Pienza Vacation Packages 2026 from $1,419

Pienza flight + hotel vacation packages

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

Villa Tolomei Hotel & Resort

Oltrarno

$1,419

per person

Jan 10 - Jan 15

found 24 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Hotel Berchielli

Historic Centre of Florence

$1,909

per person

Jan 10 - Jan 15

found 24 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center, laundry service, and airport shuttle. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Hotel Roma

Historic Centre of Florence

$1,786

per person

Jan 10 - Jan 15

found 24 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

This hotel features a gym and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and limo/town car service are also offered.

Grand Hotel Cavour

Historic Centre of Florence

$1,441

per person

Jan 10 - Jan 15

found 24 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

This hotel features a gym and a rooftop terrace. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Donati Luxury Tower Suites

Historic Centre of Florence

$1,858

per person

Jan 10 - Jan 15

found 24 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

This hotel features free WiFi in public areas, concierge services, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

Top Pienza hotels deals

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$149 total

Nov 8 - Nov 9

Total with taxes and fees

This residence features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. You'll appreciate the area shuttle, self parking, and coffee shop/cafe.

Pool

Pet friendly

Hotel Corsignano

Via Della Madonnina 11 Pienza SI

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$135 total

Nov 11 - Nov 12

Total with taxes and fees

This smoke-free hotel features 2 hot tubs, a restaurant, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and airport shuttle. You'll appreciate the area shuttle, free parking, and terrace.

Hot Tub

Pet friendly

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI

$147 nightly

$167 total

Nov 10 - Nov 11

Total with taxes and fees

An attached winery and an outdoor pool are featured at this hotel. Families will appreciate the playground, onsite laundry facilities, and babysitting. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.

Pool

Breakfast included

Tenuta Santo Pietro

Localita Santo Pietro 29 Pienza SI

$229 nightly

$256 total

Oct 20 - Oct 21

Total with taxes and fees

An attached winery and a restaurant are featured at this smoke-free farm stay. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking. A bar/lounge, a poolside bar, and a terrace are also provided.

Pool

Breakfast included

Podere Spedalone

Strada per Cosona SP71 Pienza SI

$154 nightly

$174 total

Oct 30 - Oct 31

Total with taxes and fees

A restaurant and a seasonal outdoor pool are featured at this farm stay. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Pool

Breakfast included

Agriturismo Poggio Tobruk

Loc. Spedaletto Poggio Tobruk Pienza SI

$159 nightly

$179 total

Oct 18 - Oct 19

Total with taxes and fees

This farm stay doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Parking included

Free WiFi

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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.

Stay near popular Pienza attractions

A historic church with a bell tower, arched windows, and a central dome.

Pienza Cathedral

9.4/10 (460 reviews)

You can learn about the history of Pienza with a trip to Pienza Cathedral. While you're here, you can savor the wineries.

See properties

Frequently asked questions

How much are vacation packages to Pienza?

Your travel fantasies can become a reality in Pienza for as low as $1,419. Vacation packages include flights and hotels, so organizing everything should be easy as pie. The only thing you'll need to worry about is what amazing attraction you'll head to first.

How long should my Pienza vacation be?

If you're looking for some guidance, most visitors spend about 3 nights in Pienza. But to uncover the true essence of this place, stay a few extra days. That way you can check off more attractions and really experience the local culture.

Where can I get the best vacation package deals for Pienza?

Walking away with the perfect package deal to Pienza couldn't be easier with Travelocity. With as many as 400 air carriers and 1,000,000 properties across the globe, you're spoiled for choice when it comes to your flights and hotels.

Why should I book my Pienza vacation package with Travelocity?

Because you'll never wander on your own if you lock in your vacation through us, and we offer round-the-clock support and high-quality service to boot. Add to that our Price Match Guarantee and tons of destinations to select from. We're here to help you have the trip of a lifetime.

Will I save money on my Pienza car rental if I book it with my hotel or flight?

Bundling your car, hotel and flight into a Pienza vacation package is an excellent way to score better prices. Plus, having your own car rental gives you total freedom to get to all those big-name sights you'd like to see. Located 90 mi from Pienza, St. Peters Basilica is one attraction that should be on your must-do list. Turn up the tunes and make a day trip of it.

What is the best time of year to go to Pienza?

February, May and July is peak season here, while March, November and December usually experience less crowds. If your bank balance is your main consideration, try to avoid traveling in as it tends to be the dearest time. The least expensive month to see this part of the world is .

Which airport is best for Pienza?

Peretola Airport (FLR) is 55 mi northwest of the heart of Pienza.

What is there to do in Pienza?

There is a certain magic in the air as you stroll through the streets of Pienza. Pienza Cathedral and Palazzo Piccolomini are just a couple of landmarks that make this city so special, so add them to your list of places to see.

Where should I stay when visiting Pienza?

Many travelers stay at the Relais Val Dorcia. It's a great base for your Pienza escape.