leccia

Castellina in Chianti

Susan

Rp3.516.147 total

includes taxes & fees

11 Nov - 12 Nov

A swimming pool, steps, and a grassy area with umbrellas.

16. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp2.142.038 total

includes taxes & fees

8 Nov - 9 Nov

A cozy room with a wooden floor, a sofa, a table with a glass, and a view through a window.

17. Villa Barberino

Meleto

Claire

Rp3.428.850 total

includes taxes & fees

7 Nov - 8 Nov

An aerial view of a rustic village with stone buildings, a central courtyard with string lights, and a swimming pool.

18. Borgo Vescine

Radda in Chianti

Natalie

Rp9.394.436 total

includes taxes & fees

17 Nov - 18 Nov

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.

19. Terre di Baccio

Greve in Chianti

Gage

Rp5.277.202 total

includes taxes & fees

6 Nov - 7 Nov

A yellow building with stone pillars, multiple windows, and a statue in the garden.

20. Villa San Lucchese

Poggibonsi

James

Rp2.070.520 total

includes taxes & fees

29 Nov - 30 Nov

View all properties

Compare top hotels in Chianti Region

Chapter Chianti, a Member of Design Hotels 5.0 star property Cavriglia View	Dievole Wine Resort Castelnuovo Berardenga View	Hotel Villa Campomaggio 4.0 star property Radda in Chianti View	COMO Castello Del Nero 5.0 star property Tavarnelle Val di Pesa View	Palazzo Leopoldo Dimora Storica & Spa 4.0 star property Radda in Chianti View
8.4 Very good 23 reviews	9.6 Exceptional 219 reviews	9.4 Exceptional 196 reviews	9.6 Exceptional 146 reviews	9.2 Wonderful 305 reviews
The price is Rp4.884.456 Rp5.495.013 total includes taxes & fees 8 Nov - 9 Nov	The price is Rp4.945.512 Rp5.602.878 total includes taxes & fees 16 Nov - 17 Nov	The price is Rp2.997.280 Rp3.419.119 total includes taxes & fees 6 Nov - 7 Nov	The price is Rp13.154.728 Rp14.633.016 total includes taxes & fees 16 Nov - 17 Nov	The price is Rp1.885.274 Rp2.195.913 total includes taxes & fees 23 Nov - 24 Nov
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 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	No Breakfast included Yes, Pool Yes, Spa Yes, Pet-friendly Yes, WiFi included Yes, 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 stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

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 rustic stone building with a tiled roof, surrounded by a wooden fence and tall trees.

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

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

An outdoor dining area with tables and chairs, a brick wall, and a view of the landscape.

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

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Yoke yin

Find hotels in Chianti Region from Rp1.012.414

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chianti Region

Check prices for these dates

Filter by

Property class

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Our top choices for Chianti Region hotels

1. Chapter Chianti, a Member of Design Hotels

2. Dievole Wine Resort

3. Hotel Villa Campomaggio

4. COMO Castello Del Nero

5. Palazzo Leopoldo Dimora Storica & Spa

6. Tenuta CorteDomina

7. Castello di Fonterutoli Wine Resort

8. Borgo Scopeto Wine & Country Relais

9. Hotel Palazzo San niccolò & Spa

10. Belvedere di San Leonino

11. Hotel Borgo di Cortefreda Relais - Place of Charme

12. La Pensione di Vignamaggio

13. Villa Casagrande Resort & SPA

14. Castello Vicchiomaggio

15. Castello La Leccia

16. Hotel Palazzo San Lorenzo & SPA

17. Villa Barberino

18. Borgo Vescine

19. Terre di Baccio

20. Villa San Lucchese

Compare top hotels in Chianti Region

Chapter Chianti, a Member of Design Hotels

Dievole Wine Resort

Hotel Villa Campomaggio

COMO Castello Del Nero

Palazzo Leopoldo Dimora Storica & Spa

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