Pienza Vacations from $653

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Pienza vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

4 out of 5
Price was $937, price is now $653 per person
$653
per person
Jan 14 - Jan 20
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
18.4/10 Exceptional! (175 reviews)
The property is beautifully old but be careful how much luggage you bring as there is no elevator, Only stairs. Room is nice. Bathrooms nicely updated. No complaints!

Reviewed on Sep 30, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $3,265, price is now $2,209 per person
$2,209
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Florence (FLR)
19.6/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 2025

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

4 out of 5
Price was $1,222, price is now $860 per person
$860
per person
Jan 14 - Jan 20
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
19.2/10 Exceptional! (31 reviews)
Overall a lovely stay. The staff is very welcoming and accommodating. Rooms are very clean. Pool too cold to swim in even though they said that it was heated. Wirlpool/hot-tub was on the cool side too. Couldn’t get sauna to work properly -however, I should have asked. Restaurant food was very good.

Reviewed on May 12, 2025

Hotel Number Nine

Hotel Number Nine

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,842, price is now $1,309 per person
$1,309
per person
Jan 29 - Feb 4
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
19.2/10 Exceptional! (1,002 reviews)
Staff and front desk were really friendly and helpful . Hotel was clean , very homely energy also . Safe with the doorman there sometimes. Spa has a sauna steam cold plunge . Thankyou for a lovely time.

Reviewed on Nov 10, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $3,577, price is now $2,549 per person
$2,549
per person
Jan 29 - Feb 4
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
20/10 Exceptional! (3 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Pienza
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Discover the most popular places to visit in Pienza

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.

Pienza Cathedral

Palazzo Piccolomini

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.

Palazzo Piccolomini

Piazza Pio II

After visiting Piazza Pio II, make a plan to see the other sights and activities in Pienza. While you're here, you can savor the wineries.

Piazza Pio II

What to do in Pienza

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$52
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Olive Oil Tours and Tasting at Frantoio di Montalcino

Olive Oil Tours and Tasting at Frantoio di Montalcino

$58
per adult
Olive Oil Tours and Tasting at Frantoio di Montalcino
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
See all activities in Pienza

Pienza Hotel Deals

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26 Pienza SI
8.6/10 Excellent! (610 reviews)
The room was beautiful and very clean. Breakfast staff was very kind.

Reviewed on Oct 29, 2025

Get rates
Hotel Relais II Chiostro di Pienza
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $160 total per night from Nov 21 to Nov 22
$160 total
Nov 21 - Nov 22
Total with taxes and fees
9.2/10 Wonderful! (133 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

Hotel San Gregorio
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $136 total per night from Nov 30 to Dec 1
$136 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (323 reviews)
Perfect stay

Reviewed on Oct 17, 2025

Hotel Corsignano
See all 6,052 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.

Find the Best Pienza Vacation Packages

Pienza Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
1,250
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Pienza Cathedral, Terme di Montepulciano Spa and Piscine Termali Theia

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from $653 on Expedia. However, how much your vacation to Pienza costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Pienza?
If you're looking to score a cheap Pienza vacation package, consider traveling in March, November and December. You'll usually find lower rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Pienza?
Typically, a handful of days is enough to visit the major attractions during your Pienza vacation. But if you want to have more time to rest or go on day trips, consider extending your trip.
Is it worth booking a vacation package to Pienza?
Well known for its views, hiking and festivals, a Pienza vacation is a hit with all kinds of visitors. Be sure to check out major sights like Pienza Cathedral and Palazzo Piccolomini, and consider renting a car for day trips to discover even more.
How to find the best Pienza package deals?
Use Expedia's filter tool to find some great Pienza package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Pienza package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Pienza vacation as a package?
You can enjoy significant savings on your Pienza retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pienza?
If you have your Pienza travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Pienza?

  1. Pick your travel dates: What you plan to do in Pienza and your favorite season will help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Pienza.
  3. Use Expedia's trip planning tool to explore Pienza: Research every part of your trip to Pienza with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the sights and activities you'd like to experience in Pienza. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Pienza vacation package that brings all your bookings together.
  6. Book any day trips or activities: Here's the fun part — locking in everything you want to do and see. Check out some of the exciting things to do in Pienza and reserve your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Pienza vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Pienza vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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