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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Piancastagnaio vacation rentals

A covered outdoor seating area with brick pillars, potted plants, and a view of trees and mountains.

1. Holiday Home 'Casale I Cascetti' with Pool, Garden and Wi-Fi

Holiday Home 'Casale I Cascetti' with Pool, Garden and Wi-Fi
Siena
10.0 out of 10, Exceptional, (1 review)
"Bellissime camere, dotate di ogni confort, immerse nel verde della campagna toscana. Camere spaziose, comode, luminose e attrezzate di tutto. Proprietari ospitali e gentili, sempre pronti a fornire indicazioni. Grazie di tutto , torneremo senz'altro!"
United States
Annarosa m.
The price is CA $1,031
CA $1,038 total
includes taxes & fees
Oct 22 - Oct 23
Holiday Home 'Casale I Cascetti' with Pool, Garden and Wi-Fi
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, (21 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is CA $108
CA $122 total
includes taxes & fees
Nov 8 - Nov 9
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, (165 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is CA $179
CA $207 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
A pool with a waterfall feature and a stone sculpture.

4. 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 CA $115
CA $135 total
includes taxes & fees
Oct 22 - Oct 23
Villaggio Le Querce
A room with a curved ceiling, a hot tub, and a glass door leading outside.

5. 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 CA $66
CA $77 total
includes taxes & fees
Oct 27 - Oct 28
Chalet Il Cristallo
A stone house with a swimming pool at dusk.

6. Large apartment with garden in an old farmhouse with swimming pool

Large apartment with garden in an old farmhouse with swimming pool
Radicofani
10.0 out of 10, Exceptional, (1 review)
"Pietreta è un angolo di paradiso. Verde e querce secolari. Camere pulitissime. Appartamento super fornito. Radicofani è un paesino delizioso. Al centro della Val d'Orcia. Vicino alle note località termali. In questa zona si mangia bene e si beve meglio 😊😊😊"
Italy
TINA G.
The price is CA $190
CA $196 total
includes taxes & fees
Oct 21 - Oct 22
Large apartment with garden in an old farmhouse with swimming pool
A stone building with a wooden door, steps leading to a balcony, and potted plants.

7. The Old Washhouse

The Old Washhouse
Radicofani
10.0 out of 10, Exceptional, (2 reviews)
"What a wonderful stay! This apartment was absolutely perfect for the two of us. It was impeccably clean, warm, cozy, and spacious enough for a couple. The bed and furniture was so comfortable, and the attention to detail was simply spot on. Everything was absolutely perfect!We were so touched by the thoughtful complimentary coffee, tea, and breakfast items. The bathroom was just as equipped with shampoo and soaps. Every little detail made us feel right at home.The gorgeous private garden was a...
Canada
Chantale M.
The price is CA $141
CA $210 total
includes taxes & fees
Oct 26 - Oct 27
The Old Washhouse
A poolside area with two glasses of water, candles, and a stone pathway.

8. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (102 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is CA $253
CA $285 total
includes taxes & fees
Oct 21 - Oct 22
Casanova - Panoramic Rooms and Suites
A natural hot spring with multiple pools and people swimming.

9. Il Cantuccio

Il Cantuccio
Manciano
9.2 out of 10, Wonderful, (62 reviews)
"The breakfast was good, they had a few different kinds of options of breads, pastries, coffee, toppings for bread, and other things."
United States
Mara
The price is CA $105
CA $120 total
includes taxes & fees
Oct 21 - Oct 22
Il Cantuccio
A stone building with a tiled roof, a staircase leading to a lower level, and a garden with various plants.

10. Double bedroom with private bathroom, private access, garden and swimming pool

Double bedroom with private bathroom, private access, garden and swimming pool
Radicofani
The price is CA $127
CA $133 total
includes taxes & fees
Oct 22 - Oct 23
Double bedroom with private bathroom, private access, garden and swimming pool
An open door leading to a balcony with a view of a forested hillside.

11. La Dimora di Dida

La Dimora di Dida
Seggiano
The price is CA $99
CA $109 total
includes taxes & fees
Oct 21 - Oct 22
La Dimora di Dida
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

12. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
Bagni San Filippo
10.0 out of 10, Exceptional, (1 review)
"Terme House is just as described. It had all of the amenities mentioned and was clean. We wanted a place just off ss2 - perfect location and quiet town. 5 stars!!!"
United States
Lori
The price is CA $157
CA $223 total
includes taxes & fees
Oct 21 - Oct 22
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

13. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is CA $310
CA $357 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Saloni
A patio area with outdoor seating, potted plants, and a view of the landscape.

14. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (73 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is CA $140
CA $193 total
includes taxes & fees
Nov 4 - Nov 5
Affitacamere Maria Gabriella
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

15. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.6 out of 10, Exceptional, (21 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is CA $156
CA $184 total
includes taxes & fees
Nov 9 - Nov 10
Corte Francigena - Apartments
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 CA $181
CA $206 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $633
CA $702 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

18. Dimora Santa Margherita - Boutique Hotel

Dimora Santa Margherita - Boutique Hotel
Cinigiano
8.2 out of 10, Very good, (12 reviews)
"We had a great time at this place. The room was spectacular and the views were some of the best on this entire trip. We would definitely come back. The only thing that we didn’t love was the menu at the restaurant is quite limited and there were not many things on the menu that appealed to us, as we were looking for more traditional Tuscan food. Breakfast was great and very traditional. The staff was fantastic and very helpful. Loved it."
Canada
Nicole
The price is CA $427
CA $473 total
includes taxes & fees
Oct 23 - Oct 24
Dimora Santa Margherita - Boutique Hotel
A stone archway leading to a dining area with a table set for two, overlooking a lush green landscape.

19. Agriturismo Poggio Monte

Agriturismo Poggio Monte
Manciano
9.8 out of 10, Exceptional, (14 reviews)
"A special place—quiet, clean, and cozy. Best of all, are the amazing people in charge of the place, who were very attentive and always made sure that everything ran smoothly."
United States
jason
The price is CA $138
CA $157 total
includes taxes & fees
Oct 25 - Oct 26
Agriturismo Poggio Monte
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

20. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is CA $124
CA $149 total
includes taxes & fees
Oct 29 - Oct 30
Idolina Guest House
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

Relais Cloister Pienza

Relais Cloister Pienza

10/10 Excellent
"An Incredible Terrace with the Most Amazing Views! ⭐⭐⭐⭐⭐ The hotel is beautifully restored and in a fantastic location in Pienza, just off Piazza Pio II. Our room was spotlessly clean, comfortable, with good bedding and a lovely large bathroom. The room itself was simple but very comfortable and had everything we needed. However, the absolute highlight of this hotel is the terrace. The views across the Val d’Orcia are quite simply out of this world! You could sit there for hours just taking it all in. We honestly think it must be the best spot in the whole of Pienza to enjoy those incredible Tuscan views. The staff were attentive and welcoming, and breakfast was also good. We would highly recommend staying here, especially for the terrace. If you want to experience the beauty of Tuscany from a truly breathtaking viewpoint, this is the place to stay!"
Jane 1-night trip
Posted 6 hours ago
Relais Cloister Pienza

Find out more about Piancastagnaio

Everything you need to know about Piancastagnaio vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Piancastagnaio vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Piancastagnaio vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Piancastagnaio vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Piancastagnaio. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Piancastagnaio vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Piancastagnaio vacation rentals we have selected for you start as low as CA $88 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Piancastagnaio rentals

At Expedia, we put the best Piancastagnaio vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Piancastagnaio rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Piancastagnaio vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Piancastagnaio. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best vacation home rentals that Piancastagnaio has to offer?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental near Piancastagnaio is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.