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Our top choices for San Rocco a Pilli hotels

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$171
includes taxes & fees
10 July - 11 July
Tuscasì Aparthotel

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (143 reviews)
"We thoroughly enjoyed our stay at Capanna Suites - the property and room was very well thought out and beautiful, the sunset view was amazing and the staff were extremely helpful (thanks in particular to Giulia). We felt well recharged after our stay, especially after the spa session."
Singapore
Jonathan
The price is NZ$603
includes taxes & fees
31 July - 1 Aug
Capanna Suites

Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (161 reviews)
"Beautiful hotel, near to Montalcino and a lot winerys, very calm and charm the property Good breakfast Staff very kindly and attentive I recommend!!!!"
Mexico
Orlando Santini
The price is NZ$445
includes taxes & fees
22 July - 23 July
Podere Brizio

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (546 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 NZ$290
includes taxes & fees
3 Aug - 4 Aug
La Certosa di Pontignano

SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (395 reviews)
"The hotel was absolutely stunning! Our room was spacious, and the beds were incredibly comfortable. The staff were warm, welcoming, and very informative throughout our stay. Breakfast was delicious, and there was no better way to start the day than with an espresso while enjoying the beautiful view. We had a wonderful experience and would definitely stay here again."
Canada
Jacqueline
The price is NZ$240
includes taxes & fees
9 July - 10 July
SI Montalcino Hotel

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (97 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 NZ$193
includes taxes & fees
8 July - 9 July
Agriturismo San Sano

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (45 reviews)
"One of our favorite stays in Italy! Few number of rooms which makes it feel very relaxing and comfortable. Staff was friendly and helpful."
Canada
Yael
The price is NZ$236
includes taxes & fees
15 July - 16 July
Hotel Ristorante La Dama nella Vigna

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
The price is NZ$476
includes taxes & fees
9 July - 10 July
Castello di Tornano Wine Resort

Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (86 reviews)
"Great location. Great wine. Great staff. "
United States
Vincenzo
The price is NZ$1,031
includes taxes & fees
20 July - 21 July
Villa Le Prata - Residenza del Vescovo

Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (216 reviews)
"Great Toscana hotel"
United States
Jose
The price is NZ$350
includes taxes & fees
9 July - 10 July
Villa Sabolini

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 NZ$169
includes taxes & fees
10 July - 11 July
Palace Hotel Due Ponti

Borgo San Felice Resort

Borgo San Felice Resort
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (85 reviews)
"Absolutely wonderful!"
Canada
Cynthia
The price is NZ$1,257
includes taxes & fees
5 Aug - 6 Aug
Borgo San Felice Resort

Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (328 reviews)
"I would not change a thing. It was amazing great hospitality nice clean. I would definitely go back. Highly recommended."
United States
Jeton
The price is NZ$264
includes taxes & fees
15 July - 16 July
Le Ragnaie

Castello

Castello
3.0 star property
Sovicille
8.6 out of 10, Excellent, (75 reviews)
"This hotel was fantastic! A gem, off the beaten path. Plenty of space and quiet accompanied by crisp fresh air. The restaurant in the hotel lobby was delicious and affordable. I hope to return here."
United States
Martin
The price is NZ$159
includes taxes & fees
19 July - 20 July
Castello

Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (186 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 NZ$280
includes taxes & fees
10 July - 11 July
Belvedere di San Leonino

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
9.8 out of 10, Exceptional, (8 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 NZ$658
includes taxes & fees
7 Aug - 8 Aug
Fattoria di Vegi

Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
3.0 star property
Montalcino
9.4 out of 10, Exceptional, (69 reviews)
"Perfect location and wonderful staff!"
United States
Laura
The price is NZ$287
includes taxes & fees
8 July - 9 July
Hotel Vecchia Oliviera

Castello La Leccia

Castello La Leccia
Castellina in Chianti
10.0 out of 10, Exceptional, (112 reviews)
"Amazing property with great staff."
United States
Samuel
The price is NZ$530
includes taxes & fees
15 July - 16 July
Castello La Leccia

Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (198 reviews)
"Beautiful property and very friendly helpful staff"
Canada
Pamela
The price is NZ$660
includes taxes & fees
27 July - 28 July
Dievole Wine Resort

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 NZ$395
includes taxes & fees
31 July - 1 Aug
Relais la Costa - Dimora Storica
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 Rocco A Pilli?
The best area to stay in San Rocco A Pilli is within the village itself, or in one of the charming agriturismos or villas located in the surrounding Tuscan countryside.

Staying directly in San Rocco A Pilli village provides convenience. You'll find local shops, a few restaurants, and essential services within easy walking distance. It's a small, friendly community, offering a glimpse into daily Tuscan life.

Couples looking for a romantic and tranquil escape will find the agriturismos and villas just outside the village particularly appealing. These properties often feature stunning views of the rolling hills, olive groves, and vineyards. They typically offer a more secluded experience, often with a swimming pool and opportunities for wine tasting or cooking classes on-site. It's an excellent option for those who appreciate privacy and the picturesque Tuscan landscape.
When is the best time to go to San Rocco A Pilli?
The best time to go to San Rocco A Pilli for pleasant weather and fewer crowds is during the shoulder seasons of late April to May and September to early October.

During these months, the Tuscan countryside is particularly beautiful, with wildflowers blooming in spring and vineyards heavy with grapes in autumn. The temperatures are comfortably warm, typically ranging from 20-25°C, making it ideal for exploring the rolling hills, olive groves, and nearby historic towns without the intense heat of summer. You'll find it easier to secure reservations at popular local restaurants and attractions, as well as more favourable rates for villas and agriturismi. This period is superb for couples seeking a relaxed, romantic getaway or solo travellers looking for a peaceful escape to enjoy the region's natural beauty and culinary delights.

For those who enjoy warmer weather and don't mind more fellow travellers, June and July offer long, sunny days with temperatures often exceeding 30°C. This is the peak season, so while the weather is glorious for poolside relaxation and outdoor dining, you'll encounter more visitors and higher prices. Families often find this time suitable due to school holidays, and the longer daylight hours allow for extended day trips to Siena, Florence, or the Chianti region.
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 Rocco a Pilli.
How can I save on a hotel booking in San Rocco a Pilli with Expedia?
One Key™ – Expedia's free travel rewards programme – gives you instant access to perks and Member Prices on San Rocco a Pilli 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 Rocco a Pilli?
Prices for hotels in San Rocco a Pilli often vary, but you can find a great deal from NZ$141 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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