San Leonino Hotel & Accommodation Deals 2026 from AU$105 - Compare prices by date

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

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

A rustic stone building with a garden in front.

1. Belvedere di San Leonino

Castellina in Chianti

Seong Won

AU$205

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

A building with arched windows, a courtyard with a pond, and a metal fence.

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

AU$105

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 pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

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

3. Castello La Leccia

Castellina in Chianti

Samuel

AU$502

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.

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

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.

4. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

AU$209

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

5. Dievole Wine Resort

Castelnuovo Berardenga

Karamjit

AU$502

includes taxes & fees

14 Oct - 15 Oct

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

A stone building with a wooden bench outside.

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

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

6. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

AU$178

includes taxes & fees

20 Sept - 21 Sept

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

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

A stone building with a window and a light fixture.

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

7. Agriturismo San Sano

Gaiole in Chianti

Ernesto

AU$132

includes taxes & fees

14 Oct - 15 Oct

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

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

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

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

8. Villa Montarioso

Montarioso

Michael

AU$134

includes taxes & fees

14 Oct - 15 Oct

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

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.

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

9. Relais la Costa - Dimora Storica

Monteriggioni

corey

AU$267

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.

An outdoor dining area with tables and chairs, covered by a canopy, and surrounded by greenery.

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

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

10. Hotel Executive

Scacciapensieri

Susan

AU$129

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

11. Locanda le Piazze

Castellina in Chianti

Mark

AU$592

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

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

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

12. Four Points by Sheraton Siena

Scacciapensieri

Raul

AU$254

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

AU$323

includes taxes & fees

12 Oct - 13 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.

An outdoor patio with stone flooring, a table with chairs, and potted plants.

14. Hotel Borgo San Luigi

Monteriggioni

Raman

AU$365

includes taxes & fees

13 Oct - 14 Oct

A stately building with a grand entrance, multiple arches, and a well-lit facade.

A swimming pool with lounge chairs and an umbrella, surrounded by trees.

A well-decorated living room with a sofa, a coffee table, and a vase with flowers.

A restaurant with stone walls, wooden furniture, and a wine cellar.

15. Fattoria di Vegi

Castellina in Chianti

Megan

AU$555

includes taxes & fees

29 Sept - 30 Sept

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

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

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.

16. Relais Vignale & Spa

Radda in Chianti

Maaya

AU$314

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

17. Villa San Lucchese

Poggibonsi

Simona

AU$202

includes taxes & fees

14 Oct - 15 Oct

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

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

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

18. Hotel Il Piccolo Castello

Monteriggioni

Ian

AU$236

includes taxes & fees

15 Sept - 16 Sept

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

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

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

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

19. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Hannah

AU$901

includes taxes & fees

8 Oct - 9 Oct

A couple dining at an outdoor table with a view of the countryside.

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

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

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

20. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

AU$278

includes taxes & fees

12 Oct - 13 Oct

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Top San Leonino Hotel Reviews

Recent Reviews in San Leonino

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 accommodation in San Leonino

Cannon d'Oro

Via Montanini 28 Siena SI

AU$156

24 Sept - 25 Sept

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

AU$189

14 Oct - 15 Oct

includes taxes & fees

7.8/10 Good! (435 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

AU$246

14 Oct - 15 Oct

includes taxes & fees

8.8/10 Excellent! (106 reviews)

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI

AU$266

12 Oct - 13 Oct

includes taxes & fees

9/10 Wonderful! (20 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

AU$281

15 Sept - 16 Sept

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

What is the best area to stay in San Leonino?

The best area to stay in San Leonino is within the village itself or in the immediate countryside surrounding it.San Leonino is a small village, and staying directly in the village offers the convenience of walking to its few local shops and trattorias. The village is compact, with its main church, Pieve di San Leonino, as a central point of reference, and is surrounded by rolling vineyards and olive groves.For couples seeking a romantic and secluded retreat, staying in one of the agriturismos or boutique hotels just outside the village is ideal. These properties often feature stunning views of the Tuscan landscape, offer cooking classes, and provide a peaceful base from which to explore the Chianti region by car. Many have excellent restaurants on-site, superb for quiet evenings.Travellers looking for a more independent experience will find excellent villa rentals in the countryside around San Leonino. These often come with private pools and well-equipped kitchens, making them superb for those who enjoy cooking with local produce and settling into a home-away-from-home.

When is the best time to go to San Leonino?

The best time to visit San Leonino, Tuscany, is during the spring (April to June) and autumn (September to October) months.During these periods, the weather is pleasantly warm and sunny, making it ideal for exploring the rolling hills and vineyards. You'll find fewer crowds compared to the peak summer months, allowing for a more relaxed experience at local wineries and historic sites. The landscape is particularly beautiful in spring with wildflowers in bloom, and in autumn with the rich colours of the grape harvest.Couples looking for a romantic escape will find these seasons perfect. You can enjoy long walks through the countryside, intimate al fresco dining, and wine-tasting experiences without the intense summer heat or the chill of winter. It's a great time for leisurely drives along scenic routes like the Chiantigiana Road, stopping at charming villages along the way.For travellers interested in culinary experiences, autumn is particularly rewarding. This is the time for grape harvesting and olive oil production, offering opportunities for special tours and tastings.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in San Leonino.

How can I save on a hotel booking in San Leonino with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on San Leonino hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in San Leonino?

Prices for hotels in San Leonino often vary, but you can find a great deal from AU$105 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

Explore a world of travel with Expedia

Siena Holiday Rentals

Book Hotels in San Leonino on Expedia.it

Search San Leonino hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leonino

Check prices for these dates

Filter by

Property class

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. Dievole Wine Resort

6. Hotel Colle Etrusco Salivolpi

7. Agriturismo San Sano

8. Villa Montarioso

9. Relais la Costa - Dimora Storica

10. Hotel Executive

11. Locanda le Piazze

12. Four Points by Sheraton Siena

13. Hotel Villa Campomaggio

14. Hotel Borgo San Luigi

15. Fattoria di Vegi

16. Relais Vignale & Spa

17. Villa San Lucchese

18. Hotel Il Piccolo Castello

19. Borgo Scopeto Wine & Country Relais

20. Palazzo Leopoldo Dimora Storica & Spa

Top San Leonino Hotel Reviews

Recent Reviews in San Leonino

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 accommodation in San Leonino

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Antico Borgo Poggiarello

Torre del Fuggisole

Porta Pispini Residence

Frequently asked questions

Explore a world of travel with Expedia

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