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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

Our top choices for Castiglione del Bosco holiday rentals

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 2.924.679 ₫
3.338.526 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Il Pozzo di Sant'Andrea
Double Room (Ginevra) | View from room

A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
8.0 out of 10, Very good, (28 reviews)
"Pleasant place"
France
Claude
The price is 3.627.807 ₫
4.111.967 ₫ total
includes taxes & fees
15 Jun - 16 Jun
A Casa Mastacchi
Suite, Multiple Beds, Valley View | Bathroom | Shower, rainfall showerhead, designer toiletries, hair dryer

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (144 reviews)
"Great location."
United States
James
The price is 3.641.365 ₫
4.126.881 ₫ total
includes taxes & fees
28 Jun - 29 Jun
La Locanda di San Francesco
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.6 out of 10, Exceptional, (204 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is 2.776.879 ₫
3.175.946 ₫ total
includes taxes & fees
3 Jul - 4 Jul
B&B Il Corso
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (67 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is 3.653.269 ₫
4.262.591 ₫ total
includes taxes & fees
21 Jun - 22 Jun
Villa Curina Resort
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (106 reviews)
"Place is amazing and maintained perfectly."
United States
Dominic
The price is 4.324.121 ₫
4.877.912 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Meublé Il Riccio
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.011.669 ₫
2.607.317 ₫ total
includes taxes & fees
17 Jun - 18 Jun
Tuscasì Aparthotel
Exterior

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (93 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is 3.917.198 ₫
4.430.327 ₫ total
includes taxes & fees
24 Jun - 25 Jun
B&B Le Scalette di Piazza
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, (90 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is 5.043.070 ₫
5.669.526 ₫ total
includes taxes & fees
16 Jun - 17 Jun
Casanova - Panoramic Rooms and Suites
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (172 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is 3.049.936 ₫
3.598.925 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Bosco della Spina
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 5.589.701 ₫
6.240.169 ₫ total
includes taxes & fees
16 Jun - 17 Jun
Abbadia Sicille Relais
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (37 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is 4.674.887 ₫
5.264.372 ₫ total
includes taxes & fees
13 Jun - 14 Jun
Delcorto Suites
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (146 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.453.591 ₫
6.181.916 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Hotel San Gregorio
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (91 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is 2.044.130 ₫
2.369.922 ₫ total
includes taxes & fees
3 Jul - 4 Jul
Domus il Palio B&B
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 2.122.750 ₫
2.486.749 ₫ total
includes taxes & fees
24 Jun - 25 Jun
RESIDENCE LECCIO
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (137 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is 3.568.841 ₫
4.047.074 ₫ total
includes taxes & fees
18 Jun - 19 Jun
Bed & Breakfast Vicolo dell'Oste
Seasonal outdoor pool, an infinity pool, free pool cabanas

Dimora Santa Margherita - Relais di Charme

Dimora Santa Margherita - Relais di Charme
Cinigiano
8.0 out of 10, Very good, (10 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 9.450.170 ₫
10.455.876 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Dimora Santa Margherita - Relais di Charme
Exterior

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is 2.740.954 ₫
3.075.738 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Country House il Ciliegio
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (339 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 2.322.221 ₫
2.676.440 ₫ total
includes taxes & fees
13 Jul - 14 Jul
ApartHotel Anghel
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is 2.270.315 ₫
2.618.726 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Residenza Fabroni
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

Piccolo Hotel Etruria

Piccolo Hotel Etruria

2/10 Terrible
"Air conditioning did not work. First, it won’t work if the key fob isn’t in (no electricity without the key in the wall) and it won’t work if a window is opened. So we turned it on and tried to sleep but it was so hot in the room we gave up. So we opened the windows. But people on the streets of Siena are loud. So didn’t get to sleep until 4. At 7, it was so loud again that we couldn’t sleep. So we reported the problem. Was told that opening the windows was a good solution. The air conditioner was clearly not serviced in years and couldn’t get air in due to clogged filters. So two sleepless nights."
Renato 2-night trip
Posted 6 hours ago
Piccolo Hotel Etruria

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.