Book The Best Hotels in San Leolino for 2026 from CA $76 - Fully Refundable Options

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for San Leolino hotels

A spacious lobby with a reception desk, seating area, and a large vase.

1. Hotel Valdarno

Montevarchi

Emmanuel

CA $175 total

includes taxes & fees

Nov 8 - Nov 9

A buffet with various food items and utensils.

2. Hotel Il Viandante

Terranuova Bracciolini

jessica

CA $174 total

includes taxes & fees

Nov 15 - Nov 16

A person pouring a liquid from a bottle into a glass.

3. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

CA $172 total

includes taxes & fees

Nov 8 - Nov 9

A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.

4. Delta Hotel

Montevarchi

weixing

CA $186 total

includes taxes & fees

Nov 10 - Nov 11

A stone building with multiple windows and a central entrance.

5. Fondaco del Moro

Civitella in Val di Chiana

Heather

CA $103 total

includes taxes & fees

Nov 8 - Nov 9

A dining area with a table and chairs, a view of a landscape through an arched window, and a large umbrella providing shade.

6. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

CA $425 total

includes taxes & fees

Nov 8 - Nov 9

A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.

7. Il Gentiluomo Hotel & SPA

Arezzo

Luis Mauricio

CA $121 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with outdoor seating and a pool in the background.

8. B&B Country House Poggio del Drago

Civitella in Val di Chiana

Kristen

CA $159 total

includes taxes & fees

Nov 13 - Nov 14

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

9. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

CA $106 total

includes taxes & fees

Nov 9 - Nov 10

A spa area with a stone ceiling, a pool, and two sun loungers.

10. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

CA $122 total

includes taxes & fees

Dec 1 - Dec 2

A bedroom with a stone wall, a bed, a nightstand, a window, and a mirror.

11. Casale La Gora

Figline e Incisa Valdarno

Roberto

CA $107 total

includes taxes & fees

Nov 8 - Nov 9

A courtyard with stone flooring, arched walkways, and a central fountain.

12. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

CA $155 total

includes taxes & fees

Dec 8 - Dec 9

A narrow street with buildings on either side, a flag, and a bench.

13. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

CA $174 total

includes taxes & fees

Dec 1 - Dec 2

A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

14. Hotel Le Capanne

Arezzo

Ronilynn

CA $173 total

includes taxes & fees

Nov 30 - Dec 1

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

Bucine

David

CA $380 total

includes taxes & fees

Dec 8 - Dec 9

A modern building with a sign reading "Palace Hotel."

16. Palace Hotel Due Ponti

Due Ponti

Adam

CA $124 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor patio area with wicker furniture, a table, and a lamp.

17. Il Monte

Monte San Savino

Thomas

CA $136 total

includes taxes & fees

Nov 23 - Nov 24

A modern lobby with a bar area, seating, and a large window.

18. Hotel Toscana

Figline e Incisa Valdarno

Anonymous traveller

CA $194 total

includes taxes & fees

Dec 8 - Dec 9

A table set for dining with a scenic view of rolling hills and distant mountains.

19. Castello di Leonina Relais

Asciano

Brooke

CA $113 total

includes taxes & fees

Dec 3 - Dec 4

A modern interior with a piano, dining area, and a large decorative animal statue.

20. B&B Hotel Arezzo

Arezzo

fabio

CA $133 total

includes taxes & fees

Dec 8 - Dec 9

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top San Leolino Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"We loved our stay,"

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"Charming, beautifully decorated, and pet-friendly hotel We enjoyed our stay at this charming hotel. It is very cutely decorated and has lots of character. The location is great if you prefer staying outside the busy city center while still having convenient access to everything. The room was a good size—not too big or too small—with a comfortable bed and a spacious bathroom. Breakfast was also very good, offering everything you need to start the day. Another big plus is that the hotel is pet-friendly! If I had to mention anything, it would be a few minor finishing details, such as the AC vents, that seemed a little unfinished. Nothing major, just small touches that could make the overall experience even better. Overall, a lovely hotel with charm, comfortable rooms, and a welcoming atmosphere. We would happily stay again!"

Il Chiostro del Carmine

8/10 Good

"The location was excellent, within walking distance to all the sights but far enough that it was quiet. Breakfast was excellent and if you can get window seating, it will make a perfect start of the day. The staff was helpful but remains in the background unless you need something. The room was clean, only caveat is the shower is rather small for such a big bathroom. We will stay here again."

Borgo Vescine

10/10 Excellent

"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"

More cheap stays in San Leolino

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

CA $64

CA $76 total

Nov 9 - Nov 10

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 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 $76 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.

Explore a world of travel with Expedia

Book Hotels in San Leolino on Expedia.it

Find hotels in San Leolino from CA $76

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in San Leolino

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for San Leolino hotels

1. Hotel Valdarno

2. Hotel Il Viandante

3. Moody smart & comfy Hotel

4. Delta Hotel

5. Fondaco del Moro

6. Chapter Chianti, a Member of Design Hotels

7. Il Gentiluomo Hotel & SPA

8. B&B Country House Poggio del Drago

9. La Certosa di Pontignano - Place of Charme

10. Hotel Palazzo San niccolò & Spa

11. Casale La Gora

12. Villa Casagrande Resort & SPA

13. Palazzo Leopoldo Dimora Storica & Spa

14. Hotel Le Capanne

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

16. Palace Hotel Due Ponti

17. Il Monte

18. Hotel Toscana

19. Castello di Leonina Relais

20. B&B Hotel Arezzo

Top San Leolino Hotel Reviews

Fattoria di Vegi

More cheap stays in San Leolino

Hotel Chenno

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app