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5 Star Hotels in Castiglione del Bosco

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Tonight Apr 25 - Apr 26This weekend Apr 25 - Apr 27

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Featured 5 Star Castiglione del Bosco Hotels

Grand Hotel Continental Siena – Starhotels Collezione
5 out of 5
Fully refundableReserve now, pay when you stay
  • 41 min drive from Castiglion del Bosco Winery
The price is $421 per night from Apr 26 to Apr 27
$421
includes taxes & fees
Apr 26 - Apr 27
Stay at this 5-star luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the room service ...
Grand Hotel Continental Siena – Starhotels Collezione
Borgo Sant'Ambrogio Resort
5 out of 5
  • 29 min drive from Castiglion del Bosco Winery
The price is $263 per night from May 11 to May 12
$263
includes taxes & fees
May 11 - May 12
Stay at this 5-star luxury farm stay in Trequanda. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Borgo Sant'Ambrogio Resort
Borgo Santo Pietro
5 out of 5
  • 33 min drive from Castiglion del Bosco Winery
The price is $1,779 per night from May 14 to May 15
$1,779
includes taxes & fees
May 14 - May 15
Stay at this 5-star luxury hotel in Chiusdino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di San Galgano and Eremo di Montesiepi ...
Borgo Santo Pietro
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Rosewood Castiglion del Bosco
5 out of 5
Fully refundableReserve now, pay when you stay
  • 6 min walk from Castiglion del Bosco Winery
The price is $1,367 per night from Apr 26 to Apr 27
$1,367
includes taxes & fees
Apr 26 - Apr 27
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
Rosewood Castiglion del Bosco
Castello di Velona Resort Thermal SPA & Winery
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Castiglion del Bosco Winery
The price is $470 per night from Apr 27 to Apr 28
$470
includes taxes & fees
Apr 27 - Apr 28
Stay at this 5-star luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
Castello di Velona Resort Thermal SPA & Winery
Castello Banfi - Il Borgo
5 out of 5
  • 17 min drive from Castiglion del Bosco Winery
The price is $991 per night from Apr 29 to Apr 30
$991
includes taxes & fees
Apr 29 - Apr 30
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Castello Banfi and Poggio Antico are ...
Castello Banfi - Il Borgo
 La Bagnaia Golf Resort
5 out of 5
Fully refundableReserve now, pay when you stay
  • 27 min drive from Castiglion del Bosco Winery
The price is $255 per night from May 20 to May 21
$255
includes taxes & fees
May 20 - May 21
Stay at this 5-star luxury hotel in Murlo. Enjoy free WiFi, free parking, and an outdoor pool. Popular attraction Val di Merse is located nearby.
La Bagnaia Golf Resort
ADLER Spa Resort Thermae
5 out of 5
  • 23 min drive from Castiglion del Bosco Winery
The price is $868 per night from May 12 to May 13
$868
includes taxes & fees
May 12 - May 13
Stay at this 5-star luxury hotel in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Piazza delle Sorgenti and Tenuta ...
ADLER Spa Resort Thermae
La Posta Hotel & Thermal Spa
5 out of 5
  • 22 min drive from Castiglion del Bosco Winery
The price is $454 per night from May 7 to May 8
$454
includes taxes & fees
May 7 - May 8
Stay at this 5-star luxury hotel in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
La Posta Hotel & Thermal Spa
Mercure Petriolo Siena Terme Spa Hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 12 min drive from Castiglion del Bosco Winery
The price is $113 per night from May 12 to May 13
$113
includes taxes & fees
May 12 - May 13
Stay at this 5-star luxury hotel in Civitella Paganico. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Terme Petriolo and Castello ...
Mercure Petriolo Siena Terme Spa Hotel
Castel Porrona Relais & Spa
5 out of 5
  • 28 min drive from Castiglion del Bosco Winery
Stay at this 5-star luxury hotel in Cinigiano. Enjoy free breakfast, free WiFi, and free parking. Popular attractions House Museum of Monticello Amiata and Cantina ...
Castel Porrona Relais & Spa
Agriturismo San Fabiano
5 out of 5
  • 25 min drive from Castiglion del Bosco Winery
Stay at this 5-star luxury farm stay in Monteroni d'Arbia. Enjoy free WiFi, free parking, and an outdoor pool. Popular attraction Siena Circuit is located ...
Agriturismo San Fabiano
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5-Star Hotel in Castiglione del Bosco

It’s time. No more meh motels and so-so stays. This vacation it’s all about living it up, and that starts with a great hotel. You want first-class service and award-winning restaurants. Well, let us introduce you to a 5-star hotel in Castiglione del Bosco.

So nice you’ll blink twice

What makes a hotel worthy of supreme star-age? For starters, the service has to be top-notch and personalized. These hotels often have 24-hour room service, a welcome gift upon your arrival, and help you with your bags—even if you travel light.

Are they nicer? Heck yeah, they are! Most 5-star hotels have jaw-dropping aesthetics that give an authentic feel of class. And we’re not talking about that faux-gold soap dish your Aunt Tilda puts out for the guests—it’s the real deal.

Stars in your eyes

Are 5-stars hotels worth it? If you like the finer things in life, then yes, they sure are. But we also know you’re the type that likes to get your caviar on a fish stick budget. We’re right there with you, and that is why we make it easy to find the best 5-star hotel in Castiglione del Bosco for you. Sort by:

  • Price: Want to live large, but keep that budget balanced? We got you. We have 5-star hotels starting at $113.

  • Amenities: Castiglione del Bosco skyline view? Maybe a heated indoor pool? Looking for a Michelin-star restaurant? Search for the hotels that have the amenities you desire.

  • Hotwire Hot Rate: We’ll tell you the name of the hotel after you book, and you might just save a ton.

When you’re looking for the top 5-star hotels in Castiglione del Bosco—but don’t want to pay top dollar—let us help you out. You can get that posh palace of your dreams, and have money left to take on Castiglione del Bosco your way.