San Leonino Hotel & Accommodation Deals 2026 from NZ$147 - Fully Refundable Options

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Our top choices for San Leonino hotels

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Breakfast included

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Pet-friendly

Archaeological Museum of Chianti

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

Jess

NZ$269

includes taxes & fees

27 Aug - 28 Aug

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

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

2. Hotel Casafrassi

Castellina in Chianti

Alex

NZ$157

includes taxes & fees

13 Sept - 14 Sept

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.

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.

3. La Certosa di Pontignano

Castelnuovo Berardenga

Edyta

NZ$147

includes taxes & fees

8 Sept - 9 Sept

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

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

4. Dievole Wine Resort

Castelnuovo Berardenga

Nicole

NZ$589

includes taxes & fees

26 Aug - 27 Aug

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 pool surrounded by lush greenery and vineyards, with a stone building in the background.

5. Agriturismo San Sano

Gaiole in Chianti

Paula

NZ$260

includes taxes & fees

27 Aug - 28 Aug

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

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

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

A stone building with a wooden bench outside.

6. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Scott

NZ$204

includes taxes & fees

23 Aug - 24 Aug

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

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.

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

7. Palazzo Squarcialupi

Castellina in Chianti

yvette

NZ$425

includes taxes & fees

8 Sept - 9 Sept

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.

8. Hotel Il Piccolo Castello

Monteriggioni

Ian

NZ$280

includes taxes & fees

1 Sept - 2 Sept

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 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.

9. Fattoria di Vegi

Castellina in Chianti

"This property has been under renovation for the past few years, with about another year of construction still to go. They are transforming an old winery into what will eventually be a 5- or 6-star resort, complete with a spa and other amenities. We stayed for two nights with our 11- and 13-year-olds and booked a family suite. The master bedroom bed was extremely comfortable, and the kids’ fold-out bed was large and surprisingly comfortable as well. The bathroom was brand new and had a door...

Brian

NZ$534

includes taxes & fees

24 Aug - 25 Aug

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."

10. Four Points by Sheraton Siena

Scacciapensieri

Raul

NZ$291

includes taxes & fees

1 Sept - 2 Sept

A stone building with a swimming pool, surrounded by trees and a view of the landscape.

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

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.

11. Relais la Costa - Dimora Storica

Monteriggioni

Roberto Javier Sanz

NZ$404

includes taxes & fees

3 Sept - 4 Sept

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

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.

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

12. Sangallo Park Hotel

Vico Alto

Linda

NZ$206

includes taxes & fees

28 Aug - 29 Aug

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

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

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

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

13. Locanda le Piazze

Castellina in Chianti

Oluwafunmilayo

NZ$719

includes taxes & fees

29 Aug - 30 Aug

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

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

14. Hotel Executive

Scacciapensieri

Susan

NZ$178

includes taxes & fees

23 Aug - 24 Aug

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

15. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

NZ$336

includes taxes & fees

23 Aug - 24 Aug

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

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

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.

16. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Qingwen

NZ$968

includes taxes & fees

26 Aug - 27 Aug

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

A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

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

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

17. Hotel Palazzo San niccolò & Spa

Radda in Chianti

gary

NZ$250

includes taxes & fees

24 Aug - 25 Aug

An outdoor dining area with a pool, potted plants, and umbrellas.

A restaurant with a table set for two, overlooking a scenic landscape.

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

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

18. Relais Vignale & Spa

Radda in Chianti

Maaya

NZ$425

includes taxes & fees

27 Aug - 28 Aug

The entrance to a hotel with a sign reading "HOTEL ITALIA". There are two receptionists standing at the reception desk.

A hotel room with a bed, a TV, a dining area with a table and chairs, and a view of the outside.

A bar area with a white countertop, clear chairs, and shelves of liquor bottles.

A breakfast buffet with various food items, a coffee station, and a large mirror on the wall.

19. Hotel Italia

Camollia

Khoon

NZ$194

includes taxes & fees

31 Aug - 1 Sept

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

A large, historic building with a covered patio and a well-maintained garden.

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

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

20. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

NZ$430

includes taxes & fees

23 Aug - 24 Aug

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Top San Leonino Hotel Reviews

Recent Reviews in San Leonino

Hotel Chiusarelli

8/10 Good

"The hotel itself was very nice. The staff were super helpful and we enjoyed our time. The AC and wifi were both a little weak, but otherwise, it was a pleasant stay. The breakfast buffet was also very good with a large selection."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"

Villa Casagrande Resort & SPA

10/10 Excellent

"A beautiful hotel in a lovely little town. The staff were amazing, so helpful. The rooms were very clean and comfortable. I didn’t use the indoor pool or spa facilities so can’t comment on them. The outdoor pool is across the road and up a steep hill, so great if you have a car but not so much if you are on foot! Overall a very good stay."

Hotel Athena

10/10 Excellent

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

La Certosa di Pontignano

10/10 Excellent

"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

Hotel Toscana Ambassador

10/10 Excellent

"Room was clean, staff was helpful and easy to park."

More cheap accommodation in San Leonino

Cannon d'Oro

Via Montanini 28 Siena SI

NZ$164

23 Aug - 24 Aug

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

NZ$192

22 Aug - 23 Aug

includes taxes & fees

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

NZ$193

23 Aug - 24 Aug

includes taxes & fees

8.8/10 Excellent! (104 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

NZ$199

22 Aug - 23 Aug

includes taxes & fees

10/10 Exceptional! (48 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

NZ$331

24 Aug - 25 Aug

includes taxes & fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

Frequently asked questions

What is the best area to stay in San Leonino?

The best area to stay in San Leonino is within the village itself or in the immediate countryside surrounding it.San Leonino is a small village, and staying directly in the village offers the convenience of walking to its few local shops and trattorias. The village is compact, with its main church, Pieve di San Leonino, as a central point of reference, and is surrounded by rolling vineyards and olive groves.For couples seeking a romantic and secluded retreat, staying in one of the agriturismos or boutique hotels just outside the village is ideal. These properties often feature stunning views of the Tuscan landscape, offer cooking classes, and provide a peaceful base from which to explore the Chianti region by car. Many have excellent restaurants on-site, superb for quiet evenings.Travellers looking for a more independent experience will find excellent villa rentals in the countryside around San Leonino. These often come with private pools and well-equipped kitchens, making them superb for those who enjoy cooking with local produce and settling into a home-away-from-home.

When is the best time to go to San Leonino?

The best time to visit San Leonino, Tuscany, is during the spring (April to June) and autumn (September to October) months.During these periods, the weather is pleasantly warm and sunny, making it ideal for exploring the rolling hills and vineyards. You'll find fewer crowds compared to the peak summer months, allowing for a more relaxed experience at local wineries and historic sites. The landscape is particularly beautiful in spring with wildflowers in bloom, and in autumn with the rich colours of the grape harvest.Couples looking for a romantic escape will find these seasons perfect. You can enjoy long walks through the countryside, intimate al fresco dining, and wine-tasting experiences without the intense summer heat or the chill of winter. It's a great time for leisurely drives along scenic routes like the Chiantigiana Road, stopping at charming villages along the way.For travellers interested in culinary experiences, autumn is particularly rewarding. This is the time for grape harvesting and olive oil production, offering opportunities for special tours and tastings.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in San Leonino.

How can I save on a hotel booking in San Leonino with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on San Leonino hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in San Leonino?

Prices for hotels in San Leonino often vary, but you can find a great deal from NZ$147 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

Explore a world of travel with Expedia

Book Hotels in San Leonino on Expedia.it

Search San Leonino hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leonino

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for San Leonino hotels

1. Belvedere di San Leonino

2. Hotel Casafrassi

3. La Certosa di Pontignano

4. Dievole Wine Resort

5. Agriturismo San Sano

6. Hotel Colle Etrusco Salivolpi

7. Palazzo Squarcialupi

8. Hotel Il Piccolo Castello

9. Fattoria di Vegi

10. Four Points by Sheraton Siena

11. Relais la Costa - Dimora Storica

12. Sangallo Park Hotel

13. Locanda le Piazze

14. Hotel Executive

15. Palazzo Leopoldo Dimora Storica & Spa

16. Borgo Scopeto Wine & Country Relais

17. Hotel Palazzo San niccolò & Spa

18. Relais Vignale & Spa

19. Hotel Italia

20. Villa Scacciapensieri Boutique Hotel

Top San Leonino Hotel Reviews

Recent Reviews in San Leonino

Hotel Chiusarelli

Grand Hotel Continental Siena – Starhotels Collezione

Villa Casagrande Resort & SPA

Hotel Athena

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Castello di Leonina Relais

Hotel Toscana Ambassador

More cheap accommodation in San Leonino

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

Explore a world of travel with Expedia

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