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Pienza Vacations

Pack those stellar shades. We have Pienza vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Pienza – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Pienza vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Pienza

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Pienza vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Pienza well.

Top Hotel Deals

See all 1,622 Hotels in Pienza
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26, Pienza
4.5 out of 5.0

Situated in Pienza, this romantic hotel is steps from Piazza Pio II, Pienza Cathedral, and Palazzo Piccolomini. Palazzo Comunale and Enoteca Di Ghino are also ...

Hotel Corsignano

Hotel Corsignano

Via Della Madonnina 11, Pienza
4.5 out of 5.0

Situated in Pienza, this hotel is within a 10-minute walk of RI Crea RE, Pienza Cathedral, and Palazzo Piccolomini. Enoteca Di Ghino and Palazzo Comunale are ...

$80

$80
Hotel Residence San Gregorio

Hotel Residence San Gregorio

Via Della Madonnina 4, Pienza
3.5 out of 5.0

Located in the heart of Pienza, this residence is within a 5-minute walk of RI Crea RE and Pienza Cathedral. Palazzo Piccolomini is 0.3 mi (0.5 km) away.

$89

$89
Antica Locanda

Antica Locanda

Corso Il Rossellino, 72, Pienza

Situated in the historical district, this townhouse accommodation is steps from Palazzo Comunale, Pienza Cathedral, and Palazzo Piccolomini. Palazzo Borgia and ...

$82

$82
L'Olmo

L'Olmo

SP 88 Orcia delle Macchie, Pienza

Situated in Pienza, this townhouse accommodation is within 3 mi (5 km) of Art Studio di Adelina Quadri, Pienza Cathedral, and Palazzo Piccolomini. Palazzo Borgia ...

La Bandita Townhouse

La Bandita Townhouse

111 Corso Rossellino, Pienza
Tenuta Santo Pietro

Tenuta Santo Pietro

Localita Santo Pietro 29, Pienza

Situated in Pienza, this farm stay is within 6 mi (10 km) of RI Crea RE, Pienza Cathedral, and Palazzo Piccolomini. Enoteca Di Ghino and Piazza Pio II are also ...

B&B Camere La Vite

B&B Camere La Vite

Via Dogali, 29, Pienza

Located in the heart of Pienza, this townhouse accommodation is steps from Palazzo Comunale and Pienza Cathedral. Palazzo Piccolomini is 0.2 mi (0.4 km) ...

$113

$113
Agriturismo Bonello

Agriturismo Bonello

Strada Provinciale 146, Pienza

Situated in Pienza, this farm stay is 2.6 mi (4.3 km) from Horti Leonini and 3 mi (4.8 km) from Pienza Cathedral. Collegiate Church of San Quirico and Palazzo ...

Pienza

Pienza

Loc Piandimaggio, Pienza

Situated in Pienza, this apartment building is within 6 mi (10 km) of Art Studio di Adelina Quadri, Palazzo Piccolomini, and Pienza Cathedral. Pieve di Corsignano ...

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.