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 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

$123

$142 total

includes taxes & fees

Oct 15 - Oct 16

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.

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

$98

$117 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 wooden door, outdoor seating, and a pergola with vines.

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.

3. Agriturismo San Sano

Gaiole in Chianti

$74

$86 total

includes taxes & fees

Oct 18 - Oct 19

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.

4. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

$102

$115 total

includes taxes & fees

Oct 26 - Oct 27

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

5. Hotel Casafrassi

Castellina in Chianti

$61

$74 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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.

6. Sangallo Park Hotel

Vico Alto

$112

$129 total

includes taxes & fees

Oct 25 - Oct 26

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

7. Hotel Executive

Scacciapensieri

$101

$117 total

includes taxes & fees

Oct 25 - Oct 26

A pool with clear water and a row of white lounge chairs facing a scenic hillside view.

A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.

An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.

A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

8. Palazzo Squarcialupi

Castellina in Chianti

$205

$232 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

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

9. Castello di Tornano Wine Resort

Gaiole in Chianti

$143

$166 total

includes taxes & fees

Oct 29 - Oct 30

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

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

10. Hotel Il Piccolo Castello

Monteriggioni

$131

$152 total

includes taxes & fees

Oct 26 - Oct 27

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 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.

11. Villa San Lucchese

Poggibonsi

$105

$123 total

includes taxes & fees

Oct 30 - Oct 31

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

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

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.

12. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

$94

$113 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

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

13. Fattoria di Vegi

Castellina in Chianti

$247

$279 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

14. Dievole Wine Resort

Castelnuovo Berardenga

$296

$335 total

includes taxes & fees

Oct 28 - Oct 29

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.

15. Hotel Borgo San Luigi

Monteriggioni

$157

$180 total

includes taxes & fees

Oct 31 - Nov 1

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

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

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

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

16. Four Points by Sheraton Siena

Scacciapensieri

$148

$168 total

includes taxes & fees

Oct 25 - Oct 26

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.

17. Relais la Costa - Dimora Storica

Monteriggioni

$154

$175 total

includes taxes & fees

Oct 11 - Oct 12

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.

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

18. Hotel Villa Campomaggio

Radda in Chianti

$190

$216 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

19. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

$181

$206 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

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

20. Villa Sabolini

Colle di Val d'Elsa

$128

$145 total

includes taxes & fees

Oct 19 - Oct 20

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Go beyond your typical stay in San Leonino

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Family friendly

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Check out reviews of San Leonino hotels guests love

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"

Poderi Arcangelo

8/10 Good

"We enjoyed our stay. The pool, hotel grounds and location were truly amazing. The food was okay but we enjoyed eating off site more. The farmhouse is very quaint and charming. You can hear others in the farmhouse. It was luxurious in many ways and more basic in other ways. But all together a wonderful stay. I would recommend for sure."

Hotel Minerva

10/10 Excellent

"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."

Borgo Scopeto Wine & Country Relais

8/10 Good

"Staff are nice!"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."

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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