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Castiglione del Bosco Vacation Rentals

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Check prices for these dates

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Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Castiglione del Bosco vacation rentals

View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥11,847
￥13,582 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Abbadia Sicille Relais
Birthday party area
Siena Vip

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (423)
"A great location!"
Canada
Cheryl
The price is ￥21,902
￥24,826 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siena Vip
Royal Apartment | View from room
Tuscasì Aparthotel

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥10,660
￥14,113 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Tuscasì Aparthotel
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Exterior
Meublé Il Riccio

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"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
Affitacamere Maria Gabriella
Exterior
La Dimora di Dida

Residence in Seggiano

La Dimora di Dida
The price is ￥11,392
￥12,531 total
includes taxes & fees
Jan 8 - Jan 9, 2026
La Dimora di Dida
Camera Superior, vista città, primo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi
TuscanyLettings Studio&Room

Townhouse in Pienza

TuscanyLettings Studio&Room
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is ￥14,695
￥16,899 total
includes taxes & fees
Jan 9 - Jan 10, 2026
TuscanyLettings Studio&Room
Seasonal outdoor pool
Albergo Diffuso Borgo Santo

Aparthotel in Asciano

Albergo Diffuso Borgo Santo
The price is ￥40,413
￥45,372 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Albergo Diffuso Borgo Santo
Seasonal outdoor pool, pool umbrellas, sun loungers
Country House il Ciliegio

Apartment in Roccastrada

Country House il Ciliegio
9.2 out of 10, Wonderful, (7)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is ￥10,937
￥12,031 total
includes taxes & fees
Jan 30 - Jan 31, 2026
Country House il Ciliegio
Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ￥13,098
￥15,143 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PienzaLettings Suites
Free WiFi
Affittacamere Mariuccia

Townhouse in Montalcino

Affittacamere Mariuccia
9.0 out of 10, Wonderful, (11)
"The apartment was big enough, the owner very polite and helpful. But, there were bugs at our mattress... "
United Kingdom
Angeliki
Affittacamere Mariuccia
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very Good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ￥10,262
￥12,022 total
includes taxes & fees
Jan 22 - Jan 23, 2026
ApartHotel Anghel
Quadruple Room, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Townhouse in Siena City Centre

Al Mercato B&B
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is ￥11,857
￥15,394 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Al Mercato B&B
Terrace/patio
Casa di Campagna in Toscana

Townhouse in Sovicille

Casa di Campagna in Toscana
9.4 out of 10, Exceptional, (20)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana
Daily cooked-to-order breakfast (EUR 15 per person)
La Coroncina Lodging

Aparthotel in Siena

La Coroncina Lodging
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ￥15,738
￥18,046 total
includes taxes & fees
Jan 8 - Jan 9, 2026
La Coroncina Lodging
Exterior
Villa le Camelie Siena

Townhouse in Petriccio

Villa le Camelie Siena
8.6 out of 10, Excellent, (8)
"Personal people are very good. "
Switzerland
Wenjuan
The price is ￥15,022
￥17,258 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Villa le Camelie Siena
Double Room (Ginevra) | View from room
A Casa Mastacchi

Townhouse in Siena City Centre

A Casa Mastacchi
7.8 out of 10, Good, (25)
"Pleasant place"
France
Claude
The price is ￥15,113
￥17,359 total
includes taxes & fees
Jan 8 - Jan 9, 2026
A Casa Mastacchi
Front of property - evening/night
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Restaurant
B&B Dei Rossi

Townhouse in Siena City Centre

B&B Dei Rossi
8.2 out of 10, Very Good, (18)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
The price is ￥11,925
￥13,852 total
includes taxes & fees
Jan 30 - Jan 31, 2026
B&B Dei Rossi
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

Hotel Athena

Hotel Athena

10/10 Excellent
"Staff"
Young 3-night trip
Posted 2 days ago
Hotel Athena

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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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?

The House of Alice, charm and relaxation: This vacation home rental near Castiglione del Bosco is located in a rural location and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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 Historic Centre of Pienza. 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.