𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 San Leonino (2026)

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Our top choices for San Leonino hotels

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 poolside area with lounge chairs and a view of the night sky.

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

A rustic stone building with a garden in front.

1. Belvedere di San Leonino

Castellina in Chianti

Seong Won

S$186

includes taxes & fees

7 Oct - 8 Oct

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

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

2. Hotel Casafrassi

Castellina in Chianti

Jane

S$96

includes taxes & fees

20 Sept - 21 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 bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

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

3. Castello La Leccia

Castellina in Chianti

Samuel

S$456

includes taxes & fees

9 Oct - 10 Oct

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

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

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

4. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

S$186

includes taxes & fees

13 Oct - 14 Oct

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 living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

A stone building with a wooden bench outside.

5. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

S$157

includes taxes & fees

20 Sept - 21 Sept

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

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

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

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

6. Dievole Wine Resort

Castelnuovo Berardenga

Karamjit

S$456

includes taxes & fees

14 Oct - 15 Oct

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A stone building with a window and a light fixture.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

7. Agriturismo San Sano

Gaiole in Chianti

Ernesto

S$119

includes taxes & fees

14 Oct - 15 Oct

A pathway lined with trees and a large pot in the center.

A bedroom with a bed, bedside lamps, a wooden table, and a balcony with a view of greenery.

A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.

A breakfast buffet with pastries and a coffee machine.

8. Villa Montarioso

Montarioso

Michael

S$122

includes taxes & fees

14 Oct - 15 Oct

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

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

A vineyard landscape with rows of grapevines and a person holding a glass.

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

9. Locanda le Piazze

Castellina in Chianti

Mark

S$538

includes taxes & fees

24 Sept - 25 Sept

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

A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."

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

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

10. Four Points by Sheraton Siena

Scacciapensieri

Raul

S$231

includes taxes & fees

12 Oct - 13 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

A restaurant with a table set for two, overlooking a scenic landscape.

A villa with a swimming pool, outdoor seating, and a garden.

11. Relais Vignale & Spa

Radda in Chianti

Maaya

S$294

includes taxes & fees

8 Oct - 9 Oct

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

12. Hotel Borgo San Luigi

Monteriggioni

Raman

S$312

includes taxes & fees

13 Oct - 14 Oct

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

A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

13. Hotel Villa Campomaggio

Radda in Chianti

Krishna

S$268

includes taxes & fees

13 Oct - 14 Oct

A stone building with a swimming pool, surrounded by trees and a view of the landscape.

A stone building with a paved entrance and a well-maintained garden with potted plants.

A stone-walled terrace with a table set for two, a bottle, and candles.

A stone wall with a rustic stone building partially visible behind it.

14. Relais la Costa - Dimora Storica

Monteriggioni

corey

S$243

includes taxes & fees

8 Oct - 9 Oct

A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

A modern living room with a glass coffee table, white sofas, and decorative plants.

A hotel entrance with a sign reading "HOTEL EXPO".

A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.

15. Hotel Executive

Scacciapensieri

Susan

S$145

includes taxes & fees

12 Oct - 13 Oct

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

A breakfast buffet with various pastries, fruits, and beverages.

A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.

A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.

16. Villa Sabolini

Colle di Val d'Elsa

Andrew

S$221

includes taxes & fees

6 Oct - 7 Oct

A large building with multiple rooms, surrounded by a field of lavender.

An arched brick corridor leading to a dining area with tables set for a meal.

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

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

17. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Hannah

S$818

includes taxes & fees

8 Oct - 9 Oct

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

A fountain in a park with tall trees and a clear sky.

A neatly made breakfast tray on a bed with a tray of bread, fruit, juice, and tea, in a room with a bed, curtains, and a painting on the wall.

A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.

18. Hotel Il Piccolo Castello

Monteriggioni

Ian

S$214

includes taxes & fees

15 Sept - 16 Sept

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

A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.

19. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

S$300

includes taxes & fees

5 Oct - 6 Oct

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 clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

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

20. Villa San Lucchese

Poggibonsi

Simona

S$182

includes taxes & fees

14 Oct - 15 Oct

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Top San Leonino Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Beautiful room with amazing views, clean and well-maintained. Excellent breakfast."

Hotel Chiusarelli

10/10 Excellent

"Excellent location. Easy parking and helpful staff."

Fattoria di Vegi

10/10 Excellent

"Incredible magical place. Couldn’t recommend it more…"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Excellent location. Even though a walking only area, easy walk. Great service and breakfast was delicious. My only complaint is the included breakfast was only for 1 person."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Lovely hotel, great location, good pool, friendly staff, good food"

Hotel Italia

8/10 Good

"Clean, well maintained property that you’ll feel safe spending the night."

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

NH Siena

10/10 Excellent

"Superior room not great, Very small with leaking shower and other issues. Upgraded to suite on 5th floor which was excellent. Very spacious, huge bathroom with bath and walk in shower. Great views and comfortable bed."

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The staff were very friendly and helpful. The bar service is the best."

More cheap stays in San Leonino

Cannon d'Oro

Via Montanini 28 Siena SI

S$142

24 Sept - 25 Sept

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

S$171

14 Oct - 15 Oct

includes taxes & fees

7.8/10 Good! (435 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

S$225

14 Oct - 15 Oct

includes taxes & fees

8.8/10 Excellent! (106 reviews)

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI

S$239

12 Oct - 13 Oct

includes taxes & fees

9/10 Wonderful! (20 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

S$255

11 Oct - 12 Oct

includes taxes & fees

10/10 Exceptional! (49 reviews)

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 4.7 mi (7.5 km) from the heart of San Leonino, La Certosa di Pontignano is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Hotel Athena and Villa I Barronci Resort & Spa. 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 kitchenware. 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.

San Leonino Hotels from S$96

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leonino

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for San Leonino hotels

1. Belvedere di San Leonino

2. Hotel Casafrassi

3. Castello La Leccia

4. La Certosa di Pontignano

5. Hotel Colle Etrusco Salivolpi

6. Dievole Wine Resort

7. Agriturismo San Sano

8. Villa Montarioso

9. Locanda le Piazze

10. Four Points by Sheraton Siena

11. Relais Vignale & Spa

12. Hotel Borgo San Luigi

13. Hotel Villa Campomaggio

14. Relais la Costa - Dimora Storica

15. Hotel Executive

16. Villa Sabolini

17. Borgo Scopeto Wine & Country Relais

18. Hotel Il Piccolo Castello

19. Villa Scacciapensieri Boutique Hotel

20. Villa San Lucchese

Top San Leonino Hotel Reviews

Palazzo Ravizza

Hotel Chiusarelli

Fattoria di Vegi

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Casolare Le Terre Rosse

Hotel Italia

Hotel Athena

NH Siena

Villa Scacciapensieri Boutique Hotel

More cheap stays in San Leonino

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Antico Borgo Poggiarello

Torre del Fuggisole

Porta Pispini Residence

Frequently asked questions

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