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Top Pienza hotels

Agriturismo Poggio Tobruk

Agriturismo Poggio Tobruk

Loc. Spedaletto Poggio Tobruk Pienza SI
This farm stay doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
"Perfect location to tour the surrounding hill towns and wineries. The host has connections and can make you last minute reservations for dinner and wineries."

Reviewed on Sep 13, 2026

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Opens in a new windowAgriturismo Poggio Tobruk
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
$620 nightly
The price is $691 total per night from Oct 26 to Oct 27
$691 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and airport ...
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"

Reviewed on Oct 5, 2026

Opens in a new windowVilla di Piazzano - Small Luxury Hotel of the World
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
$135 nightly
The price is $153 total per night from Nov 5 to Nov 6
$153 total
Nov 5 - Nov 6
Total with taxes and fees
An attached winery and an outdoor pool are featured at this hotel. Families will appreciate the playground, onsite laundry facilities, and babysitting. There's ...
"We stayed at the olive Farmhouse across the street from the main property. Rooms were cozy and clean with some interesting toiletries to use (made from olive oil). The property also has a range of activities (extra) to choose from. Just a note that eventhough the farmhouse is close to the main property, ..."

Reviewed on Oct 6, 2026

Opens in a new windowAgriturismo Il Macchione
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
$869 nightly
The price is $963 total per night from Oct 11 to Oct 12
$963 total
Oct 11 - Oct 12
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Family-friendly amenities include a playground and in-room childcare. ...
"Great, peaceful place to stay. Gorgeous property with pools and spa. Could use another food option but otherwise excellent."

Reviewed on Oct 7, 2026

Opens in a new windowPrecise Tale Poggio Alla Sala
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
$129 nightly
The price is $149 total per night from Nov 8 to Nov 9
$149 total
Nov 8 - Nov 9
Total with taxes and fees
This residence features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public ...
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"

Reviewed on Oct 8, 2026

Opens in a new windowHotel San Gregorio
La Bandita Townhouse

La Bandita Townhouse

111 Corso Rossellino Pienza SI
Fully refundableReserve now, pay when you stay
$395 nightly
The price is $438 total per night from Nov 4 to Nov 5
$438 total
Nov 4 - Nov 5
Total with taxes and fees
This property features a full-service spa and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, ...
"Great 12 room boutique hotel in the heart of Pienza."

Reviewed on Sep 28, 2026

Opens in a new windowLa Bandita Townhouse
Podere Spedalone

Podere Spedalone

1 out of 5
Strada per Cosona SP71 Pienza SI
$154 nightly
The price is $174 total per night from Oct 30 to Oct 31
$174 total
Oct 30 - Oct 31
Total with taxes and fees
A restaurant and a seasonal outdoor pool are featured at this farm stay. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and ...
"Disappointing and Overpriced We stayed three nights and were very disappointed. Access requires driving at least 2 km on a poorly maintained, extremely dusty gravel road. Parking is at the top of a steep hill, making access difficult. The small unloading area near the rooms was often occupied by ..."

Reviewed on Oct 9, 2026

Opens in a new windowPodere Spedalone
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $159 total per night from Nov 8 to Nov 9
$159 total
Nov 8 - Nov 9
Total with taxes and fees
This smoke-free hotel features 2 hot tubs, a restaurant, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, ...
Opens in a new windowHotel Corsignano
Tenuta Santo Pietro

Tenuta Santo Pietro

Localita Santo Pietro 29 Pienza SI
$213 nightly
The price is $239 total per night from Oct 20 to Oct 21
$239 total
Oct 20 - Oct 21
Total with taxes and fees
An attached winery and a restaurant are featured at this smoke-free farm stay. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free ...
Opens in a new windowTenuta Santo Pietro
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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.

Pienza Hotel & Travel Guide

If you're seeking nice hotel establishments in the area around Pienza, it's good to know that there are many different options on offer. With the assistance of our comprehensive booking pages, you can research 77 accommodation choices within a 6-mile (10-kilometer) radius of the heart of Pienza.

Pienza's downtown area is a morning stroll from Travelocity-listed rooms like Hotel Corsignano and Piccolo Hotel La Valle.

The Palazzo Piccolomini and the Cathedral of Pienza are well-liked Pienza attractions and many travelers choose to book accommodation in the surrounding area. The Hotel Relais II Chiostro di Pienza and the Antica Locanda are two of the hotels that are in the vicinity of the Palazzo Piccolomini. The Albergo Rutiliano and the B&B Il Rossellino City View are close to the Cathedral of Pienza.

More economical places to stay in and around the Pienza region are Albergo Rutiliano, Agriturismo Torre Vecchia and B&B Il Rossellino City View.

It's worth checking out the Castello di Velona SPA Resort & Winery along with the Adler Thermae Spa & Wellness Resort. The Castello di Velona SPA Resort & Winery is located just 10 miles (16 kilometers) away from the main part of Pienza. The Adler Thermae Spa & Wellness Resort, is situated only 4 miles (7 kilometers) away. Other possible hotels and apartment options are the Fonteverde and the Villa Armena.

Once you have spent some time in Pienza, why not explore a bit further afield? The Tuscany region is home to plenty of attractions. Discover Tuscany's ruins and also photograph the area's rural landscapes, beaches and coastal plains. Common activities in this particular region of Italy include snowboarding, skiing and snow shoeing.

40 miles (61 kilometers) from Pienza, you can find Val d'Elsa, which is where you'll find Archeological and Collegiate Church Museum and Torre Rognosa. The Tenuta Di Mensanello and Torraccia di Chiusi are just some of the convenient accommodation options in Val d'Elsa. 6 miles (10 kilometers) southwest of Pienza, you'll reach Val d'Orcia, home to the Hotel Osteria Dell Orcia and Locanda del Loggiato. While visiting Val d'Orcia, be sure to visit the Collegiate Church of San Quirico and Palazzo Chigi.

Peretola Airport is a convenient arrival point for air travel, and is found 55 miles (91 kilometers) outside the heart of Pienza. Conveniently located hotels are The St. Regis Florence and The Westin Excelsior, Florence.

Frequently asked questions

What are the top kid-friendly hotels in Pienza?
From thoughtful amenities to bigger rooms, kid-friendly hotels are equipped with features that can help turn a great family vacation into an incredible one. These Pienza properties make vacationing with children a breeze: Hotel Relais II Chiostro di Pienza will help make your getaway the most memorable one yet. It offers plenty of nice little touches, such as a swimming pool and complimentary breakfast. Also consider Il Giardino Segreto. It comes with complimentary breakfast, pet-friendly facilities and lots of opportunities to hang out together.
Where can I find cheap hotels in Pienza?
At Travelocity you'll find really nice hotels in Pienza at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Pienza rather than in Pienza. We may find you even better rates, too.
How do I find the best Pienza hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Pienza then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Pienza?
The cheapest hotel in Pienza is $149. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Pienza?
There are 6,017 hotels in Pienza on Travelocity.
What are the best hotels in Pienza?
Pienza has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Pienza for you!
When is the best time to visit Pienza?
If you want the joy of a fun-filled trip in peak season, visit Pienza during February, May and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as March, November and December.
When is the cheapest time to stay in Pienza?
Based on historic data is usually the cheapest month to visit Pienza. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Pienza?
There are multiple hotels in Pienza that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Pienza. We have plenty of kid-friendly hotels in Pienza to choose from on Travelocity!
Why book a hotel in Pienza through Travelocity?
Because we have the top hotels in Pienza! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Pienza on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Pienza hotel reviews by fellow wanderers

Hotel San Gregorio

Hotel San Gregorio

4 out of 5
Posted 1 day ago
Travelocity Verified Review
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
A verified traveler stayed at Hotel San Gregorio
Hotel San Gregorio

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