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6 Dec - 7 Dec
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Top hotels and accommodation in Castiglione del Bosco

2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, pool loungers
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5.0 star property
Montalcino
10.0 out of 10, Exceptional, (69)
"the pool area is undoubtedly lovely. it would have been more enjoyable with a higher water temperature"
United States
Jaime
Travelling for leisure
The price is AU$2,334
includes taxes & fees
12 Dec - 13 Dec
Castiglion del Bosco, A Rosewood Hotel
Jetted bathtub
Grand Hotel Impero - Wellness & Exclusive SPA

Grand Hotel Impero - Wellness & Exclusive SPA

4.0 star property
Castel del Piano
9.2 out of 10, Wonderful, (81)
"The attached restaurant had very good food as well."
Canada
Sherri
Travelling with family
The price is AU$145
includes taxes & fees
16 Dec - 17 Dec
Grand Hotel Impero - Wellness & Exclusive SPA
Villa, Valley View | Garden view
Drogheria & Locanda Franci

Drogheria & Locanda Franci

Montalcino
9.8 out of 10, Exceptional, (16)
"Nice room on a perfect location to walk around Montalcino with easy parking!"
United States
Alejandro
Travelling for leisure
The price is AU$419
includes taxes & fees
21 Dec - 22 Dec
Drogheria & Locanda Franci
Lunch and dinner served, local cuisine
La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa

5.0 star property
San Quirico d'Orcia
9.6 out of 10, Exceptional, (70)
"The restaurant have fabulous healthy breakfast and dinner ."
United States
Teresita
Travelling with family
The price is AU$682
includes taxes & fees
10 Dec - 11 Dec
La Posta Hotel & Thermal Spa
Garden
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

5.0 star property
Trequanda
9.8 out of 10, Exceptional, (97)
"The property is absolutely beautiful with breathtaking views of the Tuscan landscape."
United States
Richard
Travelling for leisure
The price is AU$191
includes taxes & fees
8 Dec - 9 Dec
Borgo Sant'Ambrogio Resort
Restaurant
Palazzo Nobile di San Donato

Palazzo Nobile di San Donato

Montepulciano
9.4 out of 10, Exceptional, (67)
"Great location, nice and helpful staff and fantastic food for the breakfast and the recommended restaurant."
United States
Vasile
Travelling for leisure
The price is AU$353
includes taxes & fees
9 Dec - 10 Dec
Palazzo Nobile di San Donato
Land view from property
Hotel Corsignano

Hotel Corsignano

4.0 star property
Pienza
9.4 out of 10, Exceptional, (329)
"Nice location very convenient if you like to avoid driving after your wine with dinner."
United States
Jane
The price is AU$225
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel Corsignano
Terrace/patio
Castello

Castello

3.0 star property
Sovicille
8.6 out of 10, Excellent, (70)
"Great little place to stay overnight. "
United States
Ivona
Castello
Royal Room, Balcony, Mountain View
Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo

Roccastrada
The price is AU$148
includes taxes & fees
9 Dec - 10 Dec
Historic Farmhouse Casa del Chiodo
Free daily continental breakfast
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4.0 star property
Pienza
8.8 out of 10, Excellent, (629)
"Clean, spacious room and the bathroom was huge."
United States
Karlene
Travelling for leisure
Hotel Relais II Chiostro di Pienza
View from property
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, (339)
"Beautiful views, wonderful pool and spa, delicious food."
United States
Betty
Travelling with partner
Castello di Velona Resort Thermal SPA & Winery
Front of property – evening/night
Relais Le Macine di Stigliano

Relais Le Macine di Stigliano

4.0 star property
Sovicille
10.0 out of 10, Exceptional, (15)
"The restaurant is super delicious."
United States
Daniel
Travelling for leisure
The price is AU$228
includes taxes & fees
8 Dec - 9 Dec
Relais Le Macine di Stigliano
Front of property
Rossellino

Rossellino

Pienza
8.6 out of 10, Excellent, (55)
"Welcoming people and clean room, but the wow factor is the roof view of the entire area."
United States
James
Travelling for leisure
The price is AU$220
includes taxes & fees
11 Dec - 12 Dec
Rossellino
Seasonal outdoor pool, open 9:30 AM to 7:30 PM, pool umbrellas
Le Ragnaie

Le Ragnaie

Montalcino
9.2 out of 10, Wonderful, (323)
"Our room was spacious, clean and beautifully appointed, offering great comfort and charm."
Canada
Jess
Travelling with family
Le Ragnaie
Exterior
Capanna Suites

Capanna Suites

Montalcino
9.8 out of 10, Exceptional, (130)
"Nicely decorated, big bathroom & shower."
United States
Linda
Travelling with family
Capanna Suites
Front of property
Albergo Le Terme

Albergo Le Terme

4.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (68)
"Very good hotel. The parking is a little bit far, good breakfast, i will recommend 👌 "
United States
liad
The price is AU$800
includes taxes & fees
27 Dec - 28 Dec
Albergo Le Terme
Seasonal outdoor pool, pool umbrellas, pool loungers
Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

4.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (228)
"The property and the room was beautiful."
United States
Kyla
The price is AU$331
includes taxes & fees
10 Dec - 11 Dec
Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection
Superior Double Room, 1 Queen Bed, Valley View (Superior)
Locanda In Tuscany

Locanda In Tuscany

Castiglione d'Orcia
9.6 out of 10, Exceptional, (19)
"Our stay at Locanda in Tuscany was nothing short of spectacular. Nestled in the heart of the Tuscan countryside, the hotel offers breathtaking views that capture the essence of this picturesque region. The staff were exceptional, anticipating our needs and promptly responding to all our requests, from arranging wine tastings to making dining reservations. The rooms were beautifully appointed with luxurious amenities that blended seamlessly with the rustic charm of the surroundings. Our daughter...
India
Shashidhar
The price is AU$445
includes taxes & fees
7 Dec - 8 Dec
Locanda In Tuscany
Exterior
Locanda Vesuna

Locanda Vesuna

3.0 star property
Trequanda
9.4 out of 10, Exceptional, (50)
"Such a quiet and beautiful property, the hosts provided everything that was needed, and the location was great for visiting local Cantinas and Vineyards "
United States
Justin
The price is AU$153
includes taxes & fees
19 Dec - 20 Dec
Locanda Vesuna
Dining
Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence

Roccastrada
9.4 out of 10, Exceptional, (28)
"pretty setting"
Canada
ed
Valdonica Winery & Vineyard Residence
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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Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.
See properties

Learn more about Castiglione del Bosco

Love history and dining? Get away to Castiglione del Bosco!

See all hotels in Castiglione del Bosco
Beautiful view of the hotel pool (a number of the villas have their own pools) from a terrace above, with the Tuscan hillside in the background.
Photo by tom owens
Open Photo by tom owens

Top Castiglione del Bosco Hotel Reviews

Recent Reviews in Castiglione del Bosco

Hotel Italia

Hotel Italia

10/10 Excellent
"Clean room, helpful staff and excellent breakfast"
Simin 1-night trip
Posted 4 days ago
Hotel Italia

More cheap accommodation in Castiglione del Bosco

Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
The price is AU$140 per night from 20 Dec to 21 Dec
AU$140
20 Dec - 21 Dec
includes taxes & fees
7.8/10 Good! (388 reviews)

Frequently asked questions

What's the best place to stay in Castiglione del Bosco?
Rosewood Castiglion del Bosco is one of the top choices for your stay based on our traveller data. This hotel offers a winery and 2 outdoor pools. Other good options for your trip to the area are Hotel Athena and Palazzo Ravizza. See all available top hotels, or vacation rentals in Castiglione del Bosco.
What are some of the best holiday rentals that Castiglione del Bosco has to offer?
The House of Alice, charm and relaxation: This holiday home rental outside of Castiglione del Bosco is located in a rural location, and has a fireplace, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. Kick off your shoes and enjoy yourself with a garden and a selection of books. See all vacation rentals in Castiglione del Bosco.
If I need to cancel my hotel reservation in Castiglione del Bosco, will I receive a refund?
Yes! Most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Castiglione del Bosco.
What's the best boutique-style hotel in Castiglione del Bosco?
Rosewood Castiglion del Bosco is a favourite hotel with our travellers looking for stylish accommodation, and features 42 guestrooms, a winery and 2 restaurants. See all boutique hotels in Castiglione del Bosco.
What is staying in Castiglione del Bosco like?
Visitors can enjoy all that Castiglione del Bosco has to offer, including its restaurants. Tourists to the city can also enjoy its welcoming locals. There are 3253 hotels and other accommodation options in the surrounding area. Find out more about Castiglione del Bosco.
What should I do while I'm visiting Castiglione del Bosco?
A favourite place to visit is Castiglion del Bosco Winery. You'll also find Fortress of Montalcino and Castello di Montepescini in the area. Take a look at what more there is to see and do in Expedia's Castiglione del Bosco guide.
What's the weather like in Castiglione del Bosco?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castiglione del Bosco is 944 mm.

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