San Leonino Holiday Rentals, Castellina in Chianti: Private House Rentals

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Go beyond your typical stay in San Leonino

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Hot tub

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Farm

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Our top choices for San Leonino hotels

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

1. Sangallo Park Hotel

Vico Alto

Linda

฿3,770

฿4,261 total

includes taxes & fees

1 Nov - 2 Nov

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

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

2. Four Points by Sheraton Siena

Scacciapensieri

Ralph

฿4,953

฿5,639 total

includes taxes & fees

27 Oct - 28 Oct

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 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".

3. Hotel Executive

Scacciapensieri

Susan

฿3,074

฿3,495 total

includes taxes & fees

1 Nov - 2 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 narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

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

4. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

฿9,938

฿11,236 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

5. Hotel Il Piccolo Castello

Monteriggioni

Frank

฿3,799

฿4,446 total

includes taxes & fees

1 Nov - 2 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A rustic stone building with a garden in front.

6. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

฿4,139

฿4,782 total

includes taxes & fees

15 Oct - 16 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.

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.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

7. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

฿3,281

฿3,913 total

includes taxes & fees

19 Oct - 20 Oct

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

A swimming pool surrounded by lush greenery and a stone pathway.

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.

8. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

฿6,449

฿7,284 total

includes taxes & fees

19 Oct - 20 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.

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

9. Relais Vignale & Spa

Radda in Chianti

Ali

฿5,456

฿7,171 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

10. Hotel Casafrassi

Castellina in Chianti

Rita

฿2,042

฿2,475 total

includes taxes & fees

8 Oct - 9 Oct

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

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.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

11. Villa San Lucchese

Poggibonsi

James

฿3,533

฿4,115 total

includes taxes & fees

30 Oct - 31 Oct

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A vineyard landscape with rows of grapevines and a person holding a glass.

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

A modern interior with a bar area, seating, and a staircase.

12. Locanda le Piazze

Castellina in Chianti

Tara

฿11,570

฿12,956 total

includes taxes & fees

12 Oct - 13 Oct

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

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

A swimming pool with lounge chairs and an umbrella, surrounded by trees.

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

13. Fattoria di Vegi

Castellina in Chianti

Robin

฿8,302

฿9,361 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

14. Hotel Villa Campomaggio

Radda in Chianti

Dario

฿6,386

฿7,253 total

includes taxes & fees

1 Nov - 2 Nov

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.

15. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

฿3,416

฿3,872 total

includes taxes & fees

26 Oct - 27 Oct

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

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 restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

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

16. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

฿18,642

฿20,887 total

includes taxes & fees

11 Oct - 12 Oct

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.

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

A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

17. Palazzo Squarcialupi

Castellina in Chianti

yvette

฿6,887

฿7,805 total

includes taxes & fees

21 Oct - 22 Oct

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

An arched brick corridor leading to a dining area with tables set for a meal.

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

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

18. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

GUANGMIN

฿17,947

฿20,122 total

includes taxes & fees

28 Oct - 29 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 spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

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

19. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

฿3,957

฿4,581 total

includes taxes & fees

1 Nov - 2 Nov

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.

20. Hotel Borgo San Luigi

Monteriggioni

Raman

฿4,042

฿4,712 total

includes taxes & fees

1 Nov - 2 Nov

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Top San Leonino Hotel Reviews

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."

More cheap stays in San Leonino

Cannon d'Oro

Via Montanini 28 Siena SI

฿1,947

฿2,332 total

28 Oct - 29 Oct

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

฿4,154

฿4,760 total

5 Oct - 6 Oct

includes taxes & fees

7.8/10 Good! (442 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

฿4,702

฿5,363 total

28 Oct - 29 Oct

includes taxes & fees

10/10 Exceptional! (50 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

฿4,896

฿5,576 total

19 Oct - 20 Oct

includes taxes & fees

8.8/10 Excellent! (108 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

฿2,442

฿5,846 total

20 Oct - 21 Oct

includes taxes & fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

Frequently asked questions

Where is the best place to stay in San Leonino?

Located 7.4 mi (11.9 km) from the heart of San Leonino, Hotel Athena is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are La Certosa di Pontignano and NH Siena. See all available top hotels, or vacation rentals in San Leonino.

What are some of the best holiday rentals that San Leonino has to offer?

Borgo Argiano: This holiday home rental outside of San Leonino is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in San Leonino.

If I need to cancel my hotel reservation in San Leonino, will I receive a refund?

Yes! Most hotel room reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in San Leonino.

How is it staying in San Leonino?

Those travelling to San Leonino will definitely enjoy the sights to see and things to do. In San Leonino, there are 2 hotels and other accommodation options to choose from. Find out more about San Leonino.

What is there to see in San Leonino?

Places to visit in the wider area include City Hall Castellina In Chianti, Castello di Radda Winery and Meleto Castle. You'll also find Isole e Olena Winery and Fortezza Medicea in the area. Take a look at what more there is to see and do in Expedia's San Leonino guide.

What's the seasonal weather like in San Leonino?

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 Leonino is 944 mm.

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More ways to book

Book Hotels in San Leonino on Expedia.it

Find hotels in San Leonino from ฿2,332

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leonino

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for San Leonino hotels

1. Sangallo Park Hotel

2. Four Points by Sheraton Siena

3. Hotel Executive

4. Dievole Wine Resort

5. Hotel Il Piccolo Castello

6. Belvedere di San Leonino

7. La Certosa di Pontignano

8. Villa Scacciapensieri Boutique Hotel

9. Relais Vignale & Spa

10. Hotel Casafrassi

11. Villa San Lucchese

12. Locanda le Piazze

13. Fattoria di Vegi

14. Hotel Villa Campomaggio

15. Hotel Colle Etrusco Salivolpi

16. Hotel Le Fontanelle

17. Palazzo Squarcialupi

18. Borgo Scopeto Wine & Country Relais

19. Palazzo Leopoldo Dimora Storica & Spa

20. Hotel Borgo San Luigi

Top San Leonino Hotel Reviews

Villa I Barronci Resort & Spa

Fattoria di Vegi

Hotel Athena

Hotel Casolare Le Terre Rosse

La Certosa di Pontignano

Poderi Arcangelo

Hotel Minerva

Borgo Scopeto Wine & Country Relais

Grand Hotel Continental Siena – Starhotels Collezione

More cheap stays in San Leonino

Cannon d'Oro

Piccolo Hotel Etruria

Torre del Fuggisole

Albergo Centrale

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

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