Castiglione del Bosco Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Castiglione del Bosco vacation rentals

Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is ￥11,582
￥12,740 total
includes taxes & fees
Apr 14 - Apr 15
La Dimora di Dida
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (79 reviews)
"Fantastic place"
United States
Clifford
The price is ￥27,475
￥30,959 total
includes taxes & fees
Apr 14 - Apr 15
Casanova - Panoramic Rooms and Suites
Panoramic Cottage, 1 Bedroom | Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
The price is ￥16,934
￥23,204 total
includes taxes & fees
Apr 15 - Apr 16
Affitacamere Maria Gabriella
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ￥14,490
￥16,674 total
includes taxes & fees
Apr 11 - Apr 12
Il Pozzo di Sant'Andrea
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (170 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥17,820
￥20,154 total
includes taxes & fees
Apr 19 - Apr 20
Abbadia Sicille Relais
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (134 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is ￥28,745
￥32,354 total
includes taxes & fees
Apr 19 - Apr 20
La Locanda di San Francesco
Exterior

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (92 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is ￥15,930
￥18,258 total
includes taxes & fees
Apr 15 - Apr 16
B&B Le Scalette di Piazza
Balcony

Osteria del Borgo

Osteria del Borgo
Montepulciano
9.2 out of 10, Wonderful, (158 reviews)
"I had a wonderful stay at Osteria del Borgo. The property was exceptionally clean and perfectly located right in the center of town, making it easy to walk everywhere. Communication throughout was excellent—the staff were friendly, responsive, and genuinely welcoming. The breakfast was amazing, with a great selection and quality. A special thanks to the owner, who went above and beyond by helping with parking and being very flexible with check-in, which made the whole experience even...
United States
Florian
Osteria del Borgo
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥12,037
￥15,631 total
includes taxes & fees
Apr 9 - Apr 10
Tuscasì Aparthotel
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is ￥31,135
￥34,984 total
includes taxes & fees
Apr 9 - Apr 10
Delcorto Suites
Terrace/patio

Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is ￥50,225
￥56,720 total
includes taxes & fees
Apr 15 - Apr 16
Borgo Lucignanello Bandini
Exterior

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
The price is ￥17,689
￥20,193 total
includes taxes & fees
Apr 21 - Apr 22
Casa Gioia - Casa Olivieri
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is ￥16,087
￥18,247 total
includes taxes & fees
Apr 9 - Apr 10
Casa di Campagna in Toscana
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is ￥34,771
￥38,800 total
includes taxes & fees
Apr 7 - Apr 8
Luxury resort in the Tuscan countryside
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (197 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is ￥18,635
￥21,235 total
includes taxes & fees
Apr 8 - Apr 9
B&B Il Corso
Terrace/patio

Antico Brunello

Antico Brunello
Montalcino
The price is ￥1,213,353
￥1,336,526 total
includes taxes & fees
Apr 4 - Apr 5
Antico Brunello
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (91 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is ￥24,887
￥28,111 total
includes taxes & fees
Apr 10 - Apr 11
Meublé Il Riccio
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (129 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ￥15,568
￥17,860 total
includes taxes & fees
Apr 6 - Apr 7
Bed & Breakfast Vicolo dell'Oste
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (96 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ￥14,435
￥16,615 total
includes taxes & fees
Apr 16 - Apr 17
Residenza Fabroni
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (200 reviews)
"Room was excellent, location was perfect for seeing Siena and restaurant was also excellent"
United Kingdom
John
The price is ￥20,877
￥23,701 total
includes taxes & fees
Apr 16 - Apr 17
Il Battistero Siena - Residenza d'Epoca
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castiglione del Bosco Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"El jardín súper cómodo y a gusto para ver atardeceres "
Ingrid Gabriela 1-night trip
Posted 2 days ago
Palazzo Ravizza

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:

  • View our selection of featured holiday rentals in Castiglione del Bosco
  • Use the map to find apartments and other holiday homes in the Castiglione del Bosco neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castiglione del Bosco while they last

Look no further and take a look at our great range of rental properties in Castiglione del Bosco!

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?

Beautiful stone house with garden and private pool.: This vacation home rental near Castiglione del Bosco is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

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.