Name: Hotel San Gregorio
Price range: $172 total
Rating: 9.2

Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Val d'Orcia vacation packages

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

Eurostars Florence Boutique

Historic Centre of Florence

Save 100% on your flight

$1,259

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Florence (FLR)

8.6/10 Excellent! (476 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Aurum Firenze

Historic Centre of Florence

Save 100% on your flight

$1,877

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,002 reviews)

9 day stay. The property hit my must-haves! Central location, clean, affordable, and safe. 5/5 in all these areas! There is nothing they can do about dirty streets but the filth did not cross the threshold. T2 tram from the airport is 2 blocks away. The central market is 2 blocks in the other direction. Key card swipe after dark. 24 hour desk service. Breakfast on the 5th floor with views. Very courteous staff. The only complaint is breakfast tables are cleared very quickly while I went for a americano refill. Will definitely return here.

Reviewed on Jan 3, 2026

The Moon Boutique Hotel & Spa

Historic Centre of Florence

Save 100% on your flight

$1,446

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Florence (FLR)

9.6/10 Exceptional! (495 reviews)

The spa was wonderful though the jacuzzi could be hotter I think! The only complaint was that the bed wasn’t very comfortable (it was pretty hard) and the pillows were rather flat.

Reviewed on Jan 2, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

Save 100% on your flight

$2,682

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

8.8/10 Excellent! (939 reviews)

Very quiet, huge room. Very comfortable bed. In a perfect location, staff is very friendly.

Reviewed on Jan 13, 2026

Rivoli Boutique Hotel

Historic Centre of Florence

Save 100% on your flight

$1,544

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Florence (FLR)

9/10 Wonderful! (1,000 reviews)

Fourth time staying here. Love this hotel - staff, rooms, location and breakfast

Reviewed on Oct 29, 2025

Don't see what you're looking for?

See all available trips from Columbus to Val d'Orcia

View all trips

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

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

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

Get rates

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

Get rates

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI

$150 nightly

$172 total

Feb 22 - Feb 23

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 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.