Pienza Vacations from $1,122
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Pienza Vacation Packages
- Aurum Firenze
Oct 15 - Oct 20Aurum Firenze + Flight
Historic Centre of Florence4 nights4.0 star property7.4/10 - Good (1,001 reviews)Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,565$1,122found 1 day agoper traveler - Aurum Uffizi
Oct 15 - Oct 20Aurum Uffizi + Flight
Historic Centre of Florence4 nights4.0 star property7.6/10 - Good (1,001 reviews)"Everything was really good!👍"Reviewed July 24, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,726$1,157found 1 day agoper traveler - Hotel La Scaletta Al Ponte Vecchio
Oct 15 - Oct 20Hotel La Scaletta Al Ponte Vecchio + Flight
Historic Centre of Florence4 nights4.0 star property9.0/10 - Wonderful (1,000 reviews)"Never stayed in a palace! What an experience! Everything was 100% or more!"Reviewed July 21, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,955$1,363found 1 day agoper traveler - Bernini Palace
Aug 23 - Aug 29Bernini Palace + Flight
Historic Centre of Florence5 nights5.0 star property9.8/10 - Exceptional (1,003 reviews)"The hotel was beautiful. It was clean. The staff was wonderful. The breakfast was unbelievable so great the great they had a great bar. Hotel was wonderful the bathroom it was just beautiful. You stayed there last year and we stayed there again this year and if I ever go back to Florence again, this is where I would want to stay and that’s it thank you bye bye-bye"Reviewed July 24, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$2,242$1,613found 1 day agoper traveler - The Moon Boutique Hotel & Spa
Aug 23 - Aug 29The Moon Boutique Hotel & Spa + Flight
Historic Centre of Florence5 nights4.0 star property9.6/10 - Exceptional (577 reviews)"The hotel was very well-maintained with helpful staff. The breakfast was fantastic. The only problem was, it was a far walk to the city centre. Despite the walk , I highly recommend this hotel"Reviewed July 20, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,632$1,234found 1 day agoper traveler
Discover the most popular places to visit in Pienza
What to do in Pienza
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano Wine Tasting in the Tuscan Countryside
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Pienza Hotel Deals
PienzaLettings Suites
PienzaLettings Suites
TuscanyLettings Studio&Room
TuscanyLettings Studio&Room
Rossellino
Rossellino
Tenuta Santo Pietro
Tenuta Santo Pietro
Agriturismo Il Macchione
Agriturismo Il Macchione
Casa Gioia - Casa Olivieri
Casa Gioia - Casa Olivieri
Frequently Asked Questions
How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from $1,122 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?
- Pick your travel dates: What you plan to do in Pienza and your favorite season will help you decide when to go.
- 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.
- 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.
- 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.
- 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.
- 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
Book with confidence
Things to do in and around Pienza
Pienza, nestled in Tuscany, is perfect for outdoor and romantic getaways, offering a range of activities for visitors. Enjoy rejuvenating spa treatments, unwind at a private country club, or embark on delightful wine tours. The picturesque picnic areas provide a lovely setting for relaxation, while the charm of the town invites exploration. Don't miss the opportunity to experience the unique culture and scenic beauty of Pienza during your visit.
Shopping
For unique souvenirs, visit RI Crea RE in Pienza for local crafts. If you're up for a drive, Valdichiana Outlet Village, located 12 miles away, offers a variety of brands and family-friendly entertainment. Pinzi Pinzuti, 14 miles away, is another charming spot for gifts.
Recreation
Experience luxury at the Chapel of our Lady of Vitaleta, a serene country club just 2 miles from Pienza. Unwind at Terme di Chianciano, a soothing spa 7 miles away, or indulge in rejuvenating treatments at San Giovanni Terme Rapolano, located 15 miles from Pienza.
Adventure
The Macinaie Ski Lift, located 13 miles from Pienza, offers thrilling skiing experiences amidst stunning alpine scenery. For adrenaline-pumping karting, visit the Siena Circuit, 19 miles away. Alternatively, the Saltalbero Adventure Park, 15 miles from Pienza, features exciting zip lines and rope courses for an outdoor adventure.
Nightlife
Pienza's nightlife offers a charming blend of cozy wine bars and local taverns. Visit Bar di Pienza for a delightful aperitivo and enjoy the warm atmosphere. For a more lively scene, head to La Bottega di Pienza, where you can savor local wines and mingle with friendly locals.
Find the best attractions in and around Pienza
Pienza, a charming town in Tuscany, is perfect for outdoor and romantic getaways. Explore the stunning piazza, visit the historic monastery, or relax in natural hot springs. This destination offers a rich cultural experience with attractions like the Pienza Cathedral and various outdoor activities. Whether you’re on a trip to Pienza for its scenic beauty or unique local experiences, you'll find plenty to enjoy in this picturesque town.
- Pienza Cathedral: Nestled in the heart of Pienza, this stunning cathedral showcases Renaissance architecture and offers a serene atmosphere. Explore its beautifully adorned interior and soak in the cultural vibes that make it a must-visit.
- Piazza Grande: Located 5 miles from Pienza, Piazza Grande is a bustling square that embodies the essence of local life. Surrounded by charming cafes and shops, it’s the perfect spot to experience the vibrant culture and city vibes of the region.
- Terme di Montepulciano Spa: Just 6 miles away, this luxurious hot spring offers a tranquil retreat. Enjoy wellness and relaxation in beautiful outdoor settings, making it an ideal place to unwind and rejuvenate.
Best time to go to Pienza
The best time to visit Pienza can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pienza falls in July and August. August has slightly high visitor numbers and sunny weather. The coolest average temperature in Pienza falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.
Tips to save on your trip to Pienza
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Pienza.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.