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 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Castiglione del Bosco vacation rentals

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 NT$6,127
NT$6,888 total
includes taxes & fees
Apr 23 - Apr 24
Casanova - Panoramic Rooms and Suites
Panoramic Cottage, 1 Bedroom | Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (53 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 NT$3,592
NT$4,874 total
includes taxes & fees
Apr 17 - Apr 18
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 NT$3,188
NT$3,655 total
includes taxes & fees
Apr 14 - Apr 15
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 NT$3,547
NT$4,012 total
includes taxes & fees
Apr 19 - Apr 20
Abbadia Sicille Relais
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is NT$2,334
NT$2,568 total
includes taxes & fees
Apr 22 - Apr 23
La Dimora di Dida
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is NT$4,358
NT$4,942 total
includes taxes & fees
Apr 16 - Apr 17
Bed & Breakfast Vicolo dell'Oste
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 NT$3,577
NT$4,083 total
includes taxes & fees
Apr 14 - Apr 15
B&B Le Scalette di Piazza
Seasonal outdoor pool, an infinity pool, free cabanas, pool umbrellas

Dimora Santa Margherita - Relais di Charme

Dimora Santa Margherita - Relais di Charme
Cinigiano
7.8 out of 10, Good, (9 reviews)
"The place was great! Food from their was amazing but also a bit expensive. Poolarea was so beautiful and the view was amazing! Only negative thing is that the wine tasting is not in hotel, need to take own car drive for that. Also the last 2km was sand road, which was not that good shape."
Finland
Anonymous traveler
The price is NT$12,105
NT$13,390 total
includes taxes & fees
May 11 - May 12
Dimora Santa Margherita - Relais di Charme
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is NT$7,455
NT$8,312 total
includes taxes & fees
Apr 14 - Apr 15
Luxury resort in the Tuscan countryside
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (98 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is NT$2,614
NT$3,023 total
includes taxes & fees
Apr 12 - Apr 13
Residenza Fabroni
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 NT$5,672
NT$6,388 total
includes taxes & fees
Apr 11 - Apr 12
Delcorto Suites
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 NT$2,661
NT$3,039 total
includes taxes & fees
Apr 12 - Apr 13
Casa di Campagna in Toscana
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 NT$11,486
NT$12,931 total
includes taxes & fees
Apr 13 - Apr 14
Borgo Lucignanello Bandini
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (22 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is NT$14,884
NT$16,521 total
includes taxes & fees
Apr 15 - Apr 16
L'Olmo
Front of property

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is NT$5,684
NT$6,549 total
includes taxes & fees
Apr 22 - Apr 23
Villa Curina Resort
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (430 reviews)
"Nice place!"
United States
Pavel
The price is NT$3,315
NT$3,795 total
includes taxes & fees
Apr 12 - Apr 13
Siena Vip
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (198 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is NT$3,766
NT$4,292 total
includes taxes & fees
Apr 12 - Apr 13
B&B Il Corso
Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is NT$7,336
NT$8,255 total
includes taxes & fees
Apr 11 - Apr 12
Albergo Diffuso Borgo Santo
Property grounds

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Great time, perfect property and location."
United States
Christopher
The price is NT$7,072
NT$7,927 total
includes taxes & fees
Apr 12 - Apr 13
Ca' Bianca Tuscany Relais
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (140 reviews)
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
United States
beverly
The price is NT$6,684
NT$7,575 total
includes taxes & fees
Apr 17 - Apr 18
Hotel San Gregorio
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
"Excellent location. Less than 15 minute walk to major attractions. Numerous restaurants close by. "
Kathleen 2-night trip
Posted 18 hours 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’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.