A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.

Castiglione del Bosco 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 Castiglione del Bosco vacation rentals

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

1. 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 ￥14,526
￥17,400 total
includes taxes & fees
Nov 14 - Nov 15
Idolina Guest House
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

2. 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 ￥18,902
￥21,504 total
includes taxes & fees
Nov 8 - Nov 9
B&B Le Scalette di Piazza
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

3. 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 ￥44,503
￥50,730 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Saloni
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

4. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (185 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is ￥14,056
￥16,884 total
includes taxes & fees
Oct 26 - Oct 27
Bosco della Spina
A poolside area with two glasses of water, candles, and a stone pathway.

5. 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 ￥27,013
￥30,425 total
includes taxes & fees
Oct 21 - Oct 22
Casanova - Panoramic Rooms and Suites
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

6. 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 ￥17,499
￥20,671 total
includes taxes & fees
Nov 1 - Nov 2
Corte Francigena - Apartments
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

7. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥9,860
￥13,157 total
includes taxes & fees
Nov 4 - Nov 5
Tuscasì Aparthotel
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

8. 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 ￥20,356
￥23,102 total
includes taxes & fees
Nov 9 - Nov 10
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

9. 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 ￥20,154
￥23,235 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
A historic building with a tower, a courtyard, and a well-lit entrance.

10. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is ￥11,778
￥13,489 total
includes taxes & fees
Oct 21 - Oct 22
Abbadia Sicille Relais
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

11. Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is ￥21,327
￥24,881 total
includes taxes & fees
Oct 21 - Oct 22
Podere Belsogno-camera Lavanda
A villa with a swimming pool, outdoor seating, and a tennis court.

12. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is ￥23,218
￥26,251 total
includes taxes & fees
Oct 21 - Oct 22
Villa Curina Resort
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

13. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is ￥14,236
￥24,899 total
includes taxes & fees
Oct 21 - Oct 22
Exclusive Stone Tower.
A stone building with a courtyard, outdoor seating, and a warm light setting.

14. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is ￥15,850
￥19,568 total
includes taxes & fees
Nov 4 - Nov 5
Sarna Residence
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, (73 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ￥17,230
￥23,378 total
includes taxes & fees
Oct 28 - Oct 29
Affitacamere Maria Gabriella
A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

16. Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful stay "
United States
Marc
The price is ￥54,152
￥61,344 total
includes taxes & fees
Nov 8 - Nov 9
Borgo Lucignanello Bandini
A stone building with a sign reading "Borgo di Mezzo".

17. The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (15 reviews)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is ￥17,772
￥25,236 total
includes taxes & fees
Oct 21 - Oct 22
The Gelda house, relax with a view
A stone building with a wooden door and two windows with shutters.

18. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (23 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is ￥26,658
￥36,255 total
includes taxes & fees
Nov 3 - Nov 4
The Casetta di Brunello, quiet and breathtaking views
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

19. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is ￥13,087
￥15,284 total
includes taxes & fees
Oct 21 - Oct 22
RESIDENCE LECCIO
A person in a swimming pool with a view of trees and distant hills.

20. Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
10.0 out of 10, Exceptional, (3 reviews)
"Location was perfect, restaurants were excellent, views spectacular. Will highly recommend!"
United States
David
The price is ￥33,234
￥37,446 total
includes taxes & fees
Nov 19 - Nov 20
Albergo Diffuso Borgo Santo
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 Castiglione del Bosco Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good
"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."
Marcela 3-night trip
Posted 8 hours ago
Villa Ermellina Siena, a Tribute Portfolio Hotel

Find out more about Castiglione del Bosco

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

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Frequently asked questions

Can I find vacation rentals in Castiglione del Bosco?

Yes, there are vacation rentals close to well known attractions in Castiglione del Bosco, or you can choose a more secluded option if you want a relaxing place to stay. Castiglione del Bosco is known for its restaurants.

What are some of the best vacation home rentals in Castiglione del Bosco?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home rental near Castiglione del Bosco is located in the city center and has a fireplace, a balcony, 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 terrace, a garden, and a selection of books so you can immerse yourself in your vacation.

What’s there to see and do in Castiglione del Bosco?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like Horti Leonini. Castiglion del Bosco Winery and Fortress of Montalcino are a couple of places you'll find in the larger area.

What’s a vacation rental in Castiglione del Bosco like?

A vacation rental is a private property where you can stay for short or long periods in Castiglione del Bosco. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip.