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Check prices for these dates

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

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Our top choices for San Leolino hotels

Garden

Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (140 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is CA $124
CA $144 total
includes taxes & fees
Jul 19 - Jul 20
Villa Montarioso
Deluxe Double Room, Balcony

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (43 reviews)
"One of our favorite stays in Italy! Few number of rooms which makes it feel very relaxing and comfortable. Staff was friendly and helpful."
Canada
Yael
The price is CA $166
CA $191 total
includes taxes & fees
Jul 15 - Jul 16
Hotel Ristorante La Dama nella Vigna
Reception

Hotel Borgo Antico

Hotel Borgo Antico
3.0 star property
Monteroni d'Arbia
8.8 out of 10, Excellent, (99 reviews)
"A hidden gem on the Via Francigena. We loved our stay after a day of walking from Siena. Delicious food too. "
United Kingdom
Charles
The price is CA $110
CA $129 total
includes taxes & fees
Jun 28 - Jun 29
Hotel Borgo Antico
Restaurant

Chapter Chianti

Chapter Chianti
5.0 star property
Cavriglia
The price is CA $471
CA $527 total
includes taxes & fees
Jul 13 - Jul 14
Chapter Chianti
Exterior

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (96 reviews)
"This place is amazing. Wonderful drive to the hotel and the solitude is so great. The breakfast was amazing. Staff was very friendly for our stay. Definitely go back."
Canada
Shawn
The price is CA $166
CA $190 total
includes taxes & fees
Jun 28 - Jun 29
Agriturismo San Sano
Exterior

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (51 reviews)
"Beautiful setting, felt like we were staying in a castle! The beds were comfortable and the property was amazing. Highly recommend this place."
Canada
Heather
The price is CA $99
CA $109 total
includes taxes & fees
Jun 24 - Jun 25
Fondaco del Moro
Garden

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very good, (60 reviews)
"A little far away from Siena, but buses came by regularly and taxi's only cost about 12 Euros to get you to and from Siena."
United States
Jack
The price is CA $118
CA $137 total
includes taxes & fees
Jul 4 - Jul 5
Palace Hotel Due Ponti
Outdoor dining

Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (122 reviews)
"Amazing hotel with beautiful territory"
United States
Igor
Palagina la cascina
Snack bar

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (546 reviews)
"Amazing property, loved staying there. Huge rooms, AC worked well, beautiful setting. It’s well worth your time to stay there"
United States
Ken
The price is CA $205
CA $239 total
includes taxes & fees
Jun 29 - Jun 30
La Certosa di Pontignano
Seasonal outdoor pool

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (393 reviews)
"The hotel is beautiful."
United States
Ruth
The price is CA $278
CA $305 total
includes taxes & fees
Jul 5 - Jul 6
Castello Vicchiomaggio
Exterior

Hotel Casafrassi Wine Resort

Hotel Casafrassi Wine Resort
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (222 reviews)
"Incredible place to stay in the Chianti region. Beautiful grounds, amazing food, clean and comfortable rooms, and incredible staff. Location was perfect too! "
United States
Alex
The price is CA $75
CA $109 total
includes taxes & fees
Jun 28 - Jun 29
Hotel Casafrassi Wine Resort
Outdoor dining

Palazzo di Valli

Palazzo di Valli
3.0 star property
Siena
9.6 out of 10, Exceptional, (424 reviews)
"We had a blast, and the proprietors were fantastic. They had plenty of local knowledge and seemed to have a real passion for what they do. Plus the venue is wonderful, and they have the best patio with views of the Tuscan hills. Would recommend, and would stay again."
United States
John
The price is CA $158
CA $182 total
includes taxes & fees
Jul 15 - Jul 16
Palazzo di Valli
2 outdoor pools

Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
Podere L'Aquila
Sauna, hot tub, steam room, Turkish bath, body treatments

Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
4.0 star property
Arezzo
8.6 out of 10, Excellent, (158 reviews)
"3 star hotel only"
Canada
David Joseph
The price is CA $86
CA $105 total
includes taxes & fees
Jul 8 - Jul 9
Il Gentiluomo Hotel & SPA
Front of property

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
The price is CA $325
CA $371 total
includes taxes & fees
Jul 12 - Jul 13
Castello di Tornano Wine Resort
Lobby lounge

Antico Granaione

Antico Granaione
Rapolano Terme
10.0 out of 10, Exceptional, (61 reviews)
"old fashion building, clean and affordable"
United States
Irene
The price is CA $133
CA $153 total
includes taxes & fees
Jul 5 - Jul 6
Antico Granaione
Sundeck

Hotel Palazzo dei Priori

Hotel Palazzo dei Priori
4.0 star property
Siena
8.8 out of 10, Excellent, (419 reviews)
"Staff very helpful, hotel was fine but very dated. The bathroom felt a little bit grubby. Had a few issues with the keys which were eventually solved, but no major problems. Good location, near to a major bus stop to go into central Siena. It’s worth noting that buses are quite unreliable in the evening so you may have to get a taxi back to the hotel (10-12 euros ish)."
United Kingdom
Louisa
The price is CA $96
CA $128 total
includes taxes & fees
Jun 24 - Jun 25
Hotel Palazzo dei Priori
Property entrance

Hotel I Platani

Hotel I Platani
3.0 star property
Monteriggioni
8.8 out of 10, Excellent, (185 reviews)
"The staff was wonderful. Immensely nice person who made sure we had a safe, good time!!"
United States
Ann
The price is CA $118
CA $138 total
includes taxes & fees
Jun 28 - Jun 29
Hotel I Platani
Lobby sitting area

Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio
3.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (206 reviews)
"Amazing experience in nature and cozy atmosphere, breakfast is super, restaurant as well. "
Netherlands
OY
The price is CA $105
CA $121 total
includes taxes & fees
Jul 5 - Jul 6
Hotel Tenuta Il Burchio
Breakfast, lunch, dinner and brunch served

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (133 reviews)
"Really enjoyed our stay, clean room and property. Very quiet place with a nice pool."
Canada
Meghan
The price is CA $269
CA $305 total
includes taxes & fees
Jul 1 - Jul 2
Castello di Leonina Relais
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.
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Top San Leolino Hotel Reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"I would absolutely recommend Castello Vicchiomaggio! Our room was magnificent and much larger than anticipated— very clean, had all the extras we needed (hair dryer/iron/etc), and the air conditioning worked great! The property is gorgeous and the view is unbeatable. In addition to visiting the tasting room on the property, we also visited several wineries in the area throughout our stay (Antinori and Castello Verrazzano) and it was a great home base. We enjoyed dinner at the restaurant one night (delicious!) and the included breakfast was a great perk. The pool area is also very nice and they provided a pool bag and extra towels in our room to use there. We were also very charmed by the sweet cat that lives on the grounds and the birds (house martins) that were in the area during the time of our stay! The staff was always helpful and kind— I have nothing but great things to say. One warning: our room was on the third floor of the building and there are no elevators. Luckily my husband was with me and able to haul our luggage up the tight stairs. If you have mobility issues, I would recommend asking for a room on a lower floor."
Taylor 2-night trip
Posted 23 hours ago
Castello Vicchiomaggio

More cheap stays in San Leolino

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI
The price is CA $75 per night from Jun 24 to Jun 25
CA $75
CA $88 total
Jun 24 - Jun 25
includes taxes & fees

Frequently asked questions

What is the best area to stay in San Leolino?
When visiting San Leolino, the best area to stay is within the hamlet itself or in the immediately surrounding countryside, particularly towards the charming town of Castellina in Chianti.

The hamlet of San Leolino itself is very small, centred around its historic Romanesque church, Pieve di San Leolino. Staying directly within the hamlet or in a nearby villa allows for a truly tranquil experience, surrounded by rolling vineyards and olive groves. It's a place where you can enjoy the quiet beauty of the Tuscan landscape, often with stunning views across the valley.

Couples seeking a romantic and peaceful escape will find the immediate vicinity of San Leolino perfect. Many accommodations here are renovated farmhouses or boutique properties that offer privacy, beautiful scenery, and opportunities for wine tasting at nearby vineyards. You'll often find properties with private pools and terraces, ideal for enjoying a glass of Chianti while watching the sunset.

Families might prefer staying in a villa or agriturismo slightly closer to Castellina in Chianti, which is just a short drive away. This offers the same peaceful setting but with easier access to amenities like grocery shops, restaurants, and a few local artisan stores in Castellina's historic centre.
When is the best time to go to San Leolino?
The best times to visit San Leolino are typically in the spring (April to early June) and autumn (September to October) when the weather is pleasant and the region is less crowded.

For those looking for comfortable temperatures for exploring the Tuscan countryside, spring offers mild weather, often with blooming wildflowers. The days are generally sunny without being overly hot, making it ideal for walking through vineyards or visiting nearby towns like Siena or Florence. You'll also find fewer tourists compared to the peak summer months.

Autumn provides a similar experience with comfortable temperatures, and it's also harvest season. This is a lovely time for food and wine enthusiasts, as many local farms and vineyards offer special experiences.
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 Leolino.
How can I save on a San Leolino hotel booking with Expedia?
Members always get our best prices. Find our best San Leolino hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a San Leolino hotel?
Prices for hotels in San Leolino often vary, but you can find a great deal from CA $88 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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