Hotels in San Leonino

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Where to stay in San Leonino?

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 rustic stone building with a garden in front.

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

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

$106

$123 total

includes taxes & fees

Oct 16 - Oct 17

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.

2. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

$95

$113 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

3. Hotel Casafrassi

Castellina in Chianti

$60

$73 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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.

4. Hotel Il Piccolo Castello

Monteriggioni

$102

$120 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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.

5. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

$122

$138 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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

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

6. Hotel Executive

Scacciapensieri

$90

$102 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.

A bathroom with a sink, mirror, and shower.

A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

7. Sangallo Park Hotel

Vico Alto

$95

$108 total

includes taxes & fees

Nov 8 - Nov 9

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

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

8. Dievole Wine Resort

Castelnuovo Berardenga

$272

$308 total

includes taxes & fees

Nov 9 - Nov 10

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

A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.

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

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

9. Fattoria di Vegi

Castellina in Chianti

$243

$274 total

includes taxes & fees

Oct 26 - Oct 27

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

A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.

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.

10. Castello La Leccia

Castellina in Chianti

$199

$224 total

includes taxes & fees

Nov 2 - Nov 3

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

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

11. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

$110

$128 total

includes taxes & fees

Nov 1 - Nov 2

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.

12. Villa San Lucchese

Poggibonsi

$112

$124 total

includes taxes & fees

Nov 4 - Nov 5

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.

13. Hotel Borgo San Luigi

Monteriggioni

$125

$145 total

includes taxes & fees

Nov 9 - Nov 10

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

A stone archway leading to a window with a view of tall trees and a distant landscape.

A historic stone building with a large arched window and a small balcony.

14. Castello di Tornano Wine Resort

Gaiole in Chianti

$152

$176 total

includes taxes & fees

Oct 25 - Oct 26

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

A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

A buffet area with various fruits and a bar with bottles.

A courtyard with outdoor seating, stone walls, and a staircase.

15. Hotel Palazzo San niccolò & Spa

Radda in Chianti

$97

$114 total

includes taxes & fees

Nov 11 - Nov 12

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

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

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.

16. Hotel Villa Campomaggio

Radda in Chianti

$165

$188 total

includes taxes & fees

Nov 3 - Nov 4

A spa area with a stone ceiling, a large bathtub, and a seating area.

A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

A garden with a gravel path leading to a white metal table and chairs, surrounded by red roses and a large terracotta pot.

A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.

17. Palazzo Squarcialupi

Castellina in Chianti

$192

$218 total

includes taxes & fees

Oct 18 - Oct 19

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

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

18. Four Points by Sheraton Siena

Scacciapensieri

$138

$155 total

includes taxes & fees

Nov 2 - Nov 3

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

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

A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.

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

19. Villa Sabolini

Colle di Val d'Elsa

$95

$109 total

includes taxes & fees

Nov 11 - Nov 12

A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.

A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

20. Borgo Vescine

Radda in Chianti

$466

$521 total

includes taxes & fees

Nov 7 - Nov 8

View all properties

Go beyond your typical stay in San Leonino

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Pool

Hot tub

Family friendly

Farm

Check out reviews of San Leonino hotels guests love

Hotel Italia

10/10 Excellent

"Staff and hotel was great."

Hotel Athena

10/10 Excellent

"Reception staff very friendly and helpful. Room on top floor had two full length windows with spectacular views. Older property but updated nicely; not modern but comfortable. Comfy bed, linens and pillows. Nice breakfast with lots of variety. There are two floors that have breakfast - the lowest level is more spacious and had food replaced more quickly than upper level. Hotel seems far, but everything is 5 to 15 minutes away. We found our favorite wine spot just a 5 minute walk away at Tuscan Wine School. But do go to the rooftop terrace for lovely views."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

Fattoria di Vegi

10/10 Excellent

"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"Beautiful Borgo with views over Sienna and wonderful Tuscan countryside. In peak summer there is a family pool and adults only pool. The family pool was quiet and nice area to relax. About 20-30 mins to Siena we explored lots of lovely hill top places for dinner each night. Pool side dining was ok, club sandwiches that type of thing not extensive choice but adequate. Stunning views, good location to explore surrounding area. Would definitely recommend. I stayed with my family two boys age 9 and 13 and they loved it. Accommodation was very comfortable and spacious."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

Frequently asked questions

What hotels do travelers recommend in San Leonino?

Guests like Hotel Athena, La Certosa di Pontignano and NH Siena.

Can I book refundable accommodations in San Leonino?

If you need the flexibility to change your travel plans to San Leonino, most hotels provide refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in San Leonino be like during my visit?

The warmest months in San Leonino are usually August and July with an average temp of 72°F. January and February are the chilliest months when the average temp is 44°F. The rainiest months are November and October.

Why should I book my San Leonino hotel with Hotels.com?

There are plenty of reasons to book your San Leonino travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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