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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Castiglione del Bosco vacation rentals

Superior Penthouse, City View | Desk, laptop workspace, soundproofing, iron/ironing board

1. The Altana- Siena Views

The Altana- Siena Views
Siena City Centre
The price is ￥67,958
￥75,676 total
includes taxes & fees
Sep 13 - Sep 14
The Altana- Siena Views
Comfort Studio, Hill View | Soundproofing, iron/ironing board, WiFi (free)

2. Belvedere Nada

Belvedere Nada
San Rocco A Pilli
The price is ￥31,932
￥35,126 total
includes taxes & fees
Sep 9 - Sep 10
Belvedere Nada
Standard Double Room (La Piazza) | Desk, soundproofing, WiFi (free), bed sheets

3. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (100 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is ￥20,372
￥23,147 total
includes taxes & fees
Aug 23 - Aug 24
B&B Le Scalette di Piazza
Front of property

4. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is ￥17,235
￥20,434 total
includes taxes & fees
Aug 31 - Sep 1
Idolina Guest House
Aerial view

5. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (176 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 ￥24,867
￥28,831 total
includes taxes & fees
Sep 14 - Sep 15
Bosco della Spina
Premium bedding, down comforters, pillowtop beds, desk

6. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥12,034
￥15,637 total
includes taxes & fees
Aug 21 - Aug 22
Tuscasì Aparthotel
Double Room (Ginevra) | View from room

7. A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
7.8 out of 10, Good, (29 reviews)
"Christiana was the perfect hostess. Accommodations were quaint. Rooms and common areas were spotless. Breakfast and cafe were amazing. A true gem located in the heart of Siena. Close to shops, restaurants, and enotecas. I highly recommend you stay. "
United States
Christina
The price is ￥20,488
￥23,275 total
includes taxes & fees
Aug 19 - Aug 20
A Casa Mastacchi
Couples treatment rooms, sauna, hot tub, steam room, body treatments

8. 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 ￥28,190
￥31,747 total
includes taxes & fees
Aug 21 - Aug 22
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
1 treatment room, massages

9. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is ￥27,458
￥30,941 total
includes taxes & fees
Sep 1 - Sep 2
Casanova - Panoramic Rooms and Suites
Food and drink

10. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (154 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ￥35,203
￥39,830 total
includes taxes & fees
Aug 25 - Aug 26
Hotel San Gregorio
Terrace/patio

11. 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 ￥27,751
￥31,080 total
includes taxes & fees
Aug 19 - Aug 20
Abbadia Sicille Relais
Aerial view

12. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is ￥28,694
￥32,302 total
includes taxes & fees
Aug 19 - Aug 20
Villa Curina Resort
Breakfast, lunch and dinner served

13. 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 ￥56,106
￥63,194 total
includes taxes & fees
Aug 20 - Aug 21
Palazzo Saloni
Breakfast meal

14. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (205 reviews)
"Lovely B&B right in the heart of Siena. Pierre was incredibly helpful and kept me up to date prior to my arrival with suggestions for dining out, shopping and bars. Would highly recommend"
United Kingdom
Katherine
The price is ￥18,684
￥21,290 total
includes taxes & fees
Aug 21 - Aug 22
B&B Il Corso
Room amenity

15. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (474 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is ￥20,112
￥22,860 total
includes taxes & fees
Aug 23 - Aug 24
Siena Vip
Exterior

16. 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 ￥26,399
￥30,885 total
includes taxes & fees
Aug 30 - Aug 31
Corte Francigena - Apartments
Interior

17. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is ￥25,777
￥29,093 total
includes taxes & fees
Aug 22 - Aug 23
Meublé Il Riccio
Exterior

18. 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 ￥18,403
￥20,981 total
includes taxes & fees
Sep 3 - Sep 4
Il Pozzo di Sant'Andrea
Suite Aria | Terrace/patio

19. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 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 ￥28,135
￥31,686 total
includes taxes & fees
Aug 20 - Aug 21
Delcorto Suites
Property entrance

20. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 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 ￥14,123
￥16,273 total
includes taxes & fees
Aug 21 - Aug 22
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Tyler 1-night trip
Posted 1 hour ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Castiglione del Bosco

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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 Val di Merse. 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.