Photo by tom owens

Castiglione del Bosco Hotels from S$95

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Castiglione del Bosco hotels

Living area
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (69)
"Wonderful stay "
United States
Talib
The price is S$1,966
includes taxes & fees
4 Jan - 5 Jan, 2026
Castiglion del Bosco, A Rosewood Hotel
Outdoor pool, a rooftop pool, pool loungers
Castello di Leonina Relais

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (120)
"Perfectb Quiet and very relaxing stay. Breakfast was very tasty and the view was absolutely spectacular "
United Kingdom
Mayara
The price is S$220
includes taxes & fees
27 Dec - 28 Dec
Castello di Leonina Relais
Hiking
Palazzo Brandano

Palazzo Brandano

Palazzo Brandano
Trequanda
9.6 out of 10, Exceptional, (73)
"Excellent breakfast experience with farm fresh food with good service by staff. Spacious parking lot behind the property."
United States
KEVIN
The price is S$95
includes taxes & fees
17 Dec - 18 Dec
Palazzo Brandano
Property entrance
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
5.0 star property
Siena City Centre
9.2 out of 10, Wonderful, (574)
"Great hotel / room, city center, friendly staff. "
United States
Nebojsa
The price is S$433
includes taxes & fees
14 Jan - 15 Jan, 2026
Grand Hotel Continental Siena – Starhotels Collezione
Terrace/patio
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1008)
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is S$130
includes taxes & fees
8 Jan - 9 Jan, 2026
Hotel Athena
Breakfast meal
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (746)
"We enjoyed our stay here."
United States
LAURIA
The price is S$152
includes taxes & fees
21 Dec - 22 Dec
Palazzo Ravizza
Terrace/patio
Villa del Sole Siena

Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (627)
"Beautiful small hotel with an exceptional staff. "
United States
Raymond
The price is S$210
includes taxes & fees
23 Dec - 24 Dec
Villa del Sole Siena
Lobby sitting area
Locanda Vesuna

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.4 out of 10, Exceptional, (52)
"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 S$131
includes taxes & fees
19 Dec - 20 Dec
Locanda Vesuna
Front of property
Hotel Italia

Hotel Italia

Hotel Italia
3.0 star property
Camollia
9.2 out of 10, Wonderful, (1001)
"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is S$99
includes taxes & fees
11 Jan - 12 Jan, 2026
Hotel Italia
Sun deck
Capanna Suites

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (131)
"Absolutely amazing resort with amazing staff and service. Great food and beautiful spa experience. Highly reccommend anyone going to Tuscany to book here - you will not be disappointed ! "
Canada
Megan
Capanna Suites
View from property
Castello di Velona Resort Thermal SPA & Winery

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, (340)
"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."
United States
Jose
Castello di Velona Resort Thermal SPA & Winery
Front of property
Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
4.0 star property
Siena
9.8 out of 10, Exceptional, (185)
"The best in Siena."
Canada
David
The price is S$330
includes taxes & fees
22 Dec - 23 Dec
Hotel Certosa Di Maggiano
Interior
Hotel Chiusarelli

Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1001)
"Lovely staff and great location with a quiet, comfortable room."
United States
Katherine
The price is S$125
includes taxes & fees
9 Jan - 10 Jan, 2026
Hotel Chiusarelli
Spa
Mastrojanni Relais

Mastrojanni Relais

Mastrojanni Relais
Montalcino
10.0 out of 10, Exceptional, (61)
"This is the most magical and beautiful property in Tuscany with amazing food and service. The guests talk about how they come back every year to this resort The views from the pool are the best in this area. "
United States
Laura
The price is S$614
includes taxes & fees
20 Dec - 21 Dec
Mastrojanni Relais
Room amenity
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
Siena Vip
Front of property
B&B Le Aquile

B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (111)
"Staff was exceptionally helpful prior to arriving at property and offering suggestions for transportation to surrounding activities. Location was well situated to highlights and attractions. "
Canada
Lydia
B&B Le Aquile
Porch
Relais degli Angeli

Relais degli Angeli

Relais degli Angeli
Siena City Centre
9.8 out of 10, Exceptional, (281)
"Very central and walkable. Wonderful staff and room was clean and comfortable. "
United States
Kristin
The price is S$191
includes taxes & fees
21 Dec - 22 Dec
Relais degli Angeli
Exterior
Albergo Le Terme

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 S$641
includes taxes & fees
27 Dec - 28 Dec
Albergo Le Terme
Breakfast meal
B&B Il Corso

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (191)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
View from property
Hotel Alma Domus

Hotel Alma Domus

Hotel Alma Domus
1.0 star property
Siena City Centre
8.8 out of 10, Excellent, (773)
"Great breakfast, clean rooms and wonderful area"
Canada
Treena
Hotel Alma Domus
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"The best in Siena."
David 1-night trip
Posted 3 days ago
Hotel Certosa Di Maggiano

More cheap stays in Castiglione del Bosco

Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
The price is S$115 per night from 18 Dec to 19 Dec
S$115
18 Dec - 19 Dec
includes taxes & fees
8.8/10 Excellent! (89 reviews)

Frequently asked questions

What's the best place to stay in Castiglione del Bosco?
Castiglion del Bosco, A Rosewood Hotel 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.
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?
Castiglion del Bosco, A Rosewood Hotel 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 3270 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.

Explore a world of travel with Expedia