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Sep 23 - Sep 24
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Sep 24 - Sep 25
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Sep 25 - Sep 27
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Oct 2 - Oct 4

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Our top choices for San Leonino hotels

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 rustic stone building with a garden in front.
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.

1. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
Canada
Els
CA $175
CA $202 total
includes taxes & fees
Oct 15 - Oct 16
Belvedere di San Leonino
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.
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.

2. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
United States
Rita
CA $86
CA $105 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Casafrassi
A narrow stone pathway leading to a rustic building with a wooden door and a window.
A well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.
A cozy living room with a fireplace, wooden beams, and comfortable seating.
A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.

3. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
India
Saion
CA $282
CA $317 total
includes taxes & fees
Oct 18 - Oct 19
Castello di Fonterutoli Wine Resort
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 interior corridor with arches, columns, and a brick wall.
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

4. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Roberto
CA $141
CA $168 total
includes taxes & fees
Oct 19 - Oct 20
La Certosa di Pontignano
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 stone building with a wooden bench outside.
A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

5. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
United States
Monica
CA $162
CA $183 total
includes taxes & fees
Oct 21 - Oct 22
Hotel Colle Etrusco Salivolpi
A building with a stone facade, a central arched doorway, and a window with a decorative frame.
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.
A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

6. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
Canada
Marissa
CA $499
CA $562 total
includes taxes & fees
Oct 14 - Oct 15
Dievole Wine Resort
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.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

7. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
Sweden
Sanja
CA $214
CA $249 total
includes taxes & fees
Oct 19 - Oct 20
Castello di Tornano Wine Resort
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 circular hot tub, a window, and a bench.
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

Palazzo Squarcialupi
Castellina in Chianti
United States
yvette
CA $282
CA $320 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
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 building with a paved entrance and a well-maintained garden with potted plants.
A stone wall with a rustic stone building partially visible behind it.

9. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
United States
Ashley
CA $221
CA $251 total
includes taxes & fees
Oct 22 - Oct 23
Relais la Costa - Dimora Storica
A person sitting in a corner of a room with tiled walls and a bench.
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.
A poolside area with lounge chairs, umbrellas, and a swimming pool.

10. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
Canada
Frank
CA $200
CA $231 total
includes taxes & fees
Sep 28 - Sep 29
Hotel Il Piccolo Castello
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.

11. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Ali
CA $236
CA $309 total
includes taxes & fees
Oct 23 - Oct 24
Relais Vignale & Spa
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.

12. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
Canada
Raman
CA $202
CA $234 total
includes taxes & fees
Oct 23 - Oct 24
Hotel Borgo San Luigi
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
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.

13. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
United States
Krishna
CA $257
CA $292 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Villa Campomaggio
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 hotel entrance with a sign reading "HOTEL EXPO".
A modern living room with a glass coffee table, white sofas, and decorative plants.

14. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Susan
CA $114
CA $133 total
includes taxes & fees
Oct 12 - Oct 13
Hotel Executive
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 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."

15. Four Points by Sheraton Siena

Four Points by Sheraton Siena
Scacciapensieri
Australia
Raul
CA $236
CA $267 total
includes taxes & fees
Oct 21 - Oct 22
Four Points by Sheraton Siena
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 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.

16. Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
Canada
Tara
CA $489
CA $548 total
includes taxes & fees
Oct 18 - Oct 19
Locanda le Piazze
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 courtyard with outdoor seating, stone walls, and a staircase.
A buffet area with various fruits and a bar with bottles.

17. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
United States
Afeefa
CA $213
CA $244 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Palazzo San niccolò & Spa
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 large, historic building with a covered patio and a well-maintained garden.
A room with a large window offering a view of a landscaped garden with trees and a pathway.

18. Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel
Scacciapensieri
United Kingdom
Nigel
CA $243
CA $275 total
includes taxes & fees
Oct 24 - Oct 25
Villa Scacciapensieri Boutique Hotel
An outdoor dining area with wicker chairs, a table set with a bowl of chips, a wine glass, and a menu.
A hotel room with a bed, two chairs, a window with a view of a cityscape, and a radiator.
A building with a red and white facade, a balcony with a blue flag, and a red awning over the entrance.
A view through a window with a metal frame, featuring a historic building with a dome and a tall tower.

19. Villa Elda Boutique Hotel

Villa Elda Boutique Hotel
San Prospero
United States
Brian
CA $175
CA $201 total
includes taxes & fees
Oct 22 - Oct 23
Villa Elda Boutique Hotel
An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.
A room with a sofa, a desk, a bunk bed, and a patterned floor.
A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.
A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

20. Villa San Lucchese

Villa San Lucchese
Poggibonsi
United States
Simona
CA $176
CA $203 total
includes taxes & fees
Oct 2 - Oct 3
Villa San Lucchese
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Top San Leonino Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"
Christian 2-night trip
Posted 23 hours ago
Hotel Chiusarelli
Poderi Arcangelo

Poderi Arcangelo

10/10 Excellent
"Location is beautiful. We were in the separate house."
Guillermo 3-night trip
Posted 2 days ago
Poderi Arcangelo
Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Lovely historic hotel, certainly captured the essence of the period it was built in. Room was spacious, beds very comfortable and considering the average temp was 35 degrees for the 3 nights we stayed, the air conditioning worked well enough. C The"
Mark 3-night trip
Posted 3 days ago
Palazzo Ravizza
NH Siena

NH Siena

10/10 Excellent
"El hotel está fuera de las murallas de la ciudad, fuera de la zona restringida para autos, pero cerca de las atracciones de la parte histórica de la ciudad."
Hugo 1-night trip
Posted 4 days ago
NH Siena
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"This resort was simply beautiful! We stayed in the grand room as there were 5 of us, and it was much bigger than I expected! Three bedrooms, 3 washrooms, huge living room - it was great! As we had 2 kids, we had to use the family pool, which was conveniently close to our room. No bar at the pool, but there was a QR code to order drinks and food. There were towels at the pool as well. The staff were very kind and helpful. We appreciated the welcome gift of wine, juice, and snacks too! The breakfast buffet was lovely with lots of variety of hot and cold items. Would highly recommend this resort."
Geeta 1-night trip
Posted 4 days ago
Borgo Scopeto Wine & Country Relais
Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem."
Federica 1-night trip
Posted 7 days ago
Villa Scacciapensieri Boutique Hotel
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks were also brilliant - best meal we had in Tuscany was in the hotel. My only suggestions would be to rotate the staff more - they seemed slightly over worked. Easily one of the best hotels I have stayed in."
David 4-night trip
Posted 7 days ago
Fattoria di Vegi
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"
Roberto 2-night trip
Posted 7 days ago
La Certosa di Pontignano
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good
"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."
Lilianne 2-night trip
Posted 7 days ago
Grand Hotel Continental Siena – Starhotels Collezione

More cheap stays in San Leonino

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
CA $134
CA $155 total
Sep 30 - Oct 1
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
CA $149
CA $172 total
Sep 27 - Sep 28
includes taxes & fees
7.8/10 Good! (439 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
CA $172
CA $197 total
Sep 24 - Sep 25
includes taxes & fees
8.8/10 Excellent! (108 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
CA $215
CA $244 total
Sep 30 - Oct 1
includes taxes & fees
10/10 Exceptional! (49 reviews)
Torre del Fuggisole
Antico Borgo Poggiarello

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI
CA $244
CA $273 total
Oct 11 - Oct 12
includes taxes & fees
9/10 Wonderful! (20 reviews)
Antico Borgo Poggiarello
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

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, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 much is the nightly rate at a San Leonino hotel?
Prices for hotels in San Leonino often vary, but you can find a great deal from CA $98 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 the cheapest rate.

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