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Find hotels in Castiglione del Bosco from ￥12,847

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Our top choices for Castiglione del Bosco hotels

Villa (Agresto) | Living area | LCD TV, pay movies
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)
Nestled in Montalcino, this lavish hotel offers Italian dining at Campo del Drago restaurant, rejuvenating spa treatments, and an exclusive golf course. Enjoy the poolside bar and rooftop terrace while nearby wineries beckon exploration.
"Wonderful stay "
United States
Talib
The price is ￥188,655
￥209,347 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Castiglion del Bosco, A Rosewood Hotel
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
Located steps from Siena's main square, this accommodation offers easy access to Museum of Torture and Palazzo Chigi-Saracini. Enjoy free WiFi and daily housekeeping, plus in-room coffeemakers. Travelers consistently praise the helpful staff.
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ￥19,119
￥21,761 total
includes taxes & fees
Dec 19 - Dec 20
PALAZZO DEL PAPA
Land view from property
Hotel Corsignano

Hotel Corsignano

Hotel Corsignano
4.0 star property
Pienza
9.4 out of 10, Exceptional, (330)
Discover this welcoming retreat near RI Crea RE and Enoteca Di Ghino attractions. Relax in 2 hot tubs after exploring historic Pienza. The restaurant serves local fare while the bar offers regional wines. Enjoy free WiFi and parking during your Tuscan adventure.
"Enjoyed the hotel. Great location, quality breakfast and rooms."
United States
Joseph
The price is ￥23,766
￥27,235 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel Corsignano
Terrace/patio
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1004)
This business-friendly hotel offers a scenic rooftop terrace, free WiFi, and complimentary parking. Guests praise the delicious breakfast and attentive staff. Sample local cuisine at Mangia restaurant, relax at the bar, or visit nearby National Museum of Archaeology.
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is ￥13,684
￥15,599 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hotel Athena
Outdoor banquet area
Palazzo Nobile di San Donato

Palazzo Nobile di San Donato

Palazzo Nobile di San Donato
Montepulciano
9.4 out of 10, Exceptional, (68)
Located near Consorzio del Vino Nobile and Palazzo Comunale, this distinctive B&B offers complimentary continental breakfast and WiFi. Outdoor enthusiasts will appreciate the nearby hiking and mountain biking trails, while room service adds extra convenience to your Tuscan getaway.
"Unique experience in a central location "
United States
Neil T
The price is ￥34,057
￥38,193 total
includes taxes & fees
Dec 14 - Dec 15
Palazzo Nobile di San Donato
Interior
Meublé Il Riccio

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86)
Panoramic views await at this Montepulciano hideaway, where the rooftop terrace offers breathtaking vistas. Just steps from historic Piazza Grande and Contucci winery, this charming hotel provides free WiFi, parking, and a garden oasis with morning buffet breakfast.
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Tasting room
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (191)
Enchanting Siena accommodation with a welcoming restaurant and bar/lounge for evening relaxation. Located near the historic Siena Baptistry and Crypt, this residence offers comfortable rooms with free WiFi and room service.
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Hiking
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.8 out of 10, Exceptional, (97)
Immerse yourself in rural luxury at this farm stay with helpful staff. Enjoy Italian dining at Borgo Sant'Ambrogio R restaurant, unwind by the seasonal pool, or explore nearby Monastery of Sant'Anna in Camprena. Free breakfast, WiFi and parking enhance your Tuscan retreat.
"It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!"
United States
Juan Carlos
The price is ￥16,776
￥19,001 total
includes taxes & fees
Dec 14 - Dec 15
Borgo Sant'Ambrogio Resort
Porch
Relais degli Angeli

Relais degli Angeli

Relais degli Angeli
Siena City Centre
9.8 out of 10, Exceptional, (281)
Set in the heart of Siena, this charming inn offers a rooftop terrace with city views. Hiking trails nearby provide outdoor adventure, while Palazzo Salimbeni and Piazza Salimbeni are just around the corner. Siena Station is an 18-minute walk away.
"Very central and walkable. Wonderful staff and room was clean and comfortable. "
United States
Kristin
The price is ￥20,173
￥22,919 total
includes taxes & fees
Dec 15 - Dec 16
Relais degli Angeli
Breakfast meal
B&B Il Corso

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (191)
Immersed in Siena's heart, this B&B offers premium bedding and free WiFi near Teatro dei Rozzi and Fonte Gaia. Daily housekeeping ensures comfort while you explore local attractions. Siena Station is just a 9-minute drive away.
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
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)
Just steps from iconic Piazza del Campo, this guesthouse combines prime location with comfort. Free WiFi and premium bedding enhance your stay while Museum of Torture and Palazzo Chigi-Saracini await nearby.
"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
Garden
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

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, (154)
Embrace local cuisine at Al Vecchio Forno restaurant after indulging in hot stone massages at the full-service spa. Explore nearby Horti Leonini gardens, then unwind on the terrace with garden views. Free WiFi and parking enhance your authentic Tuscan retreat.
"Nice informal environment, good staff, great ubication "
United States
norma
The price is ￥15,772
￥18,078 total
includes taxes & fees
Dec 15 - Dec 16
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
Terrace/patio
Residenza d'Epoca Relais Campo Regio

Residenza d'Epoca Relais Campo Regio

Residenza d'Epoca Relais Campo Regio
Siena City Centre
9.8 out of 10, Exceptional, (90)
This historic B&B in Siena offers free breakfast, room service, and massage treatments. The cozy bar creates a perfect spot to unwind after exploring nearby Casa di Santa Caterina and Fontebranda attractions.
"It was the best cleanliness and quality of service, warmth and so beautiful pleasant stay!!! )))"
United States
elina
The price is ￥33,951
￥38,075 total
includes taxes & fees
Dec 22 - Dec 23
Residenza d'Epoca Relais Campo Regio
Sundeck
Capanna Suites

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (131)
Italian elegance meets vineyard charm at this countryside retreat with on-site winery. After savoring local wines at the poolside bar, indulge in Italian cuisine at Il Passaggio by Capanna restaurant before relaxing with rejuvenating spa treatments.
"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
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
Wake up to views of Siena from this cozy residence offering free WiFi and daily housekeeping. Just minutes from Museum of Torture and Palazzo Chigi-Saracini, with convenient room service and a 15-minute drive to Siena Station.
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Food and drink
Hotel San Gregorio

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
Soak up the Italian countryside at this charming Tuscan residence featuring a seasonal outdoor pool and on-site restaurant serving local cuisine. Near RI Crea RE and Enoteca Di Ghino, with convenient room service, free WiFi, and a relaxing garden and bar.
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is ￥31,842
￥36,119 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel San Gregorio
Interior
La Dimora Dei Monaci

La Dimora Dei Monaci

La Dimora Dei Monaci
Siena City Centre
10.0 out of 10, Exceptional, (86)
Just 5 minutes from Piazza del Campo, this charming Siena B&B offers free WiFi and daily housekeeping. Explore San Spirito and San Martino attractions, with Siena Station only a 14-minute drive away.
"Fantastic accommodations! Very comfortable bed! Spacious room, and beautiful. We definitely recommend."
United States
Karin
La Dimora Dei Monaci
Down comforters, minibar, in-room safe, individually decorated
Quattro Cantoni

Quattro Cantoni

Quattro Cantoni
Siena City Centre
8.8 out of 10, Excellent, (80)
Charming B&B in the heart of Siena offers free WiFi and convenient airport shuttle service. Just moments from Pinacoteca Nazionale and the Natural History Museum, this cozy retreat puts Italian cultural gems at your doorstep.
"Absolutely loved this stay. The staff were incredibly helpful and got me taxis etc when I needed them. The room was so comfortable with high tech support for working and relaxing. The meals were absolutely delicious and served with great customer service. This was a gem of a place to stay. The area is also beautiful and has much to offer in terms of a relaxing stay. I would happily go again! "
United Kingdom
Yvonne
The price is ￥12,073
￥14,010 total
includes taxes & fees
Dec 14 - Dec 15
Quattro Cantoni
Property entrance
Il Tosco

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (115)
Experience Italian elegance at this luxury residence in Montepulciano's entertainment district. Enjoy La Cucina's authentic Italian cuisine, convenient room service, and a stylish bar/lounge. Just minutes from Torre del Pulcinella with free WiFi and parking for seamless exploration.
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is ￥39,507
￥44,187 total
includes taxes & fees
Dec 22 - Dec 23
Il Tosco
Room amenity
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
Set adjacent to a golf course with easy access to Fontebranda and Piccolomini Library. This hotel offers refrigerators and microwaves in rooms, plus free WiFi and room service. Guests love the helpful staff and clean accommodations.
"A great location!"
Canada
Cheryl
Siena Vip
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 out? 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

Villa del Sole Siena

Villa del Sole Siena

10/10 Excellent
"Amazing rooms and service!!"
Janet 1-night trip
Posted 4 days ago
Villa del Sole Siena

More cheap stays in Castiglione del Bosco

Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
The price is ￥11,407 per night from Dec 15 to Dec 16
￥11,407
￥13,095 total
Dec 15 - Dec 16
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 traveler data. This hotel offers a winery and 2 outdoor pools. Two other options for your stay in the area are Hotel Athena and Palazzo Ravizza. See all available top hotels, or vacation rentals in Castiglione del Bosco.
What's the top vacation rental in Castiglione del Bosco?
The House of Alice, charm and relaxation: Visitors like this Castiglione del Bosco vacation home rental. It 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 kitchenware. 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, you'll find most hotel bookings are refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Castiglione del Bosco.
Where can I learn more about changing or cancelling my trip to Castiglione del Bosco?
For additional details about changing or cancelling your trip to Castiglione del Bosco, go to https://www.expedia.com/service/.
What's the best boutique-style accommodation in Castiglione del Bosco?
Castiglion del Bosco, A Rosewood Hotel is a favorite hotel with our travelers looking for a stylish accommodation, and features 42 guestrooms, a winery, and 2 restaurants. See all boutique hotels in Castiglione del Bosco.
What's the best place to stay near Peretola Airport (FLR)?
Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.
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 accommodations in the surrounding area. Find out more about Castiglione del Bosco.
What is there to see in Castiglione del Bosco?
A favorite place to visit is Castiglion del Bosco Winery. You'll also find Fortress of Montalcino and Castello di Montepescini in the area. Check out what more 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 temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castiglione del Bosco is 37 inches.

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