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Our top choices for San Rocco a Pilli hotels

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $96
CA $126 total
includes taxes & fees
May 22 - May 23
Tuscasì Aparthotel

SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (384 reviews)
"The staff were friendly and very helpful & accommodating. The beds were comfortable and the breakfast was abundant and good options. A great place to stay."
United States
Mark
The price is CA $183
CA $214 total
includes taxes & fees
Jun 17 - Jun 18
SI Montalcino Hotel

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (529 reviews)
"Friendly staff, beautiful property, delicious included breakfast, great dinner, and all around good experience. Only think I'd like to see is a gym, but luckily there's tons of hills to run to get a great workout 😄"
United States
Alex
The price is CA $206
CA $233 total
includes taxes & fees
Jun 7 - Jun 8
La Certosa di Pontignano

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (87 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 CA $134
CA $154 total
includes taxes & fees
May 18 - May 19
Agriturismo San Sano

Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (157 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 CA $306
CA $349 total
includes taxes & fees
Jun 7 - Jun 8
Podere Brizio

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (39 reviews)
"Great place to stay and visit all the surrounding hill towns! Breakfast was excellent. Daniela took amazing care of us! Will definitely return!"
United States
Norma
The price is CA $167
CA $191 total
includes taxes & fees
Jun 14 - Jun 15
Hotel Ristorante La Dama nella Vigna

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is CA $392
CA $441 total
includes taxes & fees
May 28 - May 29
2 Cuori e 1 Yurta Glamping in Toscana

Agriturismo SOLE

Agriturismo SOLE
Trequanda
The price is CA $469
CA $521 total
includes taxes & fees
Jun 9 - Jun 10
Agriturismo SOLE

Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (326 reviews)
"Great place to stay the staff was super friendly and very close to Monalcino. Good wine everywhere. The scenery was so beautiful! "
United States
Douglas
The price is CA $234
CA $273 total
includes taxes & fees
Jun 11 - Jun 12
Le Ragnaie

Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
3.0 star property
Montalcino
9.6 out of 10, Exceptional, (64 reviews)
"Perfect location and wonderful staff!"
United States
Laura
The price is CA $195
CA $221 total
includes taxes & fees
Jun 2 - Jun 3
Hotel Vecchia Oliviera

Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (83 reviews)
"Great location. Great wine. Great staff. "
United States
Vincenzo
The price is CA $652
CA $733 total
includes taxes & fees
Jun 7 - Jun 8
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, (203 reviews)
"What a lovely stay at a beautiful historic hotel. The grounds are so well kept and peaceful. Dinner was amazing both nights, highly recommend this property. "
Canada
DEANA
The price is CA $242
CA $273 total
includes taxes & fees
May 20 - May 21
Villa Sabolini

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (136 reviews)
"Excellent hotel, very beautiful, peaceful and serene. Rooms are gorgeous and spacious. Food and service is incredible. Felt very high end and relaxing the whole time! "
United States
Andrew
The price is CA $637
CA $716 total
includes taxes & fees
Jun 8 - Jun 9
Capanna Suites

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very good, (57 reviews)
"Exceptional service, good breakfast "
United States
borjan
The price is CA $112
CA $131 total
includes taxes & fees
Jun 11 - Jun 12
Palace Hotel Due Ponti

Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (185 reviews)
"Beautiful property and very friendly helpful staff"
Canada
Pamela
The price is CA $388
CA $440 total
includes taxes & fees
Jun 3 - Jun 4
Dievole Wine Resort

One Belvedere Tuscany

One Belvedere Tuscany
Poggibonsi
The price is CA $765
CA $848 total
includes taxes & fees
May 18 - May 19
One Belvedere Tuscany

Hotel Dei Capitani

Hotel Dei Capitani
3.0 star property
Montalcino
8.8 out of 10, Excellent, (434 reviews)
"Air conditioner didn’t work during our entire stay."
United States
Kimberly
The price is CA $220
CA $254 total
includes taxes & fees
Jun 4 - Jun 5
Hotel Dei Capitani

Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
9.0 out of 10, Wonderful, (40 reviews)
"Super stay !! "
Canada
Patryk
The price is CA $195
CA $221 total
includes taxes & fees
May 25 - May 26
Fattoria Pieve a Salti

Castello

Castello
3.0 star property
Sovicille
8.6 out of 10, Excellent, (73 reviews)
"Great little place to stay overnight. "
United States
Ivona
The price is CA $120
CA $139 total
includes taxes & fees
May 24 - May 25
Castello

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (126 reviews)
"Perfectb Quiet and very relaxing stay. Breakfast was very tasty and the view was absolutely spectacular "
United Kingdom
Mayara
The price is CA $189
CA $217 total
includes taxes & fees
Jun 11 - Jun 12
Castello di Leonina Relais
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, 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 Rocco a Pilli.
How can I save on a San Rocco a Pilli hotel booking with Expedia?
Members always get our best prices. Find our best San Rocco a Pilli hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a San Rocco a Pilli hotel?
Prices for hotels in San Rocco a Pilli often vary, but you can find a great deal from CA $103 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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