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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Castiglione del Bosco holiday rentals

Standard Double Room (La Piazza)

1. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (99 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is NZ$261
includes taxes & fees
4 Aug - 5 Aug
B&B Le Scalette di Piazza
Breakfast, lunch and dinner served

2. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! The staff are exceptional- so helpful and kind with every aspect of the stay. The rooms are beautiful and lovely amenities upon arrival. Would definitely go back again!"
United States
Victoria
The price is NZ$495
includes taxes & fees
1 Aug - 2 Aug
Palazzo Saloni
Exterior

3. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"This is a wonderful B&B that is part of the historic district. Sloping uneven floors, which is the charm of having the chance to stay in a piece of history. A very comfortable room, with breakfast at a cafe nearby. Parking option is nearby, just talk with your host who is so helpful. Wonderful location to walk and enjoy all the town has to offer."
United States
Sophie
The price is NZ$212
includes taxes & fees
18 Aug - 19 Aug
Idolina Guest House
Exterior

4. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"was such a beautiful location I dont have anything bad to say about it...would definitely go again for a relaxing and tranquil stay - you definitely need a car to get there though and to go around.."
United States
Hanna
The price is NZ$328
includes taxes & fees
30 Aug - 31 Aug
Corte Francigena - Apartments
Aerial view

5. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (175 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 NZ$315
includes taxes & fees
31 Aug - 1 Sept
Bosco della Spina
1 treatment room, massages

6. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (92 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is NZ$346
includes taxes & fees
31 Aug - 1 Sept
Casanova - Panoramic Rooms and Suites
Front of property

7. 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 NZ$177
includes taxes & fees
1 Aug - 2 Aug
RESIDENCE LECCIO
Pool

8. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is NZ$665
includes taxes & fees
2 Aug - 3 Aug
Agritourism in val d'orcia
Outdoor dining

9. Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is NZ$274
includes taxes & fees
2 Aug - 3 Aug
Podere Belsogno-camera Lavanda
Exterior

10. FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA

FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA
Buonconvento
10.0 out of 10, Exceptional, (37 reviews)
"This place is amazing! The hosts are so sweet and accommodated our crazy schedule with missing trains/traffic and checking in later. Such a gem of a place. The property is amazing"
United States
Hannah S.
The price is NZ$606
includes taxes & fees
4 Aug - 5 Aug
FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA
Couples treatment room(s), sauna, hot tub, steam room, body treatments

11. 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, (49 reviews)
"Our stay was great. "
United States
Elena
The price is NZ$195
includes taxes & fees
2 Aug - 3 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Exterior detail

12. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (9 reviews)
"Loved it!"
United States
Ryan C.
The price is NZ$351
includes taxes & fees
28 Aug - 29 Aug
Exclusive Stone Tower.
Interior

13. Apartment 'Casa Francesca' with Hills View & Courtyard

Apartment 'Casa Francesca' with Hills View & Courtyard
Montalcino
10.0 out of 10, Exceptional, (3 reviews)
"Clean property and amazing view. Great location "
United States
Angela B.
The price is NZ$821
includes taxes & fees
31 Aug - 1 Sept
Apartment 'Casa Francesca' with Hills View & Courtyard
Premium bedding, down duvets, pillow-top beds, desk

14. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$176
includes taxes & fees
5 Aug - 6 Aug
Tuscasì Aparthotel
Interior

15. Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Montalcino
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa."
United States
Robert K.
The price is NZ$1,651
includes taxes & fees
2 Aug - 3 Aug
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Seasonal outdoor pool

16. Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
10.0 out of 10, Exceptional, (2 reviews)
"Location was perfect, restaurants were excellent, views spectacular. Will highly recommend!"
United States
David
The price is NZ$543
includes taxes & fees
31 Aug - 1 Sept
Albergo Diffuso Borgo Santo
Food and drink

17. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is NZ$443
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Terrace/patio

18. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is NZ$372
includes taxes & fees
31 Aug - 1 Sept
Abbadia Sicille Relais
Suite, 2 Bedrooms | Courtyard view

19. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is NZ$870
includes taxes & fees
3 Aug - 4 Aug
L'Olmo
Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

20. Podere Vesta

Podere Vesta
3.0 star property
Asciano
9.2 out of 10, Wonderful, (20 reviews)
"This was the best stay and experience during our 20 days trip to italy. Beautiful property 20min from Siena. It had everything we needed. The apartment is stocked with everything you could need for a long stay. My son had so much fun, and the free bikes were a plus. Make sure to pass by a grocery store before arriving, you won’t want to leave the property"
United States
Katerine
The price is NZ$357
includes taxes & fees
30 Aug - 31 Aug
Podere Vesta
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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"Loved our stay at the property. Extremely friendly and attentive staff, beautifully clean rooms, delicious breakfast and a great pool area."
Frederick 4-night trip
Posted 1 day ago
Villa Scacciapensieri Boutique Hotel

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$160 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?

Idyllic guest house in Tuscan country house style with swimming pool: This holiday home rental outside of Castiglione del Bosco is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a patio and a garden.

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 Val di Merse. 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.