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Our top choices for San Leolino hotels

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (541 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 £126
includes taxes & fees
30 Jun - 1 Jul
La Certosa di Pontignano

Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (192 reviews)
"Beautiful property and very friendly helpful staff"
Canada
Pamela
The price is £287
includes taxes & fees
2 Jul - 3 Jul
Dievole Wine Resort

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
The price is £294
includes taxes & fees
11 Jun - 12 Jun
Fattoria di Vegi

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (92 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 £101
includes taxes & fees
10 Jun - 11 Jun
Agriturismo San Sano

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.2 out of 10, Wonderful, (109 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
The price is £202
includes taxes & fees
23 Jun - 24 Jun
Castello di Tornano Wine Resort

Borgo San Felice Resort

Borgo San Felice Resort
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (84 reviews)
"Absolutely wonderful!"
Canada
Cynthia
The price is £708
includes taxes & fees
5 Jul - 6 Jul
Borgo San Felice Resort

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (41 reviews)
"Great place to stay and visit all the surrounding hill towns! Breakfast was excellent. Daniela took amazing care of us! Will definitely return!"
United States
Norma
The price is £101
includes taxes & fees
6 Jul - 7 Jul
Hotel Ristorante La Dama nella Vigna

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 £73
includes taxes & fees
7 Jun - 8 Jun
Palace Hotel Due Ponti

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (200 reviews)
"Amazing hotel"
United Kingdom
Bogdan
The price is £426
includes taxes & fees
5 Jul - 6 Jul
Borgo Scopeto Wine & Country Relais

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (47 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 £58
includes taxes & fees
8 Jun - 9 Jun
Fondaco del Moro

Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (139 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is £79
includes taxes & fees
5 Jul - 6 Jul
Villa Montarioso

Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
10.0 out of 10, Exceptional, (276 reviews)
"beautiful hotel! staff is so friendly, we had a great time "
United Kingdom
joseph
The price is £304
includes taxes & fees
8 Jun - 9 Jun
Borgo Del Cabreo

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (387 reviews)
"We really enjoyed our stay. It was far too short, but we truly loved the property. The breakfast was lovely as well!"
United States
Tiffany
The price is £188
includes taxes & fees
28 Jun - 29 Jun
Castello Vicchiomaggio

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (285 reviews)
"Great hotel to stay to relax ..."
United States
Thiago
The price is £124
includes taxes & fees
9 Jun - 10 Jun
Palazzo Leopoldo Dimora Storica & Spa

Hotel Borgo Antico

Hotel Borgo Antico
3.0 star property
Monteroni d'Arbia
8.8 out of 10, Excellent, (98 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 £76
includes taxes & fees
5 Jul - 6 Jul
Hotel Borgo Antico

Hotel Le Fontanelle

Hotel Le Fontanelle
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (99 reviews)
"Amazing place to stay in Tuscany!"
United States
Maria
The price is £286
includes taxes & fees
5 Jul - 6 Jul
Hotel Le Fontanelle

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 £111
includes taxes & fees
6 Jul - 7 Jul
Palazzo di Valli

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (164 reviews)
"Our girls loved having the upstairs to themselves, the staff was friendly and helpful, and the breakfast was *delicious!*"
United States
Michelle
The price is £94
includes taxes & fees
5 Jul - 6 Jul
Hotel Il Viandante

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux
Loro Ciuffenna
9.2 out of 10, Wonderful, (103 reviews)
"The views were spectacular along with the food"
United States
cory
The price is £594
includes taxes & fees
16 Jun - 17 Jun
Il Borro - Relais & Châteaux

Il Verreno

Il Verreno
Ambra
9.8 out of 10, Exceptional, (59 reviews)
"I absolutely love this hotel! This is the second year I've stayed here and it's absolutely beautiful, the food is delicious, and the staff is top notch. I highly recommend for anyone who wants to explore beautiful Tuscany."
United States
Marc
The price is £213
includes taxes & fees
1 Jul - 2 Jul
Il Verreno
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

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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 £47 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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