Pienza Vacations from $702

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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.

The Latest Pienza vacation packages

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

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,144, price is now $702 per person
$702
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
Our stay was lovely, very comfortable, small but good choice of breakfast. Beds were comfy and room was clean when we arrived and cleaned everyday. I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.

Reviewed on Aug 19, 2025

Arte' Boutique Hotel

Arte' Boutique Hotel

4 out of 5
Historic Centre of Florence
Price was $1,417, price is now $1,005 per person
$1,005
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (283 reviews)
Staff were really friendly, including making sure we were attended to even during a blackout

Reviewed on Aug 10, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,170, price is now $707 per person
$707
per person
Nov 11 - Nov 17
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
The room that we used for 5 nights was filthy.and dusty. The shower was very small, barely squeeze in. The interior was outdated with only one point to recharge phones and the cupboards were broken. The door to the room required force to open and close. Location is convenient close to transport.

Reviewed on Aug 23, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,303, price is now $798 per person
$798
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (469 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

Collegio alla Querce - Auberge Resorts

Collegio alla Querce - Auberge Resorts

5 out of 5
Le Cure
Save 100% on your flight
Price was $4,920, price is now $3,023 per person
$3,023
per person
Nov 11 - Nov 17
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (2 reviews)
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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

Capturing the best version of yourself with beautiful professional pictures

Photography Guided Tour in the Heart of Val D'Orcia and Tuscany

$290
per traveler
Photography Guided Tour in the Heart of Val D'Orcia and Tuscany
Pienza: Private Walking Tour in the Heart of Tuscany

Pienza: Private Walking Tour in the Heart of Tuscany

$380
per traveler
Pienza: Private Walking Tour in the Heart of Tuscany
Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

$209
per adult
Pienza & Montepulciano Small Group Tour from Siena
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
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Aug 26 to Aug 27
$129 total
Aug 26 - Aug 27
Total with taxes and fees
8.6/10 Excellent! (584 reviews)
"Great experience"

Reviewed on Aug 13, 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
$137 nightly
The price is $158 total per night from Aug 27 to Aug 28
$158 total
Aug 27 - Aug 28
Total with taxes and fees
9.4/10 Exceptional! (303 reviews)
"Very close to city center. Nice view from hotel room"

Reviewed on Aug 20, 2025

Hotel Corsignano
Tenuta Santo Pietro

Tenuta Santo Pietro

Localita Santo Pietro 29, Pienza, SI
$213 nightly
The price is $240 total per night from Sep 24 to Sep 25
$240 total
Sep 24 - Sep 25
Total with taxes and 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 6,215 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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Frequently asked questions

How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from $702 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.