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Our top choices for San Leonino hotels

1. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (581 reviews)
"Great location amazing place"
United States
Rodolfo
The price is CA $85
CA $106 total
includes taxes & fees
Nov 9 - Nov 10
La Certosa di Pontignano - Place of Charme

2. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (211 reviews)
"Brautiful scenery, convenient location. Parking was great."
Canada
Kevork
The price is CA $151
CA $175 total
includes taxes & fees
Nov 12 - Nov 13
Belvedere di San Leonino

3. Sangallo Park Hotel

Sangallo Park Hotel
3.0 star property
Vico Alto
9.0 out of 10, Wonderful, (623 reviews)
"Excellent staff"
United Kingdom
Marcio Tadeu
The price is CA $123
CA $140 total
includes taxes & fees
Nov 15 - Nov 16
Sangallo Park Hotel

4. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (234 reviews)
"The staff and experience staying at Castello Di Fonterutoli was amazing! Everyone was so kind and welcoming! Cannot wait to go back☺️"
United States
Micaela
The price is CA $219
CA $247 total
includes taxes & fees
Nov 9 - Nov 10
Castello di Fonterutoli Wine Resort

5. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (249 reviews)
"Absolutely loved our stay here. The property is beautiful and the staff are lovely. The best value stay we had on our Italy trip. Can hear the horses whilst lying by the pool and the house has a very friendly ginger cat too!"
United Kingdom
Stuart
The price is CA $84
CA $102 total
includes taxes & fees
Nov 18 - Nov 19
Hotel Casafrassi

6. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (198 reviews)
"Great stay!"
United States
Afeefa
The price is CA $102
CA $122 total
includes taxes & fees
Dec 1 - Dec 2
Hotel Palazzo San niccolò & Spa

7. Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (59 reviews)
"Beautiful and excellent. Great stay."
United States
Amanda
The price is CA $141
CA $163 total
includes taxes & fees
Nov 12 - Nov 13
Hotel Ristorante La Dama nella Vigna

8. Hotel Executive

Hotel Executive
4.0 star property
Scacciapensieri
8.4 out of 10, Very good, (557 reviews)
"Nice modern business hotel with spacious rooms. Mine had a balcony too. Plenty of parking on site. I ate in the restaurant which was good and reasonably priced. It’s a bit out of the way, so definitely not somewhere to explore Siena on foot by!"
United Kingdom
Andras
The price is CA $92
CA $106 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Executive

9. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (306 reviews)
"Very helpful and friendly staff, beautiful and spacious room, and wonderful location in the most lovely town in Tuscany. We loved our stay!"
Canada
Elizabeth
The price is CA $149
CA $174 total
includes taxes & fees
Dec 1 - Dec 2
Palazzo Leopoldo Dimora Storica & Spa

10. Four Points by Sheraton Siena

Four Points by Sheraton Siena
4.0 star property
Scacciapensieri
8.8 out of 10, Excellent, (609 reviews)
"Excellent property. It was well maintained, and the staff was friendly. I would definitely stay here again."
United States
Ralph
The price is CA $179
CA $201 total
includes taxes & fees
Nov 20 - Nov 21
Four Points by Sheraton Siena

11. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
4.0 star property
Monteriggioni
8.6 out of 10, Excellent, (369 reviews)
"Good value"
Canada
Frank
The price is CA $157
CA $184 total
includes taxes & fees
Nov 9 - Nov 10
Hotel Il Piccolo Castello

12. Hotel I Platani

Hotel I Platani
3.0 star property
Monteriggioni
8.8 out of 10, Excellent, (186 reviews)
"Very kind staff. "
United States
Jorge
The price is CA $90
CA $107 total
includes taxes & fees
Nov 9 - Nov 10
Hotel I Platani

13. Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.6 out of 10, Excellent, (74 reviews)
"All the staff were very friendly and knowledgeable about the area. Breakfast and the restaurant were delicious as well."
United States
Adam
The price is CA $109
CA $124 total
includes taxes & fees
Nov 16 - Nov 17
Palace Hotel Due Ponti

14. Hotel Villa San Giorgio

Hotel Villa San Giorgio
3.0 star property
Poggibonsi
9.0 out of 10, Wonderful, (116 reviews)
"Very buetifull hotel with magnificent view on Tuscany hills. Very kind staff, clean room and Very good breakfast."
United States
Arik
The price is CA $84
CA $93 total
includes taxes & fees
Nov 15 - Nov 16
Hotel Villa San Giorgio

15. Hotel Borgo San Luigi

Hotel Borgo San Luigi
4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (456 reviews)
"It was definitely a place we will return too."
United States
JOHN
The price is CA $158
CA $185 total
includes taxes & fees
Nov 10 - Nov 11
Hotel Borgo San Luigi

16. Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (238 reviews)
"Place was very clean and close to good food."
Canada
Patricia
The price is CA $109
CA $126 total
includes taxes & fees
Nov 24 - Nov 25
Villa Sabolini

17. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (219 reviews)
"This stay was absolutely perfect. The staff is amazing and we had a great time! The food is also great!"
Norway
Magdalena
The price is CA $367
CA $417 total
includes taxes & fees
Nov 16 - Nov 17
Dievole Wine Resort

18. Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (360 reviews)
"Very nice"
United Kingdom
James
The price is CA $159
CA $174 total
includes taxes & fees
Nov 9 - Nov 10
Villa San Lucchese

19. Relais Castel Bigozzi

Relais Castel Bigozzi
4.0 star property
Monteriggioni
8.8 out of 10, Excellent, (247 reviews)
"Its location only the rest is like the 80"
United States
Nissan
The price is CA $132
CA $156 total
includes taxes & fees
Nov 9 - Nov 10
Relais Castel Bigozzi

20. Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA
4.0 star property
Colle di Val d'Elsa
9.4 out of 10, Exceptional, (475 reviews)
"Beautiful property, spacious and well-appointed room, spa was beautiful and relaxing."
United States
Kerry
The price is CA $145
CA $166 total
includes taxes & fees
Nov 15 - Nov 16
Hotel Palazzo San Lorenzo & SPA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Compare top hotels in San Leonino

Castelnuovo Berardenga
4.0 star property
Castellina in Chianti
3.0 star property
Vico Alto
Castellina in Chianti
4.0 star property
Castellina in Chianti
9.4
Exceptional
581 reviews
9.6
Exceptional
211 reviews
9.0
Wonderful
623 reviews
9.4
Exceptional
234 reviews
8.2
Very good
249 reviews
The price is CA $85
CA $106 total
includes taxes & fees
Nov 9 - Nov 10
The price is CA $151
CA $175 total
includes taxes & fees
Nov 12 - Nov 13
The price is CA $123
CA $140 total
includes taxes & fees
Nov 15 - Nov 16
The price is CA $219
CA $247 total
includes taxes & fees
Nov 9 - Nov 10
The price is CA $84
CA $102 total
includes taxes & fees
Nov 18 - Nov 19
  • No Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • No Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • No Parking
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Top San Leonino Hotel Reviews

More cheap stays in San Leonino

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 $83 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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