A town with terracotta-roofed buildings and a distant church.

Piancastagnaio Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Piancastagnaio vacation rentals

A modern kitchen with a round dining table, black cabinetry, and a large clock on the wall.

1. Affittacamere I Canneggiatori

Affittacamere I Canneggiatori
Abbadia San Salvatore
8.6 out of 10, Excellent, (9 reviews)
"Very stylish, modern, well equipped apartment. Close to everything. Bed is okay, had a relaxing sleep. Good size bathroom with toilet. Staff who came to clean daily was very helpful, supportive, kind. Parking on the street in from of the building. "
United Kingdom
Erika
Affittacamere I Canneggiatori
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

2. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (20 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is P4,544
P5,139 total
includes taxes & fees
Nov 4 - Nov 5
FonteLiving
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

3. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (161 reviews)
"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"
United States
Julia
The price is P8,143
P9,380 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
A poolside area with two glasses of water, candles, and a stone pathway.

4. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is P10,687
P12,037 total
includes taxes & fees
Oct 12 - Oct 13
Casanova - Panoramic Rooms and Suites
A pool with a waterfall feature and a stone sculpture.

5. Villaggio Le Querce

Villaggio Le Querce
4.0 star property
Sorano
9.0 out of 10, Wonderful, (64 reviews)
"The smaller, children, pool is further away and down many stairs. There are many comfortable seats by the main pool. I wish the main pool had a variation in depth.Breakfast is heavenly. All the staff we encountered were very friendly."
United States
Nathan
The price is P5,120
P5,983 total
includes taxes & fees
Oct 20 - Oct 21
Villaggio Le Querce
A room with a curved ceiling, a hot tub, and a glass door leading outside.

6. Chalet Il Cristallo

Chalet Il Cristallo
Castel del Piano
7.6 out of 10, Good, (4 reviews)
"Camera impeccabile, personale cortese e disponibile, colazione ottima ,come la cena. Struttura molto accogliente. Ottima per famiglie."
Italy
Federico
The price is P3,068
P3,586 total
includes taxes & fees
Oct 11 - Oct 12
Chalet Il Cristallo
A stone archway leading to a dining area with a table set for two, overlooking a lush green landscape.

7. Agriturismo Poggio Monte

Agriturismo Poggio Monte
Manciano
9.8 out of 10, Exceptional, (14 reviews)
" Great place and staff"
United States
Tomas
The price is P6,615
P7,488 total
includes taxes & fees
Oct 20 - Oct 21
Agriturismo Poggio Monte
A crowded restaurant with brick walls and multiple tables and chairs.

8. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (150 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is P11,632
P13,077 total
includes taxes & fees
Nov 3 - Nov 4
La Locanda di San Francesco
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

9. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (10 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is P14,425
P16,572 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo Saloni
A natural hot spring with multiple pools and people swimming.

10. Il Cantuccio

Il Cantuccio
Manciano
9.2 out of 10, Wonderful, (62 reviews)
"very warm and welcoming. I do recommend having a phone with roaming access so you can receive your instructions to access."
Australia
Eugenio
The price is P4,645
P5,320 total
includes taxes & fees
Oct 11 - Oct 12
Il Cantuccio
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

11. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is P7,697
P9,030 total
includes taxes & fees
Nov 8 - Nov 9
Corte Francigena - Apartments
Living area

12. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is P7,076
P8,064 total
includes taxes & fees
Oct 18 - Oct 19
montorio
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

13. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (134 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is P14,496
P16,227 total
includes taxes & fees
Nov 2 - Nov 3
Il Tosco
A kitchen with wooden cabinets, a tiled floor, a dining table with chairs, and a small archway leading to another room.

14. La Dimora di Dida

La Dimora di Dida
Seggiano
The price is P5,062
P5,568 total
includes taxes & fees
Nov 1 - Nov 2
La Dimora di Dida
A patio area with outdoor seating, potted plants, and a view of the landscape.

15. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (70 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is P6,817
P9,249 total
includes taxes & fees
Oct 12 - Oct 13
Affitacamere Maria Gabriella
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

16. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is P7,606
P8,648 total
includes taxes & fees
Nov 2 - Nov 3
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

17. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is P28,123
P31,216 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

18. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is P6,616
P7,558 total
includes taxes & fees
Nov 1 - Nov 2
Bed & Breakfast Vicolo dell'Oste
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

19. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is P8,633
P9,777 total
includes taxes & fees
Oct 19 - Oct 20
B&B Le Scalette di Piazza
An interior courtyard with stone columns, arches, and a mosaic.

20. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is P10,019
P11,302 total
includes taxes & fees
Oct 14 - Oct 15
Meublé Il Riccio
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.
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Top Piancastagnaio Hotel Reviews

Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"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"
Julia 2-night trip
Posted 16 hours ago
Hotel San Gregorio

Find out more about Piancastagnaio

Search for holiday rentals in Piancastagnaio on Expedia! You can easily find your home rentals, villas, holiday apartments in Piancastagnaio using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Piancastagnaio?

Yes, there are vacation rentals near popular local attractions in Piancastagnaio, or you can select a secluded option if you want a relaxing place to stay.

How many vacation rentals will I find in Piancastagnaio?

Choose from 5 Expedia vacation rentals in Piancastagnaio for a memorable vacation.

What’s there to see and do in Piancastagnaio?

Explore the area and family-friendly sights such as Villa Acquaviva - La Fattoria, or get out into nature at a spot like Monte Amiata. In the larger area, you’ll find Abbazia di San Salvatore and Baths of San Filippo.

What’s a vacation rental in Piancastagnaio like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Piancastagnaio. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.