A historic square with a prominent tower and statues.

Luxury Hotels & Resorts in Pienza from AU$166

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Our top choices for Pienza luxury hotels

1. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
9.6 out of 10, Exceptional, (85 reviews)
"The natural surroundings and views around the agriturismo were beautiful, making our stay truly enjoyable. The tours and dinner options provided are excellent as well — I highly recommend taking part in them."
Japan
RYO
The price is AU$209
includes taxes & fees
19 Nov - 20 Nov
Agriturismo Il Macchione

2. La Bandita Townhouse

La Bandita Townhouse
Pienza
9.6 out of 10, Exceptional, (17 reviews)
"Great Stay!"
United States
Kristian
The price is AU$721
includes taxes & fees
10 Nov - 11 Nov
La Bandita Townhouse

3. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (170 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is AU$226
includes taxes & fees
29 Nov - 30 Nov
Hotel San Gregorio

4. Hotel Corsignano

Hotel Corsignano
4.0 star property
Pienza
9.4 out of 10, Exceptional, (397 reviews)
"Love this hotel. Very nice place in a great location and very friendly staff."
Canada
Tatiana
The price is AU$233
includes taxes & fees
15 Nov - 16 Nov
Hotel Corsignano

5. Relais Cloister Pienza

Relais Cloister Pienza
4.0 star property
Pienza
9.0 out of 10, Wonderful, (16 reviews)
"The room and view were wonderful, the breakfast was delicious, and the staff members were incredibly helpful!"
United States
Tracy
The price is AU$212
includes taxes & fees
11 Nov - 12 Nov
Relais Cloister Pienza

6. Rossellino

Rossellino
Pienza
8.6 out of 10, Excellent, (70 reviews)
"Very nice people. Glad we stayed there. Would absolutely stay there again!"
United States
Darrell
The price is AU$198
includes taxes & fees
10 Nov - 11 Nov
Rossellino

7. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is AU$199
includes taxes & fees
2 Dec - 3 Dec
Affitacamere Maria Gabriella

8. Podere Spedalone

Podere Spedalone
1.0 star property
Pienza
9.0 out of 10, Wonderful, (53 reviews)
"The common areas could be cleaner."
Ireland
Sana
The price is AU$249
includes taxes & fees
9 Nov - 10 Nov
Podere Spedalone
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.

Top Pienza Hotel Reviews

Frequently asked questions

What are the top-rated luxury hotels in Pienza?
Among the top-rated luxury hotels in Pienza, Hotel Corsignano and Hotel Relais II Chiostro di Pienza are consistently celebrated for their exceptional quality.

The Hotel Corsignano, with a 9.4 rating, offers private winery tours and features designer toiletries and premium bedding. Customers frequently praise the friendly and amazing front desk staff.

The Hotel Relais II Chiostro di Pienza, rated 8.8, provides complimentary continental breakfast and boasts a convenient location. Reviewers often highlight the clean and quiet rooms.
Which area of Pienza is best to stay in for luxury hotels?
The best area to stay in Pienza for luxury hotels is within the historic centre itself, or just outside its walls for properties offering expansive views of the Val d'Orcia.

The historic centre of Pienza is compact and pedestrian-friendly, a UNESCO World Heritage site known for its Renaissance architecture. The main street, Corso Rossellino, runs through the heart of the town, connecting the Duomo and Palazzo Piccolomini at one end to the city gates at the other. Within these ancient walls, you'll find beautifully restored buildings, many of which now house boutique hotels and guesthouses.

Couples often find staying within the historic centre to be an ideal choice. It's wonderfully romantic, with narrow streets great for evening strolls and easy access to excellent restaurants and wine bars. You're never far from a stunning viewpoint overlooking the rolling Tuscan hills, and the convenience of stepping out directly into this historic setting is a real plus.

Alternatively, for those seeking more space and panoramic vistas, several luxury hotels are situated just a short walk or drive from the town's perimeter. These properties often boast larger grounds, swimming pools, and extensive gardens, all while offering breathtaking views of the iconic Tuscan landscape. This option is particularly appealing for couples who appreciate privacy and a tranquil setting, along with the convenience of Pienza's amenities nearby.
Which luxury hotels in Pienza are good for families?
In Pienza, Hotel Corsignano and Hotel Relais II Chiostro di Pienza are well-suited for families seeking luxury hotels.

The Hotel Corsignano, with a 9.4 rating, offers great experiences such as private winery tours, which can be an engaging activity for families. Guests consistently praise the staff for being super nice, and the breakfast as great, indicating a pleasant and accommodating environment.

The Hotel Relais II Chiostro di Pienza, rated 8.8, provides complimentary continental breakfast, which is convenient for families. Its location is frequently described as convenient and amazing, making it an excellent base for exploring Pienza.
What are the best luxury hotels in Pienza with a pool?
For luxury accommodation in Pienza with a pool, Hotel Relais Il Chiostro di Pienza is an excellent choice.

The Hotel Relais Il Chiostro di Pienza, with an 8.8 rating, offers a seasonal outdoor pool with sun loungers. Customers consistently praise its convenient and amazing location, as well as its clean and quiet rooms. Complimentary continental breakfast is also provided.
Which luxury hotels in Pienza are good for couples?
For couples seeking luxury accommodation in Pienza, Hotel Corsignano is an excellent choice.

The Hotel Corsignano, with a 9.4 rating, offers a refined experience with amenities such as private winery tours and champagne service, ideal for a romantic escape. Customers frequently praise the friendly and amazing front desk staff, as well as the good location.
Are there any top luxury hotels near Piazza Pio II?
For those seeking premium accommodation near Piazza Pio II, Hotel Corsignano and Hotel Relais Il Chiostro di Pienza are two distinguished options.

The Hotel Corsignano, with a 9.4 rating, offers a refined experience with amenities such as private winery tours, designer toiletries, and champagne service. Customers frequently praise its breakfast and the exceptionally friendly front desk staff.

The Hotel Relais Il Chiostro di Pienza, rated 8.8, provides a convenient location and features complimentary continental breakfast and a swimming pool with sun loungers. Guests often highlight the cleanliness and quietude of its rooms.
What luxury activities and experiences are there in Pienza?
The best area to stay in Pienza for luxury activities and experiences is within the historic centre, or just outside its walls, offering stunning views of the Val d'Orcia.

The historic centre of Pienza is a UNESCO World Heritage site, renowned for its Renaissance architecture and its position atop a hill. The main street, Corso Rossellino, is lined with shops selling local specialities, particularly Pecorino cheese. It's a compact and walkable town, making it easy to explore its beautiful squares and enjoy its elevated position.

Couples looking for a refined experience will find staying within Pienza's walls or in a nearby villa ideal. You can enjoy private guided tours of the town's architectural highlights, such as the Duomo and Palazzo Piccolomini, followed by exclusive Pecorino cheese tastings paired with local wines. Many fine dining restaurants in the historic centre offer tasting menus featuring regional ingredients, often with tables boasting panoramic views of the Tuscan landscape.

For those seeking a more expansive luxury experience, consider a stay at a boutique hotel or a restored farmhouse just outside Pienza. These properties often feature private pools, high-end spa facilities, and offer activities like hot air balloon rides over the Val d'Orcia or private cooking classes focusing on Tuscan cuisine.
Can I cancel my luxury hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right luxury hotel in Pienza for you.
How can I save on a luxury hotel in Pienza with Expedia?
There are plenty of ways to save on a luxury hotel in Pienza. Join One Key™, our free travel rewards program, to unlock Member Prices across a range of hotels. Typically, booking in advance will help you save on hotel bookings. If you're feeling spontaneous, be sure to check for last-minute deals.
How much does a luxury hotel in Pienza cost?
Luxury hotel prices in Pienza vary, but you can find a great deal from AU$166 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates.
Is it cheaper to book a luxury Pienza hotel and flights as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.

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