Pienza Vacation Packages 2025/2026 from $761

Pienza flight + hotel vacation packages

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

Grand Hotel Cavour

Historic Centre of Florence

Save 100% on your flight

per person

Sep 23 - Sep 26

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a gym and a rooftop terrace. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

per person

Sep 29 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Enjoy the free buffet breakfast each morning. A snack bar/deli and a safe deposit box are also provided.

Aurum Firenze

Historic Centre of Florence

Save 100% on your flight

per person

Sep 29 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Free WiFi in public areas and a safe deposit box are available at this hotel. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Palazzo Firenze by Baglioni Hotels & Resorts

Historic Centre of Florence

Save 100% on your flight

per person

Sep 29 - Oct 5

found 11 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the free buffet breakfast each morning.

Villa Tolomei Hotel & Resort

Oltrarno

Save 100% on your flight

per person

Sep 28 - Oct 4

found 23 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.

Top Pienza hotels deals

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26, Pienza, SI

Free Cancellation

Reserve now, pay when you stay

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This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Pool

Breakfast included

Hotel Corsignano

Via Della Madonnina 11, Pienza, SI

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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

Tenuta Santo Pietro

Localita Santo Pietro 29, Pienza, SI

$206 nightly

$232 total

Aug 11 - Aug 12

Total includes 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

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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 Il Macchione

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

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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

Agriturismo Poggio Tobruk

Loc. Spedaletto Poggio Tobruk, Pienza, SI

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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.

Popular places to visit

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

Pienza Cathedral

5/5(131 reviews)

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

Historic Centre of Pienza

Explore the great outdoors at Historic Centre of Pienza, a lovely green space in Pienza. Discover the countryside and churches in this quaint area.

Palazzo Piccolomini

5/5(80 reviews)

You can study the exhibits at Palazzo Piccolomini, a museum with a storied past, during your trip to Pienza. While you're here, you can savor the wineries.

Frequently asked questions

How much are vacation packages to Pienza?

Your travel fantasies can become a reality in Pienza for as low as $761. 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.