Name: Hotel San Gregorio
Price range: $170 total
Rating: 9.2

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The Latest Val d'Orcia vacation packages

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

Hotel Repubblica Marinara

$617

per person

Apr 20 - Apr 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Pisa (PSA)

8/10 Very Good! (692 reviews)

Clean room. Helpful and polite staff. Ample breakfast. Excellent one night stopover after flight.

Reviewed on Sep 8, 2025

Allegroitalia San Gallo Firenze

San Lorenzo

$990

per person

Apr 16 - Apr 21

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

8.8/10 Excellent! (1,000 reviews)

Wonderful, well-presented hotel in a great location with an excellent and generous breakfast. Immaculate, spacious rooms, great proximity to city centre and tram stop just outside.

Reviewed on Dec 16, 2025

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence

Save 100% on your flight

$1,418

per person

Apr 16 - Apr 21

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

9.4/10 Exceptional! (120 reviews)

Phenomenal location!

Reviewed on Oct 18, 2025

Aurum Uffizi

Historic Centre of Florence

$919

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,000 reviews)

This is not a typical hotel where there is a lobby or staff to greet you . Instead it is a set of apartments in a corner building . The person who let us in was awaiting for us at the door at check in. Breakfast was serve in a buffet style . Staff would ask if you would order something else if you like. Continental breakfast is available .Overall it was comfortable and easy to find . Shops and restaurants are all walking distance.

Reviewed on Jan 15, 2026

Residenza Florentia

Historic Centre of Florence

$965

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

8.4/10 Very Good! (46 reviews)

Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.

Reviewed on Jun 12, 2025

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

Cathedral of Pienza featuring heritage elements, a church or cathedral and religious elements

Pienza Cathedral

5/5(131 reviews)

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

Castello Banfi

4/5(6 reviews)

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

5/5(4 reviews)

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

Seggiano: Guided Tour of the Olive Grove and Food Tasting

$29

per adult

Winery tour & wine tasting in Montalcino

$47

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

8.6/10 Excellent! (616 reviews)

A little tired, extremely clean, with an amazing staff

Reviewed on Jan 1, 2026

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Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

8.8/10 Excellent! (339 reviews)

The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing.

Reviewed on Nov 11, 2025

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Hotel San Gregorio

Via Della Madonnina 4 Pienza SI

Fully refundableReserve now, pay when you stay

$148 nightly

$170 total

Mar 4 - Mar 5

Total with taxes and fees

9.2/10 Wonderful! (134 reviews)

Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!

Reviewed on Oct 25, 2025

See all 631 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.