A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.

Castiglione del Bosco Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Castiglione del Bosco holiday rentals

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

1. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is NZ$188
includes taxes & fees
25 Nov - 26 Nov
Idolina Guest House
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

2. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (188 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is NZ$191
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

3. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"We had a great stay in this conveniently located property. The breakfast was good with many options and staff to assist."
Canada
Morris
The price is NZ$240
includes taxes & fees
8 Nov - 9 Nov
B&B Le Scalette di Piazza
A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

4. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is NZ$513
includes taxes & fees
30 Nov - 1 Dec
Palazzo Saloni
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

5. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is NZ$241
includes taxes & fees
1 Nov - 2 Nov
Corte Francigena - Apartments
A pool area with lounge chairs and umbrellas, surrounded by tall cypress trees and a view of distant hills.

6. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (104 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is NZ$358
includes taxes & fees
24 Nov - 25 Nov
Casanova - Panoramic Rooms and Suites
A stone building with a courtyard, outdoor seating, and a warm light setting.

7. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is NZ$228
includes taxes & fees
8 Nov - 9 Nov
Sarna Residence
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

8. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (168 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is NZ$280
includes taxes & fees
5 Nov - 6 Nov
Hotel San Gregorio
A stone-walled room with a fireplace, a hot tub, candles, and a tray with snacks.

9. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is NZ$233
includes taxes & fees
19 Nov - 20 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A villa with a swimming pool, outdoor seating, and a tennis court.

10. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (83 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is NZ$264
includes taxes & fees
31 Oct - 1 Nov
Villa Curina Resort
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

11. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$135
includes taxes & fees
30 Nov - 1 Dec
Tuscasì Aparthotel
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

12. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is NZ$133
includes taxes & fees
26 Nov - 27 Nov
Abbadia Sicille Relais
A patio area with outdoor seating, potted plants, and a view of the landscape.

13. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is NZ$236
includes taxes & fees
30 Nov - 1 Dec
Affitacamere Maria Gabriella
An aerial view of a historic castle complex with multiple buildings, including a large central structure with a tower, surrounded by well-maintained gardens and pathways.

14. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is NZ$360
includes taxes & fees
31 Oct - 1 Nov
Castello di Modanella
A person in a swimming pool with a view of trees and distant hills.

15. Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
10.0 out of 10, Exceptional, (3 reviews)
"Location was perfect, restaurants were excellent, views spectacular. Will highly recommend!"
United States
David
The price is NZ$399
includes taxes & fees
2 Nov - 3 Nov
Albergo Diffuso Borgo Santo
A stone courtyard with a bench, potted plants, and a building in the background.

16. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is NZ$168
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
A stone-paved courtyard with a wrought iron gate, a brick building, and a tree.

17. B&B Le Logge Di Sopra

B&B Le Logge Di Sopra
Asciano
The price is NZ$209
includes taxes & fees
24 Nov - 25 Nov
B&B Le Logge Di Sopra
A white table with a bowl of snacks, two glasses of orange drink, and a small potted plant on a balcony.

18. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is NZ$140
includes taxes & fees
12 Nov - 13 Nov
RESIDENCE LECCIO
A hotel room with a bed, a chair, a lamp, and a view of the outdoors.

19. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is NZ$296
includes taxes & fees
26 Nov - 27 Nov
La Locanda di San Francesco
Exterior

20. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is NZ$231
includes taxes & fees
31 Oct - 1 Nov
montorio
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

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 13 hours ago
Hotel Athena

Find out more about Castiglione del Bosco

Everything you need to know about Castiglione del Bosco holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglione del Bosco holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglione del Bosco holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Castiglione del Bosco holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglione del Bosco. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castiglione del Bosco holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castiglione del Bosco holiday rentals we have selected for you start as low as NZ$114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castiglione del Bosco rentals

At Expedia, we put the best Castiglione del Bosco holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Castiglione del Bosco rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglione del Bosco holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglione del Bosco. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 are some of the best holiday rentals that Castiglione del Bosco has to offer?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This holiday home rental outside of Castiglione del Bosco is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of books so that you can immerse yourself in your holiday.

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.