Pienza Vacation Packages

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Your Pienza Vacation

Get ready to experience Pienza in your own style with a custom Pienza vacation package! Uncovering the charms of this captivating city is made simpler with a base in a neighborhood such as Macciano, which is great for walking, among other things. If sightseeing is on the to-do list during your trip to Pienza, visit big attractions like Pienza Cathedral, Palazzo Piccolomini and Chapel of our Lady of Vitaleta. Check out Expedia's wide range of travel options and start organizing your ultimate vacation to Pienza now.

Top Pienza Vacation Deals

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
Oct 5 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
The hotel is situated on busy street, it is walking distance from Santa Maria train station, the room was clean but small and the breakfast was average.

Reviewed on Jul. 25, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
Oct 5 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun. 6, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
per person
Oct 5 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
No reviews
Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul. 18, 2025

Collegio alla Querce - Auberge Resorts

Collegio alla Querce - Auberge Resorts

5 out of 5
Le Cure
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (1 review)

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Pienza Hotel Deals

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Jul 27 to Jul 28
CA $89
CA $107 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (572 reviews)
"We had a fantastic time . The most perfect location for a hotlet, right in the tow with stunning views . Would definitely recommend."

Reviewed on Jul. 25, 2025

Hotel Relais II Chiostro di Pienza
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11, Pienza, SI
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Aug 3 to Aug 4
CA $246
CA $280 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (301 reviews)
"All 1st class. Food excellent"

Reviewed on Jul. 20, 2025

Hotel Corsignano
Tenuta Santo Pietro

Tenuta Santo Pietro

Localita Santo Pietro 29, Pienza, SI
The price is CA $271 per night from Aug 25 to Aug 26
CA $271
CA $305 total
Aug 25 - Aug 26
includes taxes & fees
9.6/10 Exceptional! (111 reviews)
Family trip
"Beautiful place to be with family!"

Reviewed on Jul. 2, 2025

Tenuta Santo Pietro
See all 6,194 properties in Pienza
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.
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Discover the most popular places to visit in Pienza

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

Pienza Cathedral

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

Pienza Cathedral

Art Studio di Adelina Quadri

You can spend an afternoon browsing the exhibits at Art Studio di Adelina Quadri during your travels in Monticchiello. While you're here, you can savor the wineries.

Art Studio di Adelina Quadri

What to do in Pienza

Val D'Orcia Dreaming!!

Val D'Orcia Dreaming!!

CA $315
per adult
Val D'Orcia Dreaming!!
Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

CA $288
per adult
Pienza & Montepulciano Small Group Tour from Siena
Pienza: Private Walking Tour with Tuscan Tasting Experience

Pienza: Private Walking Tour with Tuscan Tasting Experience

CA $554
per traveller
Pienza: Private Walking Tour with Tuscan Tasting Experience
See all activities in Pienza

Frequently asked questions

How much does a Pienza vacation package cost?
You'll find cheap prices from CA $1,641 on Expedia for your Pienza escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Pienza costs.
What are the cheapest months to go to Pienza?
December, January and February are great times to look for cheap Pienza vacation packages. Choosing to travel in quieter months means you can usually find lower prices on flights and hotels.
How many days is enough for Pienza?
The ideal length for your Pienza vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to tick off all the main sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Pienza?
Well known for its walking trails, hiking and festivals, a Pienza vacation is a hit with all types of travellers. Be sure to check out top sights like Palazzo Piccolomini and Historic Centre of Pienza, and consider renting some wheels for day trips to explore even more.
How to find the best Pienza package deals?
Use Expedia's filters to help you find some unbeatable Pienza package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Pienza package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Pienza vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels separately. Better still, you can personalize your Pienza trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Pienza?
Score incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Pienza escape.
How to plan a trip to Pienza?

  1. Pick your travel dates: What you'd like to do in Pienza and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and activities. Your accommodations will probably be the biggest expense during your trip to Pienza.
  3. Decide how long to go for: Now that you're more familiar with Pienza, you can work out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Pienza vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.