Hotels in San Leonino

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Where to stay in San Leonino?

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

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

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

1. La Certosa di Pontignano

Castelnuovo Berardenga

$97

$116 total

includes taxes & fees

Oct 19 - Oct 20

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 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.

2. Agriturismo San Sano

Gaiole in Chianti

$73

$85 total

includes taxes & fees

Oct 18 - Oct 19

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

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

A rustic stone building with a garden in front.

3. Belvedere di San Leonino

Castellina in Chianti

$122

$141 total

includes taxes & fees

Oct 15 - Oct 16

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

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

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

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

4. Hotel Casafrassi

Castellina in Chianti

$60

$73 total

includes taxes & fees

Oct 8 - Oct 9

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 stone building with a wooden bench outside.

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

5. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

$101

$114 total

includes taxes & fees

Oct 26 - Oct 27

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 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.

6. Hotel Il Piccolo Castello

Monteriggioni

$112

$131 total

includes taxes & fees

Nov 1 - Nov 2

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

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

A bathroom with a sink, mirror, and shower.

A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.

7. Sangallo Park Hotel

Vico Alto

$107

$121 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

8. Villa San Lucchese

Poggibonsi

$104

$122 total

includes taxes & fees

Oct 30 - Oct 31

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

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.

A stone building with a tower, surrounded by people dining at tables with candles.

9. Castello di Tornano Wine Resort

Gaiole in Chianti

$142

$165 total

includes taxes & fees

Oct 26 - Oct 27

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".

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

10. Hotel Executive

Scacciapensieri

$91

$103 total

includes taxes & fees

Nov 1 - Nov 2

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.

11. Fattoria di Vegi

Castellina in Chianti

$245

$277 total

includes taxes & fees

Oct 26 - Oct 27

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

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.

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

12. Dievole Wine Resort

Castelnuovo Berardenga

$294

$332 total

includes taxes & fees

Oct 28 - Oct 29

A courtyard with a statue, stone walls, and a reception sign.

An outdoor dining area with tables and chairs, surrounded by trees and a stone wall.

A wooden pathway leading to a pool area with a gazebo and potted plants.

A spacious room with a high ceiling, wooden beams, and a chandelier. There are tables and chairs arranged for dining, and a wine rack filled with bottles.

13. Relais Della Rovere

Colle di Val d'Elsa

$129

$147 total

includes taxes & fees

Oct 30 - Oct 31

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 landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

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

14. Hotel Villa Campomaggio

Radda in Chianti

$166

$189 total

includes taxes & fees

Nov 3 - Nov 4

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

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

15. Villa Sabolini

Colle di Val d'Elsa

$81

$93 total

includes taxes & fees

Nov 3 - Nov 4

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

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

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

16. Hotel Borgo San Luigi

Monteriggioni

$119

$139 total

includes taxes & fees

Nov 2 - Nov 3

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

A spacious living room with a wooden staircase, a sofa, a dining table, and a radiator.

17. Relais la Costa - Dimora Storica

Monteriggioni

$153

$173 total

includes taxes & fees

Oct 11 - Oct 12

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

18. Four Points by Sheraton Siena

Scacciapensieri

$139

$156 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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.

19. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

$117

$135 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

20. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$190

$215 total

includes taxes & fees

Oct 18 - Oct 19

View all properties

Go beyond your typical stay in San Leonino

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Check out reviews of San Leonino hotels guests love

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"A peaceful luxurious stay with amazing amenities, 6 star service & and amazing dinner restaurant."

Poderi Arcangelo

10/10 Excellent

"Beautiful property, nice and helping staff. We enjoy our stay ."

Villa I Barronci Resort & Spa

8/10 Good

"Under renovation so it could have been better"

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Hotel Athena

10/10 Excellent

"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Absolutely stunning property with amazing staff. Tons of wineries close by and touring thru San Gimignano was fascinating. Definitely 5/5."

La Certosa di Pontignano

10/10 Excellent

"good to stay"

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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