San Leolino Hotel & Accommodation Deals 2026 from AU$156 - Compare prices by date

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Go beyond your typical stay in San Leolino

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Our top choices for San Leolino hotels

A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.

A poolside area with a swimming pool, lounge chairs, and a grassy lawn.

An outdoor dining area with long tables set for a meal, surrounded by greenery and trees.

An aerial view of a villa surrounded by lush greenery and rolling hills.

1. Il Verreno

Ambra

Minna

AU$356

includes taxes & fees

13 Oct - 14 Oct

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

A modern living room with a white sofa, armchairs, and a coffee table.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

2. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

AU$437

includes taxes & fees

7 Oct - 8 Oct

A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.

An outdoor dining area with tables and chairs, overlooking a scenic view of a coastal town during sunset.

A four-poster bed with a view of the outdoors, a desk with a chair, and a sofa in a room with wooden beams on the ceiling.

A cozy living room with a fireplace, wooden bookshelves, and a decorative mirror.

3. Villa Sassolini Country Boutique Hotel

Montevarchi

Peter

AU$336

includes taxes & fees

7 Oct - 8 Oct

A spacious lobby with a reception desk, seating area, and a large vase.

A patio with a round table and chairs, potted plants, and a view of the building's interior.

A modern hotel lobby with a curved reception desk, seating area, and a bar.

A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.

4. Hotel Valdarno

Montevarchi

Emmanuel

AU$178

includes taxes & fees

28 Sept - 29 Sept

A person pouring a liquid from a bottle into a glass.

A modern interior with a yellow sofa, blue armchair, and a dining area with chairs and a table.

A modern building with a glass facade, a car parked in front, and a well-lit entrance area.

A glass table with a sandwich and a drink, a yellow sofa, and a fireplace with flames.

5. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

AU$185

includes taxes & fees

26 Sept - 27 Sept

A buffet with various food items and utensils.

A hotel room with a large bed, bedside tables, a nightstand, a vase with flowers, a tray with pastries, a teapot, and a glass of orange juice.

A modern lobby with a reception desk, two seating areas with orange chairs, and a marble floor.

A covered outdoor seating area with wicker furniture and a potted plant.

6. Hotel Il Viandante

Terranuova Bracciolini

Michelle

AU$181

includes taxes & fees

20 Sept - 21 Sept

A stone building with outdoor seating and a pool in the background.

A dining table set with various foods, including meats, cheeses, and fruits.

A stone house with a paved driveway and a lawn, surrounded by trees and a white car parked in front.

A swimming pool with a breakfast tray of fruits and juice, surrounded by trees and a clear sky.

7. B&B Country House Poggio del Drago

Civitella in Val di Chiana

Kristen

AU$194

includes taxes & fees

23 Sept - 24 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.

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.

8. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

AU$206

includes taxes & fees

13 Oct - 14 Oct

A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.

A hotel room with a bed, a TV, a desk, and a mirror.

A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.

A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

9. Delta Hotel

Montevarchi

weixing

AU$198

includes taxes & fees

26 Sept - 27 Sept

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

A stone-walled room with a sofa, a coat rack, and a window with curtains.

A rectangular swimming pool with a view of mountains in the background.

A stone house with a tiled roof, surrounded by greenery and a gravel path.

10. Podere L'Aquila

Gaiole in Chianti

AU$653

includes taxes & fees

15 Sept - 16 Sept

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

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

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.

11. Agriturismo San Sano

Gaiole in Chianti

Ernesto

AU$131

includes taxes & fees

11 Oct - 12 Oct

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

12. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Rama

AU$629

includes taxes & fees

5 Oct - 6 Oct

A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

A restaurant interior with tables set for dining, a kitchen area, and a wine display.

A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

A hotel lobby with a brick archway, a reception desk, and potted plants.

13. Hotel Le Capanne

Arezzo

Georg

AU$196

includes taxes & fees

25 Sept - 26 Sept

A villa with a swimming pool, outdoor seating, and a tennis court.

A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.

An aerial view of a property with a swimming pool, tennis court, and vineyard.

A pool area with lounge chairs and umbrellas, a stone planter with flowers, and a building with balconies in the background.

14. Villa Curina Resort

Castelnuovo Berardenga

Joe

AU$258

includes taxes & fees

17 Sept - 18 Sept

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

A stone building with outdoor seating and a garden with roses.

15. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

AU$1,076

includes taxes & fees

11 Oct - 12 Oct

A dining table set with various dishes, glasses of wine, and a vase of flowers.

A yellow building with a stone wall and a swimming pool reflecting the building and trees.

An outdoor dining area with tables set for a meal, surrounded by stone walls and potted plants.

16. Palazzo Tiglio - A Small Luxury Hotels of the World

Bucine

David

AU$391

includes taxes & fees

4 Oct - 5 Oct

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

17. Dievole Wine Resort

Castelnuovo Berardenga

Karamjit

AU$565

includes taxes & fees

11 Oct - 12 Oct

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

18. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

"Ultimo Mulino Hotel was amazing! The property is so peaceful and beautiful. We had breakfast both mornings and ate at their on site restaurant both evenings. The food was delicious and the staff was incredible. Leno was our server both nights- she was amazing and so helpful making suggestions on food and wines. We also enjoyed the spa for the wellness package and a couples massage for our honeymoon. We highly recommend this to everyone! It was so relaxing and worth the cost."

Hannah

AU$191

includes taxes & fees

6 Oct - 7 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.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

19. Relais Vignale & Spa

Radda in Chianti

Maaya

AU$317

includes taxes & fees

13 Oct - 14 Oct

A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.

A hallway with a decorative archway leading to a door, a row of plants on the left, and a wall-mounted lamp on the right.

A spa area with a circular hot tub surrounded by mosaic tiles, a stone bench, and a small table with a bowl and a candle.

A rooftop terrace with outdoor seating, a pergola, and a view of hills.

20. Il Gentiluomo Hotel & SPA

Arezzo

Luis Mauricio

AU$120

includes taxes & fees

21 Sept - 22 Sept

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Top San Leolino Hotel Reviews

Recent Reviews in San Leolino

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!"

Castello di Leonina Relais

10/10 Excellent

"."

Borgo Vescine

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."

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."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"All the staff in the hotel were very helpful and we would like to stay there again."

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

Fattoria di Vegi

10/10 Excellent

"Amazing! I wish I could have stayed forever!"

Palazzo Ravizza

8/10 Good

"Great view from our room, lovely courtyard, nice staff. Tricky if you’re driving."

More cheap accommodation in San Leolino

Cannon d'Oro

Via Montanini 28 Siena SI

AU$156

29 Sept - 30 Sept

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

AU$189

13 Oct - 14 Oct

includes taxes & fees

7.8/10 Good! (435 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

AU$246

13 Oct - 14 Oct

includes taxes & fees

8.8/10 Excellent! (106 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

AU$281

11 Oct - 12 Oct

includes taxes & fees

10/10 Exceptional! (49 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

AU$291

13 Sept - 14 Sept

includes taxes & fees

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 Leolino?

When visiting San Leolino, the best area to stay is within the hamlet itself or in the immediately surrounding countryside, particularly towards the charming town of Castellina in Chianti.The hamlet of San Leolino itself is very small, centred around its historic Romanesque church, Pieve di San Leolino. Staying directly within the hamlet or in a nearby villa allows for a truly tranquil experience, surrounded by rolling vineyards and olive groves. It's a place where you can enjoy the quiet beauty of the Tuscan landscape, often with stunning views across the valley.Couples seeking a romantic and peaceful escape will find the immediate vicinity of San Leolino perfect. Many accommodations here are renovated farmhouses or boutique properties that offer privacy, beautiful scenery, and opportunities for wine tasting at nearby vineyards. You'll often find properties with private pools and terraces, ideal for enjoying a glass of Chianti while watching the sunset.Families might prefer staying in a villa or agriturismo slightly closer to Castellina in Chianti, which is just a short drive away. This offers the same peaceful setting but with easier access to amenities like grocery shops, restaurants, and a few local artisan stores in Castellina's historic centre.

When is the best time to go to San Leolino?

The best times to visit San Leolino are typically in the spring (April to early June) and autumn (September to October) when the weather is pleasant and the region is less crowded.For those looking for comfortable temperatures for exploring the Tuscan countryside, spring offers mild weather, often with blooming wildflowers. The days are generally sunny without being overly hot, making it ideal for walking through vineyards or visiting nearby towns like Siena or Florence. You'll also find fewer tourists compared to the peak summer months.Autumn provides a similar experience with comfortable temperatures, and it's also harvest season. This is a lovely time for food and wine enthusiasts, as many local farms and vineyards offer special experiences.

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 Leolino.

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

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on San Leolino 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 Leolino?

Prices for hotels in San Leolino often vary, but you can find a great deal from AU$156 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

Book Hotels in San Leolino on Expedia.it

Search San Leolino hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leolino

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for San Leolino hotels

1. Il Verreno

2. Chapter Chianti, a Member of Design Hotels

3. Villa Sassolini Country Boutique Hotel

4. Hotel Valdarno

5. Moody smart & comfy Hotel

6. Hotel Il Viandante

7. B&B Country House Poggio del Drago

8. La Certosa di Pontignano

9. Delta Hotel

10. Podere L'Aquila

11. Agriturismo San Sano

12. Castello di Spaltenna- Small Luxury Hotels of the World

13. Hotel Le Capanne

14. Villa Curina Resort

15. Borgo San Felice Resort

16. Palazzo Tiglio - A Small Luxury Hotels of the World

17. Dievole Wine Resort

18. Ultimo Mulino Wellness Country Hotel

19. Relais Vignale & Spa

20. Il Gentiluomo Hotel & SPA

Top San Leolino Hotel Reviews

Recent Reviews in San Leolino

Hotel Athena

Castello di Leonina Relais

Borgo Vescine

NH Siena

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Borgo San Felice Resort

Fattoria di Vegi

Palazzo Ravizza

More cheap accommodation in San Leolino

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

Explore a world of travel with Expedia

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