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1 Oct - 2 Oct
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2 Oct - 3 Oct
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2 Oct - 4 Oct
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9 Oct - 11 Oct

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Our top choices for San Leolino hotels

A spacious lobby with a reception desk, seating area, and a large vase.
A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.
A hotel room with a large bed, two armchairs, a small table with a tray of breakfast items, a television, and curtains.
A patio with a round table and chairs, potted plants, and a view of the building's interior.

1. Hotel Valdarno

Hotel Valdarno
Montevarchi
United States
Emmanuel
NZ$224
includes taxes & fees
8 Oct - 9 Oct
Hotel Valdarno
A hotel room with a bed, a desk with a laptop, a chair, a nightstand, and a view through the window.
A hotel with a sign reading "Michelangelo HOTEL".
A hotel hallway with a polished floor, wooden doors, and a green exit sign.
A hotel lobby with a reception desk, seating areas, and a dining area.

2. Hotel Michelangelo

Hotel Michelangelo
Terranuova Bracciolini
United States
Sushil
NZ$203
includes taxes & fees
6 Oct - 7 Oct
Hotel Michelangelo
A buffet with various food items and utensils.
A hotel entrance with a sign reading "HOTEL il Viandante".
A modern lobby with a reception desk, two seating areas with orange chairs, and a marble floor.
A hotel room with a large bed, bedside tables, a nightstand, a vase with flowers, a tray with pastries, a teapot, and a glass of orange juice.

3. Hotel Il Viandante

Hotel Il Viandante
Terranuova Bracciolini
United States
Michelle
NZ$206
includes taxes & fees
18 Oct - 19 Oct
Hotel Il Viandante
A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.
A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.
A modern reception area with a wooden reception desk, a metal bowl, potted plants, and a seating area with chairs.
A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

4. Delta Hotel

Delta Hotel
Montevarchi
United States
weixing
NZ$226
includes taxes & fees
7 Oct - 8 Oct
Delta Hotel
A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.
An outdoor dining area with long tables set for a meal, surrounded by greenery and trees.
A poolside area with a swimming pool, lounge chairs, and a grassy lawn.
A long table set for a formal event, with clear chairs and white tablecloths, under a large chandelier and surrounded by greenery.

5. Il Verreno

Il Verreno
Ambra
Canada
Minna
NZ$443
includes taxes & fees
12 Oct - 13 Oct
Il Verreno
A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.
An outdoor dining area with tables and chairs, overlooking a scenic view of a coastal town during sunset.
An indoor dining area with tables set for two, large windows, and potted plants.
A cozy living room with a fireplace, wooden bookshelves, and a decorative mirror.

6. Villa Sassolini Country Boutique Hotel

Villa Sassolini Country Boutique Hotel
Montevarchi
United Kingdom
Peter
NZ$409
includes taxes & fees
18 Oct - 19 Oct
Villa Sassolini Country Boutique Hotel
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A modern living room with a white sofa, armchairs, and a coffee table.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.
A reception area with a wooden ceiling, a reception desk, and seating.

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
NZ$543
includes taxes & fees
6 Oct - 7 Oct
Chapter Chianti, a Member of Design Hotels
A stone building with multiple windows and a central entrance.
A dining area with a table set for two, white chairs, and a stone-patterned floor.
A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.
A terrace with a sofa and cushions, overlooking a cityscape and mountains.

8. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
Canada
Heather
NZ$136
includes taxes & fees
6 Oct - 7 Oct
Fondaco del Moro
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
A historic stone building with a large arched window and a small balcony.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone building with a tower, surrounded by people dining at tables with candles.

9. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Lisa
NZ$295
includes taxes & fees
29 Oct - 30 Oct
Castello di Tornano Wine Resort
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a window and a light fixture.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A pool surrounded by lush greenery and vineyards, with a stone building in the background.

10. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
Australia
Glen
NZ$152
includes taxes & fees
18 Oct - 19 Oct
Agriturismo San Sano
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

11. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
Canada
Samantha
NZ$200
includes taxes & fees
22 Oct - 23 Oct
Ultimo Mulino Wellness Country Hotel
A stone building with outdoor seating and a pool in the background.
A dining table set with various foods, including meats, cheeses, and fruits.
A bedroom with two beds, a chandelier, a leopard-print chair, and a small table with a vase.
A swimming pool with a breakfast tray of fruits and juice, surrounded by trees and a clear sky.

12. B&B Country House Poggio del Drago

B&B Country House Poggio del Drago
Civitella in Val di Chiana
United States
Kristen
NZ$193
includes taxes & fees
11 Oct - 12 Oct
B&B Country House Poggio del Drago
A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.
A hallway with a decorative archway leading to a door, a row of plants on the left, and a wall-mounted lamp on the right.
A modern hotel lobby with a large mirror, potted plants, and a spacious seating area.
A spa area with a circular hot tub surrounded by mosaic tiles, a stone bench, and a small table with a bowl and a candle.

13. Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
Arezzo
United States
Luis Mauricio
NZ$155
includes taxes & fees
11 Oct - 12 Oct
Il Gentiluomo Hotel & SPA
A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.
A stone house with a tiled roof, surrounded by greenery and a gravel path.
A stone-walled room with a sofa, a coat rack, and a window with curtains.
A stone building with a balcony, potted plants, and a view of distant hills.

14. Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
Canada
Heather
NZ$807
includes taxes & fees
6 Oct - 7 Oct
Podere L'Aquila
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.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
An interior corridor with arches, columns, and a brick wall.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

15. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Leslie
NZ$207
includes taxes & fees
19 Oct - 20 Oct
La Certosa di Pontignano
A bedroom with a stone wall, a bed, a nightstand, a window, and a mirror.
A patio area with a gravel path, wooden chairs, and a table. There is a building with a stone wall and a door.
A poolside area with lounge chairs and a swimming pool.
An outdoor dining area with tables and chairs, a stone wall, and a wooden ceiling.

16. Casale La Gora

Casale La Gora
Figline e Incisa Valdarno
United States
Roberto
NZ$151
includes taxes & fees
1 Nov - 2 Nov
Casale La Gora
An indoor courtyard with stone flooring, arched columns, and tables set up for dining.
A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.
A historic building with a stone facade, arched entrance, and a wooden balcony.
An indoor swimming pool with clear glass walls, wooden beams, and large windows.

17. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Ana
NZ$251
includes taxes & fees
1 Nov - 2 Nov
Villa Casagrande Resort & SPA
A modern interior with a piano, dining area, and a large decorative animal statue.
A hotel room with a large bed, two bedside tables, a desk, a chair, and a window with curtains.
A reception desk with a modern design, a flat-screen TV, and a glass partition.
A hotel gym with stationary bikes, a treadmill, and dumbbells.

18. B&B Hotel Arezzo

B&B Hotel Arezzo
Arezzo
Italy
Marco
NZ$144
includes taxes & fees
11 Oct - 12 Oct
B&B Hotel Arezzo
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A pathway leading to a pool area with lounge chairs and umbrellas.
A stone building with a clear view of a lush green landscape, including trees and a distant mountain range.
A sunroom with wooden flooring, tables with green tablecloths, and hanging plants.

19. Le Lappe

Le Lappe
Cavriglia
Canada
William
NZ$833
includes taxes & fees
1 Nov - 2 Nov
Le Lappe
A historic stone building with multiple windows and a courtyard.
A stone building with outdoor seating and a garden with roses.
A pool area with lounge chairs and a service person attending to a guest.
A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

20. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
NZ$1,428
includes taxes & fees
25 Oct - 26 Oct
Borgo San Felice Resort
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Top San Leolino Hotel Reviews

Recent Reviews in San Leolino

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."
Elizabeth 1-night trip
Posted 15 hours ago
Fattoria di Vegi
Hotel Athena

Hotel Athena

10/10 Excellent
"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."
Michele 2-night trip
Posted 1 day ago
Hotel Athena
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"good to stay"
Jinhee 1-night trip
Posted 2 days ago
La Certosa di Pontignano
Hotel Minerva

Hotel Minerva

10/10 Excellent
"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."
Michael 1-night trip
Posted 3 days ago
Hotel Minerva
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

8/10 Good
"Staff are nice!"
GUANGMIN 2-night trip
Posted 4 days ago
Borgo Scopeto Wine & Country Relais
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent
"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."
Maya 4-night trip
Posted 4 days ago
Hu Norcenni Girasole Village
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."
Reid 2-night trip
Posted 4 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Really enjoyed our stay. Room was spacious and clean. Very nice breakfast and the staff were very kind and helpful."
Scott 2-night trip
Posted 6 days ago
Hotel Chiusarelli
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent
"Beautiful hotel that is close to a bus line to get into the city. The views and accommodations make this a wonderful place to stay."
Heather 6-night trip
Posted 6 days ago
Villa Ermellina Siena, a Tribute Portfolio Hotel

More cheap accommodation in San Leolino

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
NZ$110
1 Nov - 2 Nov
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
NZ$251
4 Oct - 5 Oct
includes taxes & fees
7.8/10 Good! (442 reviews)
Piccolo Hotel Etruria
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
NZ$283
28 Oct - 29 Oct
includes taxes & fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
NZ$295
19 Oct - 20 Oct
includes taxes & fees
8.8/10 Excellent! (108 reviews)
Albergo Centrale
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
NZ$309
20 Oct - 21 Oct
includes taxes & fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta 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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 hotel booking in San Leolino with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on San Leolino hotels. Plus, you'll earn OneKeyCash™* 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 Leolino?
Prices for hotels in San Leolino often vary, but you can find a great deal from NZ$110 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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