San Leonino Holiday Rentals, Castellina in Chianti: Private House Rentals

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Our top choices for San Leonino hotels

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Castellina in Chianti

Baby high chair

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.

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

A rustic stone building with a garden in front.

A person relaxing in a hot tub with a view of a building and trees in the background.

1. Belvedere di San Leonino

Castellina in Chianti

Jess

Rp2.044.222

Rp2.372.562 total

includes taxes & fees

21 Sept - 22 Sept

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

A dining area with a table set for two, featuring wine bottles and bread.

A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

2. Castello La Leccia

Castellina in Chianti

Samuel

Rp5.670.865

Rp6.320.604 total

includes taxes & fees

11 Sept - 12 Sept

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

A courtyard with wicker furniture, a building with multiple windows and arches, and well-maintained greenery.

A hotel room with a bed, a desk, a chair, a window with curtains, a lamp, and a view of the landscape.

A dining area with checkered flooring, tables set with white tablecloths, and wicker chairs.

3. Palazzo Ravizza

Siena Historical Center

Kathleen

Rp2.688.110

Rp3.060.238 total

includes taxes & fees

26 Aug - 27 Aug

An outdoor patio with tables and chairs, surrounded by potted plants and a red building.

A brick building with three windows, a round blue window, and a sign on the wall.

A rustic interior with a fireplace, wooden beams, and a metal rack holding various tools.

A swimming pool with a clear view of the water, a metal structure on the right, and a landscaped area with chairs and plants in the background.

4. Borgo Grondaie

Siena

Simon

Rp2.817.955

Rp3.203.067 total

includes taxes & fees

3 Sept - 4 Sept

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.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

An interior corridor with arches, columns, and a brick wall.

5. La Certosa di Pontignano

Castelnuovo Berardenga

Edyta

Rp1.251.274

Rp1.541.709 total

includes taxes & fees

8 Sept - 9 Sept

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A modern interior with a bar area, seating, and a staircase.

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

6. Locanda le Piazze

Castellina in Chianti

Oluwafunmilayo

Rp6.762.541

Rp7.562.775 total

includes taxes & fees

29 Aug - 30 Aug

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

A balcony with two chairs and a table, overlooking a building with a tiled roof and shutters.

A modern hotel room with a large bed, a desk, and a chair. There is a painting on the wall and a lamp on the side table.

A dining area with brick ceiling arches, tables set with white tablecloths, and framed pictures on the walls.

7. Hotel Chiusarelli

Siena City Centre

sharon

Rp2.389.431

Rp2.731.691 total

includes taxes & fees

30 Aug - 31 Aug

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

8. Four Points by Sheraton Siena

Scacciapensieri

Raul

Rp2.688.110

Rp3.060.238 total

includes taxes & fees

27 Aug - 28 Aug

A rock garden with various succulents and plants.

A modern hotel lobby with a curved reception desk, seating areas, and large windows.

A modern building with the sign "Toscana Ambassador Hotel".

A modern bedroom with a large bed, a nightstand, a chair, and a TV.

9. Hotel Toscana Ambassador

Poggibonsi

Shalayna

Rp1.217.257

Rp1.462.963 total

includes taxes & fees

26 Aug - 27 Aug

A courtyard with a lemon tree, potted plants, and a building with arched windows.

A swimming pool surrounded by lush greenery and a stone pathway.

A room with a large window offering a view of a landscaped garden with trees and a pathway.

A large, historic building with a covered patio and a well-maintained garden.

10. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

Rp4.412.558

Rp4.957.131 total

includes taxes & fees

30 Aug - 31 Aug

A balcony with a table set for breakfast overlooking a historic cityscape with domed buildings and terraced houses.

A hotel room with a bed, a desk, a television, and a view of the city through large windows.

A spacious lobby with a modern design, featuring a seating area with black leather sofas and ottomans, a reception desk, and a visible kitchen area in the background.

A breakfast table with various food items and drinks, including a pitcher of juice, a glass of milk, and a plate of toast.

11. Hotel Minerva

Siena City Centre

Chia lin

Rp2.011.781

Rp2.316.358 total

includes taxes & fees

28 Aug - 29 Aug

An outdoor dining area with wicker furniture, a table set with croissants, a bowl of fruit, and a glass of orange juice.

A church interior with wooden pews, a wooden altar, and a large painting on the wall.

A neatly arranged hotel room with a large bed, bedside lamps, a mirror, and framed pictures on the wall.

A dining table with cups, plates, and a croissant, set against a window with curtains.

12. Il Chiostro del Carmine

Siena Historical Center

Isabelle

Rp1.825.886

Rp2.091.128 total

includes taxes & fees

24 Aug - 25 Aug

A table set for breakfast with a scenic view of hills and a cloudy sky.

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

13. Palazzo di Valli

Siena

Payton

Rp2.620.484

Rp2.985.850 total

includes taxes & fees

23 Aug - 24 Aug

A pool area with lounge chairs and umbrellas, surrounded by greenery and buildings.

A man and a woman in a restaurant with a stone wall and a wooden table.

A table set outdoors with wine glasses and cutlery, surrounded by greenery and trees.

A dining table with wine bottles and glasses, a menu, and a wooden box.

14. Hotel Sovestro

San Gimignano

Manuel

Rp3.634.678

Rp4.122.125 total

includes taxes & fees

28 Aug - 29 Aug

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

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

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

A room with a view of a forest through a window, a table with a lamp, and a chair.

15. Dievole Wine Resort

Castelnuovo Berardenga

Nicole

Rp5.765.066

Rp6.506.879 total

includes taxes & fees

26 Aug - 27 Aug

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A clear blue pool with lounge chairs and a stone building in the background.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

A stone building with a wooden bench outside.

16. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Scott

Rp2.031.298

Rp2.296.418 total

includes taxes & fees

20 Sept - 21 Sept

A bathroom with a window view of a historic building and a tiled roof.

A historic building with a prominent tower and arched windows, situated in a town with traditional architecture and a clear blue sky.

An outdoor patio with tables and chairs, surrounded by planters and umbrellas.

A bedroom with a large bed, a mirror, and a painting on the wall.

17. Siena Vip

Siena City Centre

Luis

Rp2.159.600

Rp2.458.504 total

includes taxes & fees

23 Aug - 24 Aug

A grand entrance with a staircase leading to a white building, surrounded by lush greenery and potted plants.

A lobby with a reception desk, a large painting, a potted plant, and a patterned floor.

A rooftop terrace with outdoor seating, including a white sofa and wicker chairs, surrounded by potted plants and overlooking a cityscape.

A swimming pool with a wooden deck, lounge chairs, and umbrellas.

18. Villa Ermellina Siena, a Tribute Portfolio Hotel

Camollia

Katherine

Rp3.418.840

Rp3.864.041 total

includes taxes & fees

27 Aug - 28 Aug

A hotel entrance with a reception area, glass doors, and a sign above reading "Hotel i Platani".

A garden area with potted plants and a fence.

A hotel room with a bed, a bedside table with a cup and a small plate, a wall-mounted heater, and a window with yellow curtains.

A hotel lobby with a reception desk, a dining area with tables and chairs, and potted plants.

19. Hotel I Platani

Monteriggioni

Jorge

Rp1.364.274

Rp1.604.018 total

includes taxes & fees

25 Aug - 26 Aug

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

A room with a sofa, a desk, a bunk bed, and a patterned floor.

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

A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.

20. Villa San Lucchese

Poggibonsi

Simona

Rp2.661.736

Rp3.051.889 total

includes taxes & fees

9 Sept - 10 Sept

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Top San Leonino Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"Antonio and the hotel staff were amazing—offering wonderful, warm hospitality. It is a new hotel set on a stunning property. It was a stay that undoubtedly leaves a lasting mark on your soul and leaves you wanting to come back to see the continuation of Antonio’s creations on the estate."

Hotel Le Fontanelle

10/10 Excellent

"Get away from it all at Hotel Le Fontanelle - Relax and Dine like the queen you are. Amazing staff, food, and unforgettable views - wish I was there right now."

Hotel Chiusarelli

10/10 Excellent

"The staff were very helpful with my questions. I had a room on the lower floor during a heat wave and the room stayed cool. The bathroom was clean and there was even a nice little balcony."

Hotel Borgo San Luigi

10/10 Excellent

"Fabulous family friendly property in Tuscany. Easy to get to many different towns. Staff were very helpful and lots of space!"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"

Villa Casagrande Resort & SPA

10/10 Excellent

"A beautiful hotel in a lovely little town. The staff were amazing, so helpful. The rooms were very clean and comfortable. I didn’t use the indoor pool or spa facilities so can’t comment on them. The outdoor pool is across the road and up a steep hill, so great if you have a car but not so much if you are on foot! Overall a very good stay."

Hotel Athena

10/10 Excellent

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

La Certosa di Pontignano

10/10 Excellent

"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."

More cheap stays in San Leonino

Cannon d'Oro

Via Montanini 28 Siena SI

Rp1.475.682

Rp1.726.930 total

23 Aug - 24 Aug

includes taxes & fees

7.8/10 Good! (258 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

Rp1.670.348

Rp1.940.700 total

23 Aug - 24 Aug

includes taxes & fees

10/10 Exceptional! (48 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

Rp1.735.719

Rp2.012.608 total

23 Aug - 24 Aug

includes taxes & fees

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

Rp1.749.807

Rp2.028.105 total

23 Aug - 24 Aug

includes taxes & fees

8.8/10 Excellent! (104 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

Rp1.590.094

Rp3.464.158 total

24 Aug - 25 Aug

includes taxes & fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

Frequently asked questions

Where is the best place to stay in San Leonino?

Located 7.4 mi (11.9 km) from the heart of San Leonino, Hotel Athena is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Grand Hotel Continental Siena – Starhotels Collezione and Borgo Scopeto Wine & Country Relais. See all available top hotels, or vacation rentals in San Leonino.

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

Borgo Argiano: This holiday home rental outside of San Leonino 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 an espresso maker. You can relax into your holiday with a garden and a library. See all vacation rentals in San Leonino.

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

Yes! Most hotel room reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in San Leonino.

How is it staying in San Leonino?

Those travelling to San Leonino will definitely enjoy the sights to see and things to do. In San Leonino, there are 2 hotels and other accommodation options to choose from. Find out more about San Leonino.

What is there to see in San Leonino?

Places to visit in the wider area include City Hall Castellina In Chianti, Terra di Seta and Castello di Radda Winery. You'll also find Meleto Castle and Isole e Olena Winery in the area. Take a look at what more there is to see and do in Expedia's San Leonino guide.

What's the seasonal weather like in San Leonino?

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 San Leonino is 944 mm.

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Find hotels in San Leonino from Rp1.462.963

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leonino

Check prices for these dates

Filter by

Star rating

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Our top choices for San Leonino hotels

1. Belvedere di San Leonino

2. Castello La Leccia

3. Palazzo Ravizza

4. Borgo Grondaie

5. La Certosa di Pontignano

6. Locanda le Piazze

7. Hotel Chiusarelli

8. Four Points by Sheraton Siena

9. Hotel Toscana Ambassador

10. Villa Scacciapensieri Boutique Hotel

11. Hotel Minerva

12. Il Chiostro del Carmine

13. Palazzo di Valli

14. Hotel Sovestro

15. Dievole Wine Resort

16. Hotel Colle Etrusco Salivolpi

17. Siena Vip

18. Villa Ermellina Siena, a Tribute Portfolio Hotel

19. Hotel I Platani

20. Villa San Lucchese

Top San Leonino Hotel Reviews

Fattoria di Vegi

Hotel Le Fontanelle

Hotel Chiusarelli

Hotel Borgo San Luigi

Grand Hotel Continental Siena – Starhotels Collezione

Villa Casagrande Resort & SPA

Hotel Athena

Borgo Scopeto Wine & Country Relais

La Certosa di Pontignano

More cheap stays in San Leonino

Cannon d'Oro

Torre del Fuggisole

Piccolo Hotel Etruria

Albergo Centrale

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

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