A historic square with a prominent tower and statues.

Winery Hotels & Resorts in Pienza from AU$166

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Check availability on Pienza Winery Hotels

Tonight
21 Sept - 22 Sept
Tomorrow
22 Sept - 23 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Pienza hotels with winery

A hotel room with a bed, a desk, a chair, and a television.
A room with a sofa, a bed, a table, and a view of the outdoors.
A buffet setup with various food items and utensils.
A historic town with a prominent church, a courtyard with a swimming pool, and terraced buildings.

1. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
Brazil
ettore
AU$213
includes taxes & fees
4 Oct - 5 Oct
Relais Cloister Pienza
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a gravel pathway leading to the entrance.
A stone building with a tiled roof, surrounded by a grassy area and flowering plants.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

2. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
United States
Nathan
AU$346
includes taxes & fees
15 Oct - 16 Oct
Agriturismo Il Macchione
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.
A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A building with a symmetrical facade, a central entrance, and a fountain in the courtyard.

3. Hotel San Gregorio

Hotel San Gregorio
Pienza
United States
Nancy
AU$345
includes taxes & fees
20 Oct - 21 Oct
Hotel San Gregorio
Two people sitting at a round table outdoors with a scenic view of mountains in the background.
A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.
A breakfast buffet with various food items and beverages.
A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

4. Hotel Corsignano

Hotel Corsignano
Pienza
United States
shane
AU$295
includes taxes & fees
19 Oct - 20 Oct
Hotel Corsignano
A narrow alleyway with stone walls and a brick floor, leading to a building with windows and balconies.
A couple on a balcony overlooking a historic town with terracotta roofs and a prominent clock tower.
A hallway with an arched doorway leading to a bedroom with a bed and a dresser.
A reception desk with a 'RECEPTION' sign, a computer monitor, a plant, and a cash register.

5. Rossellino

Rossellino
Pienza
United States
Darrell
AU$189
includes taxes & fees
8 Oct - 9 Oct
Rossellino
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.
A bedroom with a four-poster bed, a wooden chest, a desk with a chair, and a window with blue curtains.
A wooden door with a sign, a staircase with blue steps, and a metal handrail.
A room with a view of a historic town, featuring stone buildings and a clear sky.

6. PienzaLettings Suites

PienzaLettings Suites
Pienza
United States
Pearlyn
AU$166
includes taxes & fees
18 Oct - 19 Oct
PienzaLettings Suites
A cozy room with a fireplace, two armchairs, and a table.
A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.
A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

7. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
United States
Robert
AU$358
includes taxes & fees
21 Oct - 22 Oct
Tenuta Santo Pietro
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.
A wooden desk with two chairs, each with a white cushion. The desk has a drawer and a small decorative item on top.
A staircase with a handrail leading to a door with a blue handle.
A dining area with a table and chairs, a staircase leading to an upper level, and a wooden door.

8. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
Brazil
Lucas
AU$177
includes taxes & fees
1 Oct - 2 Oct
TuscanyLettings Studio&Room
A modern interior with a stone wall, wooden paneling, and a television.
A villa with a tower, a swimming pool, and a well-maintained garden.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.
A dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.

9. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
United States
Marie
AU$315
includes taxes & fees
28 Sept - 29 Sept
Hotel Rutiliano Centro Benessere
A stone building with a wooden door, a staircase, and a small window with a metal grill.
A bedroom with a large bed, two bedside tables, a wooden wardrobe, and two wall-mounted lights.
A narrow street with buildings on either side, featuring balconies and potted plants.
A kitchen with a dining table set for two, a gas stove, and a potted plant on the wall.

10. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
United States
Nancy
AU$186
includes taxes & fees
12 Oct - 13 Oct
Casa Gioia - Casa Olivieri
View all properties

Top Pienza Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 1 day ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Quaint but modern hotel walking distance to all - good breakfast and service in hotel restaurant. Spacious rooms with air conditioning (which gets turned off when staff cleans room - call desk to turn back on), safe, and bathroom with tub- but no shower curtain- took a while to learn how to negotiate using the shower handle. Pool area is restful. Enjoyed our stay"
JANET 3-night trip
Posted 4 days ago
Hotel San Gregorio
Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"Beautiful place to stay halfway between Pienza and Montepulciano. The food was some of the best we had during our entire time in Italy and we loved spending our afternoon by the pool with a drink."
Jenny 2-night trip
Posted 6 days ago
Tenuta Santo Pietro
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Very warm and friendly service."
Abdel 2-night trip
Posted 9 days ago
Castiglion del Bosco, A Rosewood Hotel
La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Fantastic venue! Loved Pienza! The Inn was beautiful and the staff extremely friendly and welcoming. We would love to go back"
Ross 1-night trip
Posted 3 weeks ago
La Bandita Townhouse

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