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

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Our top choices for Castiglione del Bosco hotels

1. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (79 reviews)
"Wonderful stay "
United States
Talib
The price is AU$2,798
includes taxes & fees
2 Aug - 3 Aug
Castiglion del Bosco, A Rosewood Hotel

2. SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (398 reviews)
"Home away from home."
United States
Kristen
The price is AU$197
includes taxes & fees
3 Aug - 4 Aug
SI Montalcino Hotel

3. Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (147 reviews)
"Really enjoyed my stay here. Felt like I found a little gem of a place for the Tuscany part of our trip. Very well maintained, very attentive staff, pool was lovely and food at dinner was excellent. Would recommend."
United States
Michael
The price is AU$520
includes taxes & fees
25 Aug - 26 Aug
Capanna Suites

4. Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (163 reviews)
"Beautiful hotel, near to Montalcino and a lot winerys, very calm and charm the property Good breakfast Staff very kindly and attentive I recommend!!!!"
Mexico
Orlando Santini
The price is AU$394
includes taxes & fees
27 July - 28 July
Podere Brizio

5. Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (328 reviews)
"I would not change a thing. It was amazing great hospitality nice clean. I would definitely go back. Highly recommended."
United States
Jeton
The price is AU$327
includes taxes & fees
20 Aug - 21 Aug
Le Ragnaie

6. Drogheria & Locanda Franci

Drogheria & Locanda Franci
Montalcino
10.0 out of 10, Exceptional, (25 reviews)
"Would stay here again."
United States
Martin
The price is AU$302
includes taxes & fees
1 Aug - 2 Aug
Drogheria & Locanda Franci

7. Hotel Dei Capitani

Hotel Dei Capitani
3.0 star property
Montalcino
8.8 out of 10, Excellent, (449 reviews)
"Very nice place. If we have a chance to stay with them again we certainly will’"
United States
Frankie
The price is AU$260
includes taxes & fees
24 Aug - 25 Aug
Hotel Dei Capitani

8. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (86 reviews)
"Great location. Great wine. Great staff. "
United States
Vincenzo
The price is AU$839
includes taxes & fees
26 July - 27 July
Villa Le Prata - Residenza del Vescovo

9. Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
3.0 star property
Montalcino
9.4 out of 10, Exceptional, (70 reviews)
"Terrific breakfast! Lovely pool with gorgeous mountain views"
United States
Roy
The price is AU$242
includes taxes & fees
26 July - 27 July
Hotel Vecchia Oliviera

10. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (255 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is AU$153
includes taxes & fees
27 July - 28 July
Mercure Petriolo Siena Terme Spa Hotel

11. PALAZZO DEL CARDINALE

PALAZZO DEL CARDINALE
Montalcino
The price is AU$171
includes taxes & fees
27 July - 28 July
PALAZZO DEL CARDINALE

12. Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
9.0 out of 10, Wonderful, (42 reviews)
"Super stay !! "
Canada
Patryk
The price is AU$226
includes taxes & fees
26 July - 27 July
Fattoria Pieve a Salti

13. Dimora delle Muse

Dimora delle Muse
Montalcino
10.0 out of 10, Exceptional, (71 reviews)
"The breakfast was great. Sara and Michele are great hosts and have great recommendations for their guests. Very good place to stay. "
United States
Bradley N.
The price is AU$269
includes taxes & fees
27 July - 28 July
Dimora delle Muse

14. Hotel Borgo Antico

Hotel Borgo Antico
3.0 star property
Monteroni d'Arbia
8.8 out of 10, Excellent, (101 reviews)
"A hidden gem on the Via Francigena. We loved our stay after a day of walking from Siena. Delicious food too. "
United Kingdom
Charles
The price is AU$122
includes taxes & fees
23 Aug - 24 Aug
Hotel Borgo Antico

15. Hotel More Di Cuna

Hotel More Di Cuna
3.0 star property
Monteroni d'Arbia
9.0 out of 10, Wonderful, (34 reviews)
"Wonderful property! Very attractive rooms, common areas and great restaurant! "
United States
Leigh
The price is AU$117
includes taxes & fees
26 July - 27 July
Hotel More Di Cuna

16. Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
9.8 out of 10, Exceptional, (75 reviews)
"Wonderfully Beautiful Winery… Stunning views. Fabulous rooms and very welcoming staff."
United States
Laura
The price is AU$862
includes taxes & fees
8 Aug - 9 Aug
Mastrojanni Relais - Small Luxury Hotels of the World

17. Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.4 out of 10, Exceptional, (169 reviews)
"Nice hotel and a fantastic breakfast"
Norway
Inger Johanne
The price is AU$183
includes taxes & fees
26 July - 27 July
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

18. La Dimora di Roberta

La Dimora di Roberta
Montalcino
The price is AU$235
includes taxes & fees
7 Aug - 8 Aug
La Dimora di Roberta

19. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.6 out of 10, Exceptional, (121 reviews)
"Absolutely stunning property and views. The resort was very peaceful and we will definitely stay again in the future!"
United States
MarĆ­a
The price is AU$370
includes taxes & fees
14 Aug - 15 Aug
Borgo Sant'Ambrogio Resort

20. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
5.0 star property
Montalcino
9.0 out of 10, Wonderful, (360 reviews)
"An exceptional hotel. One of the most thoroughly enjoyable weeks we’ve had as a couple. Truly stunning surroundings with fantastic amenities. Cannot wait to go back!"
United Kingdom
Rachael
The price is AU$900
includes taxes & fees
24 Aug - 25 Aug
Castello di Velona Resort Thermal SPA & Winery
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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A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.
Photo by tom owens
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Frequently asked questions

What is the best area to stay in Castiglione Del Bosco?
The best area to stay in Castiglione Del Bosco is within the estate itself, specifically around the Borgo, as it offers the most convenient access to all amenities and services.

The Borgo is the heart of Castiglione Del Bosco, a beautifully restored historic village that serves as the central hub for guests. It's where you'll find the main reception, the estate's finest restaurants, and many of the facilities. The buildings are traditional Tuscan stone, and the entire area is designed for easy pedestrian access, allowing you to stroll between dining options, the spa, and the main pool with ease.

For couples seeking a luxurious and relaxing escape, staying within the Borgo or in one of the nearby suites is ideal. You'll be steps away from gourmet dining experiences, wine tastings at the estate's winery, and the indulgent spa treatments. The picturesque surroundings and the ease of access to all facilities make it superb for a stress-free romantic getaway.

Families will also find staying within the Borgo or in a nearby villa highly convenient. The proximity to the main pool, children's activities, and various dining options simplifies planning.
When is the best time to go to Castiglione Del Bosco?
The best time to go to Castiglione Del Bosco is during the spring (April to June) and autumn (September to October) months.

These periods offer pleasant weather, ideal for exploring the Tuscan countryside and enjoying the estate's amenities. Spring brings blooming wildflowers and comfortable temperatures, while autumn provides beautiful foliage and the excitement of the grape harvest season. Both seasons allow for outdoor activities without the intense heat of summer.

Couples often find these shoulder seasons particularly appealing. The weather is superb for leisurely walks through the vineyards, relaxing by the pool, or enjoying al fresco dining with stunning views. The estate's focus on fine wine and culinary experiences aligns perfectly with the relaxed pace of these months.

For travellers interested in the region's agricultural heritage, autumn is especially rewarding. You might witness grape harvesting or olive picking, offering a deeper connection to the local traditions and the estate's operations.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Castiglione del Bosco.
How can I save on a hotel booking in Castiglione del Bosco with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Castiglione del Bosco hotels. Plus, you'll earn OneKeyCashā„¢* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Castiglione del Bosco?
Prices for hotels in Castiglione del Bosco often vary, but you can find a great deal from AU$117 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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