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

Castiglione del Bosco Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Castiglione del Bosco vacation rentals

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

1. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (103 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is AED 438
AED 499 total
includes taxes & fees
13 Oct - 14 Oct
B&B Le Scalette di Piazza
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, (179 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 AED 296
AED 359 total
includes taxes & fees
27 Oct - 28 Oct
Bosco della Spina
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

3. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is AED 315
AED 380 total
includes taxes & fees
27 Oct - 28 Oct
Idolina Guest House
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

4. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is AED 801
AED 922 total
includes taxes & fees
6 Nov - 7 Nov
Palazzo Saloni
A poolside area with two glasses of water, candles, and a stone pathway.

5. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (99 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is AED 617
AED 695 total
includes taxes & fees
30 Oct - 31 Oct
Casanova - Panoramic Rooms and Suites
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

6. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is AED 421
AED 496 total
includes taxes & fees
2 Nov - 3 Nov
Corte Francigena - Apartments
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.

7. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AED 229
AED 305 total
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

8. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (159 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is AED 478
AED 551 total
includes taxes & fees
6 Nov - 7 Nov
Hotel San Gregorio
A villa with a swimming pool, outdoor seating, and a tennis court.

9. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is AED 426
AED 485 total
includes taxes & fees
12 Oct - 13 Oct
Villa Curina Resort
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

10. 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 AED 446
AED 507 total
includes taxes & fees
2 Nov - 3 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

11. 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 AED 495
AED 577 total
includes taxes & fees
7 Oct - 8 Oct
Podere Belsogno-camera Lavanda
A stone building with a courtyard, outdoor seating, and a warm light setting.

12. 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 AED 384
AED 472 total
includes taxes & fees
3 Nov - 4 Nov
Sarna Residence
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

13. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is AED 330
AED 577 total
includes taxes & fees
7 Oct - 8 Oct
Exclusive Stone Tower.
A patio area with outdoor seating, potted plants, and a view of the landscape.

14. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (69 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is AED 376
AED 516 total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

15. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (26 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is AED 1,649
AED 1,830 total
includes taxes & fees
2 Nov - 3 Nov
L'Olmo
A narrow stone alley with potted plants and benches.

16. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (77 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 618
AED 841 total
includes taxes & fees
1 Nov - 2 Nov
The House of Alice, charm and relaxation
A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

17. Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful stay "
United States
Marc
The price is AED 1,179
AED 1,339 total
includes taxes & fees
13 Oct - 14 Oct
Borgo Lucignanello Bandini
A historic building with a tower, a courtyard, and a well-lit entrance.

18. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is AED 384
AED 435 total
includes taxes & fees
5 Nov - 6 Nov
Abbadia Sicille Relais
Outdoor pool

19. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is AED 529
AED 594 total
includes taxes & fees
8 Oct - 9 Oct
Residence Arianna
A stone building with a wooden door and two windows with shutters.

20. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is AED 618
AED 841 total
includes taxes & fees
3 Nov - 4 Nov
The Casetta di Brunello, quiet and breathtaking views
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 9 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

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?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home rental near Castiglione del Bosco is located in the city center and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation.

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 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.