Explore top 2025 4 Star Hotels in Pienza

Name: Hotel San Michele
Rating: 9

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Top Pienza 4 Star hotels

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26 Pienza SI

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and free perks like continental breakfast and WiFi in ...

8.6/10 Excellent! (610 reviews)

The room was beautiful and very clean. Breakfast staff was very kind.

Reviewed on Oct 29, 2025

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Hotel Certosa Di Maggiano

Strada di Certosa, 82/86 Siena SI

Fully refundableReserve now, pay when you stay

$198 nightly

$222 total

Dec 9 - Dec 10

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's fun for all ages with a playground and an arcade/game room, and families will appreciate ...

9.8/10 Exceptional! (180 reviews)

Hotel with amazing installation, service and great location.

Reviewed on Nov 23, 2025

Grand Hotel Terme

Piazza Italia, 8 Chianciano Terme SI

$80 nightly

$93 total

Nov 27 - Nov 28

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a children's ...

7.8/10 Good! (61 reviews)

Old but maintained well. Quiet and easy

Reviewed on Aug 29, 2025

Hotel Corsignano

Via Della Madonnina 11 Pienza SI

$117 nightly

$136 total

Nov 30 - Dec 1

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, ...

9.4/10 Exceptional! (324 reviews)

Amazing hotel completely walkable to all pienza has to offer. The breakfast is amazing. The room was so pretty. The jacuzzi topped of a perfect day

Reviewed on Nov 20, 2025

Precise House Montaperti Siena

Str. di Poggio al Vento 1/A Asciano SI

$75 nightly

$90 total

Dec 22 - Dec 23

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and ...

8.2/10 Very Good! (590 reviews)

Queen bed

Lovely staff. Misleading advertisement regarding queen bed and single bed in the apartment. There are 2 single beds and a pull out couch.

Reviewed on Sep 21, 2025

Abbadia Sicille Relais

SP 14 Loc. Abbadia Sicille Trequanda SI

Fully refundableReserve now, pay when you stay

$71 nightly

$82 total

Nov 30 - Dec 1

Total with taxes and fees

This residence features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...

8.8/10 Excellent! (159 reviews)

We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone

Reviewed on Nov 4, 2025

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

Via Poliziano 18 San Quirico d'Orcia SI

$146 nightly

$167 total

Nov 27 - Nov 28

Total with taxes and fees

A full-service spa and a restaurant are featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...

9.2/10 Wonderful! (220 reviews)

THE AMAZING LOCATION THE VIEWS OF THE MOUNTAINS AND VALLEYS AND AMAZING POOL (WE DID NOT GET TO USE IT BECAUSE DUE TO THE TEMPERATURE BEING IN THE 60'S) THE RESTAURANT WHICH IS THE NEXT TO THE HOTEL WAS GREAT !!!

Reviewed on Oct 29, 2025

Grand Hotel Admiral Palace

Via Umbria 2 Chianciano Terme SI

Fully refundableReserve now, pay when you stay

$140 nightly

$159 total

Dec 5 - Dec 6

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 5 conference rooms, ...

8/10 Very Good! (302 reviews)

The staff was very helpful and nice. Safe neighborhood and quiet.

Reviewed on Jun 29, 2025

Borgo Il Melone

Case Sparse, 38 Cortona AR

This hotel features 20 poolside bars, a bar/lounge, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...

Not to be missed!

We were initially uncertain about booking here due to some negative online comments; however, very happy we did! it would be difficult to pristinely maintain the property as it is historic and quite large, so if you’re looking for something with every modern amenity, this is not the stay for you. ...

Reviewed on Sep 19, 2024

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Hotel San Michele

Via Guelfa 15 Cortona AR

An area shuttle and a shopping center shuttle are featured at this hotel, along with a bar/lounge. WiFi in public areas is free. Traveling on business? Take ...

9/10 Wonderful! (270 reviews)

Very friendly and helpful staff. Nice rooms

Reviewed on Sep 7, 2025

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4 Star Hotels Pienza

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Pienza 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Pienza will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Pienza, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.