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, (86 reviews)
"Nice and quiet excellent hospitality"
United States
Mohammed
The price is NZ$2,483
includes taxes & fees
4 Nov - 5 Nov
Castiglion del Bosco, A Rosewood Hotel

2. SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (418 reviews)
"An excellent location for enjoying a peaceful atmosphere, surrounded by true nature and spectacular views. I would certainly stay at this Agriturismo again when I return to Tuscany."
United States
Farasley
The price is NZ$217
includes taxes & fees
6 Nov - 7 Nov
SI Montalcino Hotel

3. Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (177 reviews)
"Lovely setting. Great views and incredibly helpful staff. Really enjoyed our two days. Can’t wait to come back 👍"
United States
Aseem
The price is NZ$386
includes taxes & fees
17 Nov - 18 Nov
Podere Brizio

4. Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (342 reviews)
"Amazing stay very welcoming and gorgeous views!"
United States
Trevor
The price is NZ$215
includes taxes & fees
23 Nov - 24 Nov
Le Ragnaie

5. Hotel Borgo Antico

Hotel Borgo Antico
3.0 star property
Monteroni d'Arbia
8.8 out of 10, Excellent, (103 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 NZ$178
includes taxes & fees
31 Oct - 1 Nov
Hotel Borgo Antico

6. Wine Estate Paradiso di Cacuci

Wine Estate Paradiso di Cacuci
Montalcino
8.4 out of 10, Very good, (5 reviews)
"Very Small village Most beautiful view ever Excellent wine and excellent breakfast"
Canada
Maud
The price is NZ$542
includes taxes & fees
31 Oct - 1 Nov
Wine Estate Paradiso di Cacuci

7. Albergo Giardino

Albergo Giardino
Montalcino
8.8 out of 10, Excellent, (43 reviews)
"Albergo Giardino is in an ideal location, with a good choice of restaurants, bars and shops close by. It is clean, comfortable and in the heart of a thriving community. Owner Nida was lovely and keen to ensure a pleasant stay. Would recommend."
United Kingdom
Norma
The price is NZ$225
includes taxes & fees
2 Nov - 3 Nov
Albergo Giardino

8. Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
9.0 out of 10, Wonderful, (51 reviews)
"Most beautiful and relaxing place on the planet😁"
United States
Marko
The price is NZ$207
includes taxes & fees
1 Nov - 2 Nov
Fattoria Pieve a Salti

9. Casa Franci Montalcino

Casa Franci Montalcino
Montalcino
9.8 out of 10, Exceptional, (47 reviews)
"Fantastic accommodations, friendly and helpful staff"
United States
Jim
The price is NZ$516
includes taxes & fees
16 Nov - 17 Nov
Casa Franci Montalcino

10. Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (167 reviews)
"This is our new favorite place to stay near Montalcino. It is beautiful beyond words, and the rooms are fantastic, spacious, comfortable, and just perfect. We will be back!"
United States
Silvana
The price is NZ$586
includes taxes & fees
2 Nov - 3 Nov
Capanna Suites

11. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (267 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is NZ$164
includes taxes & fees
2 Nov - 3 Nov
Mercure Petriolo Siena Terme Spa Hotel

12. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (94 reviews)
"A lovely place to enjoy the wine and the region. Rooms are spacious and extremely clean. House has a magical feel to it. Staff were so kind and always on hand to help out. A wonderful visit!"
Canada
Karen
The price is NZ$822
includes taxes & fees
4 Nov - 5 Nov
Villa Le Prata - Residenza del Vescovo

13. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is NZ$513
includes taxes & fees
30 Nov - 1 Dec
Palazzo Saloni

14. Dimora delle Muse

Dimora delle Muse
Montalcino
10.0 out of 10, Exceptional, (75 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 NZ$361
includes taxes & fees
2 Nov - 3 Nov
Dimora delle Muse

15. Palazzuolo

Palazzuolo
3.0 star property
San Quirico d'Orcia
8.2 out of 10, Very good, (203 reviews)
"Very clean! helpful staff!. Nice location."
United States
Alberto
The price is NZ$401
includes taxes & fees
31 Oct - 1 Nov
Palazzuolo

16. Palazzo Lucchini

Palazzo Lucchini
Montalcino
The price is NZ$816
includes taxes & fees
31 Oct - 1 Nov
Palazzo Lucchini

17. Relais Cloister Pienza

Relais Cloister Pienza
4.0 star property
Pienza
9.4 out of 10, Exceptional, (13 reviews)
"Just a fantastic place in the most beautiful setting. Medieval historical ambiance with a modern vibe. Pool area - perfect. Breakfast - perfect. Dinner - perfect. Views - incredible! Location - the best in town!"
United States
Karen
The price is NZ$222
includes taxes & fees
2 Nov - 3 Nov
Relais Cloister Pienza

18. L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
9.6 out of 10, Exceptional, (63 reviews)
"Clean room and beautiful Suite. Breakfast was excellent!"
United States
Tracey
The price is NZ$246
includes taxes & fees
11 Nov - 12 Nov
L'Orto delle Terme

19. Palazzo Brandano

Palazzo Brandano
Trequanda
9.4 out of 10, Exceptional, (107 reviews)
"Large rooms, helpful staff, delicious breakfast at a very reasonable price. There’s no water by the hotel, as seen in the picture. It’s located on a very old walled town… quite quaint."
Canada
Peter
The price is NZ$107
includes taxes & fees
30 Nov - 1 Dec
Palazzo Brandano

20. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
9.6 out of 10, Exceptional, (83 reviews)
"The natural surroundings and views around the agriturismo were beautiful, making our stay truly enjoyable. The tours and dinner options provided are excellent as well — I highly recommend taking part in them."
Japan
RYO
The price is NZ$280
includes taxes & fees
19 Nov - 20 Nov
Agriturismo Il Macchione
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.

Hotels recommended for families in Castiglione del Bosco

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A stone staircase leading to a stone building surrounded by hedges.
Photo by Mario Mürner
Open Photo by Mario Mürner

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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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 programme—gives you instant access to discounts with Member Prices on Castiglione del Bosco hotels. Plus, you'll earn OneKeyCash™* 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 NZ$93 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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