Name: Hotel San Gregorio
Price range: $177 total
Rating: 9.4

The Latest Val d'Orcia vacation packages

Price found within the past 48 hours. Click for updated prices.

Aurum Uffizi

Historic Centre of Florence

$1,553

per person

May 20 - May 24

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,002 reviews)

Great location, but on a noisy alley.

Reviewed on Mar 20, 2026

Hotel Alessandra

Historic Centre of Florence

$4,817

per person

Jun 9 - Jun 15

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Florence (FLR)

9.2/10 Wonderful! (853 reviews)

Staying here was a wonderful experience! Hotel Alessandra was within walking distance of everything we wanted to see in Florence, including one street away from the Ponte Vecchio. The room was always very clean and the staff was extremely welcoming and kind. We loved our stay here and would absolutely stay here on our next trip to Florence!

Reviewed on Mar 30, 2026

Hotel Berchielli

Historic Centre of Florence

$5,448

per person

Jun 9 - Jun 15

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Florence (FLR)

9.4/10 Exceptional! (1,001 reviews)

Very good Breakfast with many food options. Great service !

Reviewed on Jan 21, 2026

Hotel De La Ville

Historic Centre of Florence

$5,411

per person

Jun 2 - Jun 8

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Florence (FLR)

9.2/10 Wonderful! (1,003 reviews)

Everything about the room was fine but the AC didn’t work. Other than that it was fine.

Reviewed on Mar 28, 2026

The FRAME Hotel

Historic Centre of Florence

$5,593

per person

Jun 2 - Jun 8

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Florence (FLR)

9.6/10 Exceptional! (623 reviews)

Staff was so nice! Room was clean and well maintained. Location is great would definitely come back

Reviewed on Mar 18, 2026

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Discover the most popular places to visit in Val d'Orcia

Pienza Cathedral

Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.

Castello Banfi

You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas, or simply enjoy its wineries.

Baths of San Filippo

You can take time to visit Baths of San Filippo during your travels to Bagni San Filippo. Visit the area's spas, or simply enjoy its wineries.

What to do in Val d'Orcia

Montalcino: Guided Winery Tour and Wine Tasting

$52

per adult

Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

$81

per adult

Seggiano: Guided Tour of the Olive Grove and Food Tasting

$29

per adult

See all activities in Val d'Orcia

Val d'Orcia Hotel Deals

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26 Pienza SI

Fully refundableReserve now, pay when you stay

$94 nightly

$110 total

Apr 8 - Apr 9

Total with taxes and fees

8.8/10 Excellent! (635 reviews)

A little tired, extremely clean, with an amazing staff

Reviewed on Jan 1, 2026

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

Fully refundableReserve now, pay when you stay

$1,494 nightly

$1,655 total

Apr 16 - Apr 17

Total with taxes and fees

10/10 Exceptional! (74 reviews)

Everything was perfect

Reviewed on Mar 25, 2026

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI

$155 nightly

$177 total

Apr 2 - Apr 3

Total with taxes and fees

9.4/10 Exceptional! (139 reviews)

A wonderful hotel - great location, friendly staff, comfortable rooms.

Reviewed on Mar 25, 2026

See all 630 properties in Val d'Orcia

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.