Book The Best Hotels in San Rocco a Pilli for 2026 from CA $105 - Fully Refundable Options

Our top choices for San Rocco a Pilli hotels

Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Sovicille

Sergey

CA $154 total

includes taxes & fees

Jul 4 - Jul 5

Agriturismo San Sano

Gaiole in Chianti

Shawn

CA $186 total

includes taxes & fees

Jun 5 - Jun 6

Seasonal outdoor pool, open 9:30 AM to 7:00 PM, pool umbrellas

SI Montalcino Hotel

Montalcino

Mark

CA $215 total

includes taxes & fees

Jun 17 - Jun 18

Hotel Ristorante La Dama nella Vigna

Monteriggioni

Norma

CA $195 total

includes taxes & fees

Jun 14 - Jun 15

Castello

Sovicille

Ivona

CA $140 total

includes taxes & fees

Jun 5 - Jun 6

Podere Brizio

Montalcino

karen

CA $358 total

includes taxes & fees

Jun 7 - Jun 8

Hotel Casafrassi Wine Resort

Castellina in Chianti

Alex

CA $104 total

includes taxes & fees

Jun 5 - Jun 6

Palace Hotel Due Ponti

Due Ponti

Jack

CA $137 total

includes taxes & fees

Jun 7 - Jun 8

La Certosa di Pontignano

Castelnuovo Berardenga

Juan

CA $211 total

includes taxes & fees

Jun 10 - Jun 11

Villa Sabolini

Colle di Val d'Elsa

DEANA

CA $266 total

includes taxes & fees

Jun 21 - Jun 22

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Capanna Suites

Montalcino

Andrew

CA $650 total

includes taxes & fees

Jun 21 - Jun 22

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

CA $124 total

includes taxes & fees

Jun 18 - Jun 19

Le Ragnaie

Montalcino

Douglas

CA $274 total

includes taxes & fees

Jun 16 - Jun 17

Relais la Costa - Dimora Storica

Monteriggioni

Roberto Javier Sanz

CA $269 total

includes taxes & fees

Jun 30 - Jul 1

Hotel Pescille by Double Hospitality

San Gimignano

Tania

CA $215 total

includes taxes & fees

Jun 11 - Jun 12

Hotel Vecchia Oliviera

Montalcino

Laura

CA $213 total

includes taxes & fees

Jun 11 - Jun 12

Albergo Giardino

Montalcino

Dean

CA $176 total

includes taxes & fees

Jun 11 - Jun 12

Villa Le Prata - Residenza del Vescovo

Montalcino

Vincenzo

CA $738 total

includes taxes & fees

Jun 9 - Jun 10

Outdoor pool, free cabanas, pool umbrellas

Borgo Santo Pietro

Chiusdino

Andrew

Fattoria di Vegi

Castellina in Chianti

CA $538 total

includes taxes & fees

Jun 11 - Jun 12

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Top San Rocco a Pilli Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"AC worked well Walking distance to town with excellent and affordable restaurants. It is an uphill walk back on the road Beautiful property"

Relais Vignale & Spa

4/10 Poor

"Honestly, I've had better stays at Motel 6. The staff were mostly indifferent about any of my requests. The room and facilities simply didn't measure up to the cost. The room was small - hardly room to open one suitcase, let alone two. No soap, or body wash dispenser in the shower. The only option was to drop the tiny hotel bar of soap on the floor, then hope you didn't kill yourself picking it up again. No Kleenex either. Yes, it's a small thing but at the price they charge... And the hotel is on a steep hillside, with stairs, stairs and more stairs. Not easy for anyone with even slight mobility issues. The one bright spot was the view from our room's terrace. The restaurant also has lovely views out over the Tuscan countryside. But overall ABSOLUTELY not worth the money."

Hotel Italia

10/10 Excellent

"Great place if you want to stay right outside the ZTL zone and the wall (beware of that if you are driving). Such a gem of hotel. The staff was super helpful, very kind and serviceable, i mean really really really nice. The room was a little tight for 4, but the bathroom was huge! All super clean, really impeccable. Our bedroom was in the adjacent building but in the ground floor, which made rolling in the luggage a breeze. The room itself had a queen bed and a day bed with a trundle. They were so nice and had the beds made for 4 when we arrived, i.e. they took out the trundle and made the bed as well as the daybed. I yet have to see that happen in the US... very attentive to detail. A very very minor thing, but the bed covers should be updated to be a bit more modern, looked like my grandma's curtains. Nevertheless, it was perfect for one night and also greatly appreciated the AC. The brick ceilings were also very charming. The breakfast buffet is absolutely amazing! Well worth the stay. They also have parking, but you need to reserve it ahead. We had gotten an email a couple of days before, but bc we were traveling around, I missed their ask if we wanted parking. Nevertheless, we found parking right behind the building so didn't matter at all, but you need to ask ahead for parking as they have limited spots A walk to the center if town is about 20mn and very easy stroll. This place is just perfect!! And Siena is just one of my favorite cities in Italy!!! Perfect combo!"

Dievole Wine Resort

8/10 Good

"While everything was wonderful it was shame that our shower water was leaking out to the bathroom floor. Had to use extra towers to soak up the water. If we were staying more than a night, I would have ask to change the room. Other than that, staffs were wonderful, the dinner was delicious and the olive oil tasting experience was fun. Would highly recommend least two nights stay here. We wanted to extend our one night stay but the weather called for rain next day."

Borgo Santo Pietro

2/10 Terrible

"While the property itself is beautiful, our overall experience was extremely disappointing and fell far below the standard we expected. From the moment we arrived, we encountered multiple issues that were handled poorly by management and staff. Our initial room had no functioning air conditioning, making it uncomfortable and unusable. We were initially told the hotel was fully booked, yet we were eventually moved to another room after considerable discussion. This was particularly frustrating given that we had even offered to pay for an upgraded room. The most disappointing aspect of our stay was the way my wife was treated. When she respectfully raised concerns regarding several issues we experienced, members of the staff responded dismissively and, at times, appeared to laugh at her concerns rather than address them professionally. No guest should ever be made to feel ignored or ridiculed when raising legitimate issues. To make matters worse, hotel staff damaged my wife’s luggage during our stay. Management acknowledged the issue and repeatedly assured us that they would resolve it and make things right. However, after we checked out, those assurances turned into delays, excuses, and ultimately a complete lack of communication. Despite multiple commitments to address the matter, management stopped responding altogether. We booked this property expecting a memorable and exceptional experience for a special occasion. Unfortunately, it was terrible and staff underwhelming."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Super emplacement! Très beau et charmant!! Bien situé, facilement accessible en voiture et près des stationnements du village de San Gimignano! Le personnel de l'hôtel nous ont fait de bonnes recommandations et nous ont même donné en temps réel le nombre de places de stationnement au village!! Confortable et chaleureux! Le restaurant de l'hôtel est excellent aussi! Belle piscine et environnement incroyable pour le déjeuner également! Bref, nous avons eu un bon moment de détente. Nous recommandons fortement!!"

More cheap stays in San Rocco a Pilli

Cannon d'Oro

Via Montanini 28 Siena SI

CA $132

CA $153 total

Jul 4 - Jul 5

includes taxes & fees

7.8/10 Good! (258 reviews)

Hotels in San Rocco a Pilli with star rating

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 $105 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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Our top choices for San Rocco a Pilli hotels

Tuscasì Aparthotel

Agriturismo San Sano

SI Montalcino Hotel

Hotel Ristorante La Dama nella Vigna

Castello

Podere Brizio

Hotel Casafrassi Wine Resort

Palace Hotel Due Ponti

La Certosa di Pontignano

Villa Sabolini

Capanna Suites

Mercure Petriolo Siena Terme Spa Hotel

Le Ragnaie

Relais la Costa - Dimora Storica

Hotel Pescille by Double Hospitality

Hotel Vecchia Oliviera

Albergo Giardino

Villa Le Prata - Residenza del Vescovo

Borgo Santo Pietro

Fattoria di Vegi

Top San Rocco a Pilli Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

More cheap stays in San Rocco a Pilli

Cannon d'Oro

Hotels in San Rocco a Pilli with star rating

Frequently asked questions

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