San Sano Holiday Rentals, Gaiole in Chianti: Private House Rentals

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Our top choices for San Sano hotels

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.

1. Agriturismo San Sano

Gaiole in Chianti

Glen

1.884.140 ₫

2.188.639 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

2. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

7.052.170 ₫

7.989.557 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

A sunlit patio with a glass roof, stone walls, and outdoor seating.

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

A stone building with a garden, tall trees, and a clear blue sky.

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

Gaiole in Chianti

Michelle

8.547.927 ₫

9.692.817 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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

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

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.

4. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

9.876.201 ₫

11.154.034 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

A table set for breakfast with various dishes, drinks, and a newspaper.

5. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

14.165.243 ₫

15.871.090 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

6. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

3.938.535 ₫

4.564.558 ₫ total

includes taxes & fees

25 Oct - 26 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.

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

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.

7. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Leslie

2.457.574 ₫

2.935.501 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A historic stone building with multiple windows and a courtyard.

A pool area with lounge chairs and a service person attending to a guest.

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

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.

8. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

19.858.063 ₫

22.133.192 ₫ total

includes taxes & fees

25 Oct - 26 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.

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

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

9. Relais Vignale & Spa

Radda in Chianti

Ali

4.206.381 ₫

5.517.973 ₫ total

includes taxes & fees

16 Oct - 17 Oct

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 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.

10. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

3.016.099 ₫

3.491.837 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A rustic stone building with a garden in front.

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

11. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

2.802.270 ₫

3.256.091 ₫ total

includes taxes & fees

16 Oct - 17 Oct

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 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."

12. Four Points by Sheraton Siena

Scacciapensieri

Ralph

3.585.447 ₫

4.031.056 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

13. Hotel Casafrassi

Castellina in Chianti

Stuart

1.556.596 ₫

1.886.384 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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

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

14. Castello La Leccia

Castellina in Chianti

Eva

5.195.839 ₫

5.831.508 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

15. Hotel Executive

Scacciapensieri

Andras

2.342.808 ₫

2.664.153 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

A building with a brick facade, arched entrance, and multiple windows covered in green ivy.

A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

16. Tenuta CorteDomina

Radda in Chianti

Edgar

4.611.745 ₫

5.189.004 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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 rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

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

17. Borgo Vescine

Radda in Chianti

Natalie

12.109.787 ₫

13.552.936 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

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

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

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

18. Hotel Villa Campomaggio

Radda in Chianti

Dario

4.274.042 ₫

4.875.574 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A stone building with arched windows, a grassy courtyard, and outdoor seating.

A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

A person relaxing in a clear pool surrounded by natural scenery.

An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.

19. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

9.004.431 ₫

10.137.131 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

A modern kitchen with a large window, wooden ceiling, and a view of a forested area.

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

20. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

6.943.747 ₫

7.811.716 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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Top San Sano Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Lovely hotel inside the city walls, if you are driving there and want to take advantage of the hotel car park (availability not guaranteed) you have to follow quite specific instructions to get there so as not to get a fine, they are quite easy to follow though. Dogs accepted and they provided dog beds and water for the dogs which was nice, the dogs are also allowed throughout the hotel. The views from the bedroom were amazing, as is the same from the lovely garden & terrace. Breakfast was great, lovely bread and the best marmalade ever, as well as cake, eggs, etc. bar is just open from 5pm but you can get a drink earlier if it takes your fancy"

Salvadonica - Borgo del Chianti

8/10 Good

"Lit un peut moins confortable"

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Gorgeous hotel in the heart of historic Siena."

Hotel Italia

10/10 Excellent

"Staff and hotel was great."

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."

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."

Four Points by Sheraton Siena

8/10 Good

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

More cheap stays in San Sano

Cannon d'Oro

Via Montanini 28 Siena SI

1.484.043 ₫

1.719.511 ₫ total

9 Nov - 10 Nov

includes taxes & fees

7.8/10 Good! (259 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

2.000.252 ₫

2.287.341 ₫ total

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (50 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

2.184.511 ₫

2.490.026 ₫ total

4 Nov - 5 Nov

includes taxes & fees

7.8/10 Good! (452 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

2.457.574 ₫

2.790.396 ₫ total

3 Nov - 4 Nov

includes taxes & fees

8.8/10 Excellent! (113 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

2.604.000 ₫

2.980.485 ₫ total

15 Oct - 16 Oct

includes taxes & fees

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

1.855.510 ₫

4.442.440 ₫ total

22 Oct - 23 Oct

includes taxes & fees

Hotels in San Sano with star rating

Frequently asked questions

What's the seasonal weather in San Sano?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for San Sano is 935 mm.

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Book Hotels in San Sano on Expedia.it

Find hotels in San Sano from 1.719.511 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Sano

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for San Sano hotels

1. Agriturismo San Sano

2. Dievole Wine Resort

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

4. Borgo Scopeto Wine & Country Relais

5. Hotel Le Fontanelle

6. Castello di Tornano Wine Resort

7. La Certosa di Pontignano - Place of Charme

8. Borgo San Felice Resort

9. Relais Vignale & Spa

10. Palazzo Leopoldo Dimora Storica & Spa

11. Belvedere di San Leonino

12. Four Points by Sheraton Siena

13. Hotel Casafrassi

14. Castello La Leccia

15. Hotel Executive

16. Tenuta CorteDomina

17. Borgo Vescine

18. Hotel Villa Campomaggio

19. Pieve Aldina - Relais & Châteaux

20. Chapter Chianti, a Member of Design Hotels

Top San Sano Hotel Reviews

Palazzo Ravizza

Salvadonica - Borgo del Chianti

Hotel Casolare Le Terre Rosse

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Italia

Castello di Spaltenna- Small Luxury Hotels of the World

Fattoria di Vegi

Borgo Scopeto Wine & Country Relais

Four Points by Sheraton Siena

More cheap stays in San Sano

Cannon d'Oro

Torre del Fuggisole

Piccolo Hotel Etruria

Albergo Centrale

Porta Pispini Residence

Castello di Bossi

Hotels in San Sano with star rating

Frequently asked questions

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