Cavallari Holiday Rentals, Castellina in Chianti: Private House Rentals

Q: What are some of the best holiday rentals that Cavallari has to offer?

Borgo Argiano : This holiday home rental outside of Cavallari is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in Cavallari .

Q: What are some hotels with pools in Cavallari?

Radisson Blu Hotel, Florence : Hotel located near Ponte Vecchio. Features free self parking, an outdoor pool and a 24-hour fitness centre. Poderi Arcangelo and Fattoria di Vegi are a couple of other choices that feature an on-site pool. View all hotels with pools in Cavallari .

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Our top choices for Cavallari hotels

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

1. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

Rp5.722.893 total

includes taxes & fees

16 Nov - 17 Nov

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

2. Borgo Vescine

Radda in Chianti

Natalie

Rp9.291.901 total

includes taxes & fees

22 Nov - 23 Nov

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

3. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

Rp14.473.304 total

includes taxes & fees

20 Nov - 21 Nov

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

4. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

Rp3.216.737 total

includes taxes & fees

15 Nov - 16 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

Rp2.220.522 total

includes taxes & fees

13 Dec - 14 Dec

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

6. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

Rp1.561.426 total

includes taxes & fees

1 Dec - 2 Dec

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

Rp2.242.255 total

includes taxes & fees

21 Nov - 22 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

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.

9. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

Rp1.537.914 total

includes taxes & fees

16 Nov - 17 Nov

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

10. Villa San Lucchese

Poggibonsi

James

Rp1.892.480 total

includes taxes & fees

29 Nov - 30 Nov

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

11. Hotel Villa San Giorgio

Poggibonsi

Arik

Rp1.087.008 total

includes taxes & fees

13 Dec - 14 Dec

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

12. Hotel Casafrassi

Castellina in Chianti

Stuart

Rp1.308.435 total

includes taxes & fees

26 Nov - 27 Nov

A person sitting in a corner of a room with tiled walls and a bench.

13. Hotel Il Piccolo Castello

Monteriggioni

Frank

Rp2.350.553 total

includes taxes & fees

15 Nov - 16 Nov

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

14. Hotel Ristorante La Dama nella Vigna

Monteriggioni

Amanda

Rp2.151.470 total

includes taxes & fees

10 Dec - 11 Dec

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

15. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

Rp7.649.313 total

includes taxes & fees

14 Nov - 15 Nov

A rock garden with various succulents and plants.

16. Hotel Toscana Ambassador

Poggibonsi

Marian

Rp1.222.883 total

includes taxes & fees

20 Nov - 21 Nov

A dining area with wooden furniture, a chandelier, and potted plants.

17. Albergo Il Colombaio

Castellina in Chianti

Christine

Rp3.079.855 total

includes taxes & fees

16 Nov - 17 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

Rp9.216.818 total

includes taxes & fees

19 Nov - 20 Nov

A sunset scene with a person holding a child, benches, and umbrellas in a park setting.

19. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Rahul

Rp1.736.847 total

includes taxes & fees

8 Dec - 9 Dec

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

20. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Kerry

Rp2.118.657 total

includes taxes & fees

15 Nov - 16 Nov

View all properties

Top Cavallari Hotel Reviews

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Jess

Borgo Vescine

Radda in Chianti

10/10 Excellent

I'd never heard of Radda before but this place is a gem, just outside of this little Tuscan town. Situated near In Greve, Castellina, and the Chianti road, the service, sights, and grounds are unbelievable. I travelled to this hotel with my parents and we each staying in rooms that felt like separate villas. Theirs had an amazing view and mine had a private porch that was tucked away, perfect for sitting with friends or family to have a late night glassw of wine or cigar. The grounds feel very...

Matt

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Yoke yin

Villa San Lucchese

Poggibonsi

10/10 Excellent

Anonymous traveller

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

10/10 Excellent

Anonymous traveller

Hotel Ristorante La Dama nella Vigna

Monteriggioni

10/10 Excellent

Ryan

Castello di Fonterutoli Wine Resort

Castellina in Chianti

10/10 Excellent

Claire

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

This place is surreal. We felt like we were on the set of the Name of the Rose. Sleeping in a real XIV century monastery, with its own church (with amazing frescoes), on a hill overlooking the grapes and olive trees dotted countryside...just unbelievable. We stay in one the celle, which is a 3 bedroom apartment on 2 floors, with your own private garden...yes, that's correct. Simply unheard of. The location is great too (Siena is a short drive away). The only setbacks were breakfast, very...

Ivo

Hotel Il Piccolo Castello

Monteriggioni

10/10 Excellent

Vinay

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Excellent

Charles

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 swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

Sangallo Park Hotel

Vico Alto

10/10 Excellent

I was one of a party of four adults who have just returned from a wonderful and relaxing seven day holiday at the Sangallo Park Hotel which is in close proximity to Siena ( less than 10 minutes in a Car). On arrival we were greeted by a very friendly gentleman on reception who give us an overview of the hotel and provided us with details of a local restaurant as it was late at night, he even rang the restaurant straight away and booked us a table. Every morning we were greeted by...

Brian, Julie

Hotel Casafrassi

Castellina in Chianti

10/10 Excellent

Stuart

Frequently Asked Questions

What are some of the best holiday rentals that Cavallari has to offer?

Borgo Argiano: This holiday home rental outside of Cavallari is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in Cavallari.

If I need to cancel my hotel reservation in Cavallari, will I receive a refund?

Yes, the majority of hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cavallari.

What are some hotels with pools in Cavallari?

Radisson Blu Hotel, Florence: Hotel located near Ponte Vecchio. Features free self parking, an outdoor pool and a 24-hour fitness centre. Poderi Arcangelo and Fattoria di Vegi are a couple of other choices that feature an on-site pool. View all hotels with pools in Cavallari.

What is staying in Cavallari like?

Those travelling to Cavallari will definitely enjoy the sights to see and things to do. In Cavallari, there are 6 hotels and other accommodation options to choose from. Find out more about Cavallari.

What are the top places to visit in Cavallari?

Places to visit in the wider area include City Hall Castellina In Chianti, Il Molino di Grace Winery and Borgo di Vescine - Tenute di Castelvecchi. You'll also find Castello di Radda Winery and Isole e Olena Winery in the area. Take a look at what more there is to see and do in Expedia's Cavallari guide.

What's the seasonal weather in Cavallari?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Cavallari is 946 mm.

Where is the best place to stay in Cavallari?

Located 18.1 mi (29.1 km) from the heart of Cavallari, Radisson Blu Hotel, Florence is a top choice for your stay, based on our traveller data. Other good options for your trip to the area are La Certosa di Pontignano and Hotel Athena. See all available top hotels, or vacation rentals in Cavallari.

Find hotels in Cavallari from Rp816.902

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cavallari

Check prices for these dates

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Property class

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Our top choices for Cavallari hotels

1. Dievole Wine Resort

2. Borgo Vescine

3. COMO Castello Del Nero

4. Castello di Fonterutoli Wine Resort

5. Palazzo Leopoldo Dimora Storica & Spa

6. Hotel Palazzo San niccolò & Spa

7. Belvedere di San Leonino

8. Tenuta CorteDomina

9. La Certosa di Pontignano - Place of Charme

10. Villa San Lucchese

11. Hotel Villa San Giorgio

12. Hotel Casafrassi

13. Hotel Il Piccolo Castello

14. Hotel Ristorante La Dama nella Vigna

15. Chapter Chianti, a Member of Design Hotels

16. Hotel Toscana Ambassador

17. Albergo Il Colombaio

18. The Club House

19. Hotel Borgo di Cortefreda Relais - Place of Charme

20. Hotel Palazzo San Lorenzo & SPA

Top Cavallari Hotel Reviews

Belvedere di San Leonino

10/10 Excellent

Frequently Asked Questions

What are some of the best holiday rentals that Cavallari has to offer?

If I need to cancel my hotel reservation in Cavallari, will I receive a refund?

What are some hotels with pools in Cavallari?

What is staying in Cavallari like?

What are the top places to visit in Cavallari?

What's the seasonal weather in Cavallari?

Where is the best place to stay in Cavallari?