Search Holiday Rentals in Castiglione del Bosco

  • 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
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Castiglione del Bosco holiday 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 ฿6,232
฿7,006 total
includes taxes & fees
10 May - 11 May
Casanova - Panoramic Rooms and Suites
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (171 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿4,163
฿4,692 total
includes taxes & fees
19 Apr - 20 Apr
Abbadia Sicille Relais
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 ฿3,654
฿4,958 total
includes taxes & fees
17 Apr - 18 Apr
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 ฿3,229
฿3,702 total
includes taxes & fees
16 Apr - 17 Apr
Il Pozzo di Sant'Andrea
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is ฿2,374
฿2,612 total
includes taxes & fees
15 Apr - 16 Apr
La Dimora di Dida
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 ฿2,649
฿3,065 total
includes taxes & fees
19 Apr - 20 Apr
Residenza Fabroni
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 ฿3,638
฿4,153 total
includes taxes & fees
3 May - 4 May
B&B Le Scalette di Piazza
Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is ฿7,462
฿8,397 total
includes taxes & fees
15 Apr - 16 Apr
Albergo Diffuso Borgo Santo
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 ฿3,357
฿3,843 total
includes taxes & fees
15 Apr - 16 Apr
Bed & Breakfast Vicolo dell'Oste
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 ฿6,333
฿7,192 total
includes taxes & fees
7 May - 8 May
Hotel San Gregorio
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 ฿7,590
฿8,499 total
includes taxes & fees
15 Apr - 16 Apr
Ca' Bianca Tuscany Relais
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 ฿5,352
฿6,037 total
includes taxes & fees
15 Apr - 16 Apr
Meublé Il Riccio
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 ฿3,815
฿4,347 total
includes taxes & fees
29 Apr - 30 Apr
B&B Il Corso
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is ฿7,557
฿8,425 total
includes taxes & fees
20 Apr - 21 Apr
Luxury resort in the Tuscan countryside
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 ฿5,745
฿6,470 total
includes taxes & fees
15 Apr - 16 Apr
Delcorto Suites
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (23 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ฿15,023
฿16,676 total
includes taxes & fees
19 Apr - 20 Apr
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 ฿5,761
฿6,638 total
includes taxes & fees
24 Apr - 25 Apr
Villa Curina Resort
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 ฿11,643
฿13,183 total
includes taxes & fees
22 Apr - 23 Apr
Borgo Lucignanello Bandini
Exterior

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"Excellent service, ideal location"
United Kingdom
Nigel
The price is ฿2,522
฿3,075 total
includes taxes & fees
16 Apr - 17 Apr
Idolina Guest House
Seasonal outdoor pool, an infinity pool, free pool cabanas

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 traveller
The price is ฿7,140
฿7,930 total
includes taxes & fees
27 Apr - 28 Apr
Dimora Santa Margherita - Relais di Charme
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"It was an amazing experience staying here "
Hilario 3-night trip
Posted 1 hour ago
Grand Hotel Continental Siena – Starhotels Collezione

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 holiday rentals in Castiglione del Bosco?

Yes, there are holiday rentals close to the most popular sights in Castiglione del Bosco, or you can select a more secluded option if you're looking for a relaxing 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 wider area.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castiglione del Bosco. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.