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Aug 16 - Aug 17
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Aug 17 - Aug 18
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Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

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Our top choices for San Leolino hotels

Lunch and dinner served
Outdoor wedding area
Indoor wedding
Aerial view

1. Il Verreno

Il Verreno
Ambra
United Kingdom
Ji Young
CA $359
CA $401 total
includes taxes & fees
Aug 20 - Aug 21
Il Verreno
Continental breakfast for a fee
Lobby
Property entrance
Terrace/patio

2. Hotel Il Viandante

Hotel Il Viandante
Terranuova Bracciolini
United States
Michelle
CA $137
CA $183 total
includes taxes & fees
Aug 17 - Aug 18
Hotel Il Viandante
Reception
Bar (on property)
Property entrance
Minibar, in-room safe, desk, blackout drapes

3. Hotel Valdarno

Hotel Valdarno
Montevarchi
United States
Emmanuel
CA $154
CA $169 total
includes taxes & fees
Aug 22 - Aug 23
Hotel Valdarno
Snack bar
Exterior detail
Terrace/patio
Breakfast, lunch and dinner served

4. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Edyta
CA $93
CA $116 total
includes taxes & fees
Sep 8 - Sep 9
La Certosa di Pontignano
Exterior
1 bedroom, Frette Italian sheets, premium bedding, memory foam beds
Deluxe Apartment, 1 Bedroom | Private kitchen
Reception

5. Delta Hotel

Delta Hotel
Montevarchi
United States
weixing
CA $152
CA $168 total
includes taxes & fees
Aug 26 - Aug 27
Delta Hotel
Exterior
Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas
Exterior
Terrace/patio

6. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
United States
Paula
CA $195
CA $221 total
includes taxes & fees
Aug 27 - Aug 28
Agriturismo San Sano
Daily buffet breakfast for a fee
2 outdoor pools
Front of property
Lavender | Living area

7. Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
CA $236
CA $657 total
includes taxes & fees
Aug 23 - Aug 24
Podere L'Aquila
Front of property
Front of property
Aerial view
Land view from property

8. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Austin
CA $310
CA $354 total
includes taxes & fees
Aug 24 - Aug 25
Castello di Tornano Wine Resort
Exterior
Down comforters, minibar, in-room safe, soundproofing
Restaurant
Restaurant

9. Villa Sassolini Country Boutique Hotel

Villa Sassolini Country Boutique Hotel
Montevarchi
United Kingdom
Peter
CA $387
CA $426 total
includes taxes & fees
Aug 26 - Aug 27
Villa Sassolini Country Boutique Hotel
Restaurant
Restaurant
Outdoor dining
Outdoor pool

10. Palazzo Tiglio - A Small Luxury Hotels of the World

Palazzo Tiglio - A Small Luxury Hotels of the World
Bucine
United States
David
CA $358
CA $400 total
includes taxes & fees
Sep 8 - Sep 9
Palazzo Tiglio - A Small Luxury Hotels of the World
Daily buffet breakfast for a fee
Deluxe Double Room
Outdoor pool, free cabanas, pool umbrellas
Lobby sitting area

11. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
United States
Hannah
CA $218
CA $252 total
includes taxes & fees
Sep 9 - Sep 10
Ultimo Mulino Wellness Country Hotel
In-room safe, blackout drapes, soundproofing, WiFi (free)
Exterior
Garden
In-room safe, blackout drapes, soundproofing, WiFi (free)

12. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
CA $546
CA $610 total
includes taxes & fees
Aug 20 - Aug 21
Chapter Chianti, a Member of Design Hotels
Sauna, hot tub, steam room, Turkish bath, body treatments
Sauna, hot tub, steam room, Turkish bath, body treatments
Sauna, hot tub, steam room, Turkish bath, body treatments
Rooftop terrace

13. Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
Arezzo
United States
Luis Mauricio
CA $100
CA $119 total
includes taxes & fees
Aug 24 - Aug 25
Il Gentiluomo Hotel & SPA
Indoor pool, outdoor pool, sun loungers
Dining
Junior Suite | View from room
Restaurant

14. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
CA $512
CA $580 total
includes taxes & fees
Sep 6 - Sep 7
Castello di Spaltenna- Small Luxury Hotels of the World
Garden
Free daily full breakfast
Courtyard
Premium bedding, down comforters, in-room safe, desk

15. Palace Hotel Due Ponti

Palace Hotel Due Ponti
Due Ponti
United States
borjan
CA $122
CA $142 total
includes taxes & fees
Sep 14 - Sep 15
Palace Hotel Due Ponti
Chapel
Superior Suite, 1 King Bed | Living area
Front of property
Superior Suite, 1 King Bed | Terrace/patio

16. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
United States
Rory
CA $446
CA $503 total
includes taxes & fees
Aug 30 - Aug 31
Dievole Wine Resort
Daily buffet breakfast for a fee
Couples treatment rooms, sauna, hot tub, steam room, Turkish bath
Vineyard view
Lobby

17. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
Canada
Elizabeth
CA $241
CA $274 total
includes taxes & fees
Aug 23 - Aug 24
Palazzo Leopoldo Dimora Storica & Spa
Restaurant
Outdoor pool, sun loungers
Apartment, 2 Bedrooms, Patio (6 Adults) | Living room
House (Il Torrino) | Private kitchen

18. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
United States
Alejandro
CA $172
CA $195 total
includes taxes & fees
Aug 31 - Sep 1
Borgo di Pietrafitta Relais
Outdoor dining
Seasonal outdoor pool, sun loungers
Double Room
Front of property

19. Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
United States
Peter
CA $90
CA $103 total
includes taxes & fees
Aug 27 - Aug 28
Palagina la cascina
Breakfast, lunch and dinner served
Exterior
Exterior
Daily buffet breakfast for a fee

20. Castello di Leonina Relais

Castello di Leonina Relais
Asciano
Canada
Meghan
CA $234
CA $267 total
includes taxes & fees
Sep 7 - Sep 8
Castello di Leonina Relais
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Top San Leolino Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

8/10 Good
"All in all a lovely property with lovely staff. Good location, easy bus ride to Siena town."
Natalia 2-night trip
Posted less than an hour ago
Villa Scacciapensieri Boutique Hotel
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"
C 3-night trip
Posted 2 days ago
Villa Casagrande Resort & SPA
Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It’s a nice enough property, but certainly not four or five star. I did enjoy my stay. The staff were phenomenal. The room was fine. I only was there for one night. The breakfast was so no food at all."
Joseph 1-night trip
Posted 2 days ago
Hotel Chiusarelli
Hotel Athena

Hotel Athena

10/10 Excellent
"Wonderful hotel in great location just a short walk from the centre but quiet and peaceful in the evening. Fabulous helpful staff. Breakfast always fresh and lots of choice. We used the terrace restaurant once and it was fabulous - what amazing views! Highly recommended for a short or longer stay"
Richard 7-night trip
Posted 10 days ago
Hotel Athena
Borgo Scopeto Wine & Country Relais

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."
Nicholas 7-night trip
Posted 11 days ago
Borgo Scopeto Wine & Country Relais
Castello di Spaltenna- Small Luxury Hotels of the World

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"
Ashley 2-night trip
Posted 11 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
La Certosa di Pontignano

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."
Frederic 4-night trip
Posted 12 days ago
La Certosa di Pontignano
Castello di Leonina Relais

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."
Anthony 2-night trip
Posted 2 months ago
Castello di Leonina Relais
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Amazing hotel! Looking forward to coming back."
Harry 2-night trip
Posted 2 months ago
Fattoria di Vegi

More cheap stays in San Leolino

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
CA $133
CA $155 total
Aug 18 - Aug 19
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 $135
CA $156 total
Aug 18 - Aug 19
includes taxes & fees
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
CA $136
CA $158 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (104 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
CA $152
CA $175 total
Aug 18 - Aug 19
includes taxes & fees
10/10 Exceptional! (48 reviews)
Torre del Fuggisole
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
CA $186
CA $338 total
Aug 29 - Aug 30
includes taxes & fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get rates
9.4/10 Exceptional! (23 reviews)
Porta Pispini Residence

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 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 $116 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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