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Our top choices for San Leonino hotels

1. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (190 reviews)
"Very clean and amazing staff. And the room is at such a nice and rich location with a beautiful view."
United States
Christopher
The price is AU$207
includes taxes & fees
9 Aug - 10 Aug
Belvedere di San Leonino

2. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (229 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 AU$114
includes taxes & fees
2 Aug - 3 Aug
Hotel Casafrassi

3. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (551 reviews)
"Everything was perfect!"
United States
Edyta
The price is AU$161
includes taxes & fees
23 Aug - 24 Aug
La Certosa di Pontignano

4. Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (101 reviews)
"A wonderful property with friendly employees! Did not want to leave!"
United States
Paula
The price is AU$151
includes taxes & fees
2 Aug - 3 Aug
Agriturismo San Sano

5. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (203 reviews)
"The property and location is amazing! The on site amenities are outstanding. The infinity pool has a beautiful view. The wine tasting and tour experience was exceptional. The restaurant for breakfast and dinner is also exceptional. The entire staff at the resort were friendly, and extremely helpful !"
United States
Rory
The price is AU$509
includes taxes & fees
26 Aug - 27 Aug
Dievole Wine Resort

6. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (123 reviews)
"Friendly staff and walking distance to town"
United States
Scott
The price is AU$195
includes taxes & fees
9 Aug - 10 Aug
Hotel Colle Etrusco Salivolpi

7. Palazzo Squarcialupi

Palazzo Squarcialupi
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"We stayed for a week and loved everything about this hotel. The staff went out of their way to make sure everything was perfect and everyone was so friendly. We really enjoyed breakfast each morning on the terrace and we used the pool and spa every day. Very relaxing and walking distance to everything in Castellina. Their pasta restaurant located across the street is also very good."
United States
Jennifer
The price is AU$354
includes taxes & fees
31 July - 1 Aug
Palazzo Squarcialupi

8. Four Points by Sheraton Siena

Four Points by Sheraton Siena
4.0 star property
Scacciapensieri
8.8 out of 10, Excellent, (599 reviews)
"Yes,breakfast menu was fresh. Parking area felt safe and convenient."
Canada
Keith
The price is AU$242
includes taxes & fees
20 Aug - 21 Aug
Four Points by Sheraton Siena

9. Hotel Executive

Hotel Executive
4.0 star property
Scacciapensieri
8.4 out of 10, Very good, (545 reviews)
"Nice clean hotel. Breakfast ok. Good parking"
United Kingdom
Susan
The price is AU$107
includes taxes & fees
6 Aug - 7 Aug
Hotel Executive

10. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
4.0 star property
Monteriggioni
8.8 out of 10, Excellent, (355 reviews)
"Clean, functional, the breakfast very good "
United Kingdom
Ian
The price is AU$240
includes taxes & fees
2 Aug - 3 Aug
Hotel Il Piccolo Castello

11. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
9.6 out of 10, Exceptional, (79 reviews)
"Whole place felt amazing, staff was super! Def recommend!"
United States
Roberto Javier Sanz
The price is AU$260
includes taxes & fees
2 Aug - 3 Aug
Relais la Costa - Dimora Storica

12. Hotel Le Fontanelle

Hotel Le Fontanelle
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (110 reviews)
"Beautiful place and wonderful staff. Would recommend!"
United States
Malcolm
The price is AU$525
includes taxes & fees
30 Aug - 31 Aug
Hotel Le Fontanelle

13. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (294 reviews)
"very well maintained hotel with friendly staff"
United States
Lin
The price is AU$252
includes taxes & fees
4 Aug - 5 Aug
Palazzo Leopoldo Dimora Storica & Spa

14. Sangallo Park Hotel

Sangallo Park Hotel
3.0 star property
Vico Alto
9.0 out of 10, Wonderful, (617 reviews)
"Great hotel extremely helpful staff"
United Kingdom
Linda
The price is AU$157
includes taxes & fees
30 Aug - 31 Aug
Sangallo Park Hotel

15. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (194 reviews)
"Everything was awesome, the hotel staff was very helpful and friendly."
United States
gary
The price is AU$200
includes taxes & fees
23 Aug - 24 Aug
Hotel Palazzo San niccolò & Spa

16. Hotel Palazzo dei Priori

Hotel Palazzo dei Priori
4.0 star property
Siena
8.8 out of 10, Excellent, (424 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 AU$160
includes taxes & fees
3 Aug - 4 Aug
Hotel Palazzo dei Priori

17. Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (351 reviews)
"Beautiful place to spend your time while discovering Tuscany."
United States
Simona
The price is AU$199
includes taxes & fees
31 July - 1 Aug
Villa San Lucchese

18. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (217 reviews)
"Absolutely wonderful stay. The onsite restaurant was amazing and the staff was very attentive and helpful. There are nice wineries and restaurants nearby too and the concierge made very helpful recommendations and reservations for us. Use the hotel name (and not just the address) since the Apple Maps and Google Maps gets confused otherwise."
United States
Sachin
The price is AU$797
includes taxes & fees
6 Aug - 7 Aug
Borgo Scopeto Wine & Country Relais

19. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
9.8 out of 10, Exceptional, (10 reviews)
"This property has been under renovation for the past few years, with about another year of construction still to go. They are transforming an old winery into what will eventually be a 5- or 6-star resort, complete with a spa and other amenities. We stayed for two nights with our 11- and 13-year-olds and booked a family suite. The master bedroom bed was extremely comfortable, and the kids’ fold-out bed was large and surprisingly comfortable as well. The bathroom was brand new and had a door...
United States
Brian
The price is AU$506
includes taxes & fees
24 Aug - 25 Aug
Fattoria di Vegi

20. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (236 reviews)
"Great place with incredibly helpful staff"
United States
David
The price is AU$809
includes taxes & fees
8 Aug - 9 Aug
Borgo Vescine
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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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 cancelled 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 can I save on a hotel booking in San Leonino with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on San Leonino hotels. Plus, you'll earn OneKeyCashā„¢* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in San Leonino?
Prices for hotels in San Leonino often vary, but you can find a great deal from AU$107 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 our cheapest rates.

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