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

Castiglione del Bosco Hotels

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Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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Our top choices for Castiglione del Bosco hotels

A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.
A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.
A hotel room with a large bed, a bedside table, a lamp, a window with curtains, and a view of greenery outside.
A kitchen with a buffet setup, including a variety of food items and glassware.

1. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
Canada
Sam
€138
includes taxes & fees
31 Aug - 1 Sept
SI Montalcino Hotel
An aerial view of a historic town with stone buildings, a prominent church, and a castle-like structure with a sign reading "Castello di Monteverde."
An aerial view of a two-story stone building with a swimming pool in the foreground.
A room with a wooden bench, potted plants, framed artwork, and a view of the outside.
An outdoor patio with terracotta-tiled flooring, metal tables and chairs, potted plants, and a view of the sea.

2. Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
Montalcino
United States
Roy
€144
includes taxes & fees
28 Aug - 29 Aug
Hotel Vecchia Oliviera
A stone building with a tiled roof, a paved pathway, and a well-maintained garden.
A stone building with a pool, lounge chairs, and a garden with flowers.
A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.
A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

3. Podere Brizio

Podere Brizio
Montalcino
Mexico
Orlando Santini
€222
includes taxes & fees
30 Aug - 31 Aug
Podere Brizio
A stone-walled corridor with a wooden floor, a red flag, and a view into a courtyard.
A stone building with a tiled patio, wicker furniture, and potted plants.
A room with a large window, wooden floor, and a bed with a blue blanket.
A stone-walled wine cellar with wooden beams, a wooden table, and wine racks.

4. PALAZZO DEL CARDINALE

PALAZZO DEL CARDINALE
Montalcino
€124
includes taxes & fees
1 Sept - 2 Sept
PALAZZO DEL CARDINALE
A pool with a modern water feature and a stone structure.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.
A large, multi-story building with a swimming pool, surrounded by lush greenery.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

5. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
€83
includes taxes & fees
29 Aug - 30 Aug
Mercure Petriolo Siena Terme Spa Hotel
A pool with a stone wall, a view of the countryside, and a building with a tiled roof.
A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.
A hotel with a classic facade, multiple windows with shutters, and a sign indicating it is the "Hotel dei Capitani."
A buffet setup with various food items, a coffee station, and a counter with beverages.

6. Hotel Dei Capitani

Hotel Dei Capitani
Montalcino
United States
Frankie
€159
includes taxes & fees
30 Aug - 31 Aug
Hotel Dei Capitani
A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.
A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.
A stone building with the name "Albergoggiardino" above the entrance. Inside, there is a chandelier, a clock, and a blue chair.
A view from a window overlooking a rural landscape with fields and distant hills.

7. Albergo Giardino

Albergo Giardino
Montalcino
United Kingdom
Norma
€109
includes taxes & fees
31 Aug - 1 Sept
Albergo Giardino
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.
A bedroom with a bed, a nightstand, a lamp, a curtain, and a wooden door with a sign.
A spacious kitchen with wooden beams, a dining table with chairs, and a wooden cabinet.
A narrow hallway with wooden doors on either side, leading to a room with a tiled floor and a window with curtains.

8. Idolina Guest House

Idolina Guest House
Montalcino
United States
Bradley
€104
includes taxes & fees
8 Sept - 9 Sept
Idolina Guest House
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.
A stone building with a swimming pool, white lounge chairs, and a white umbrella.
A spacious living area with leather armchairs, a wooden cabinet with glass doors, and a red carpet.
A bedroom with a large bed, wooden beams on the ceiling, a nightstand with a lamp, and framed pictures on the wall.

9. Le Ragnaie

Le Ragnaie
Montalcino
United States
Douglas
€204
includes taxes & fees
13 Sept - 14 Sept
Le Ragnaie
A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.
A historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.
A living room with a white sofa, a coffee table, and a painting of a historical scene. There is a lamp, a small table with a plant, and a sign indicating room numbers.
A restaurant with a high ceiling, brick walls, and a bar area with a variety of bottles. There are tables and chairs for dining, and a television is visible on the right side.

10. Hotel Borgo Antico

Hotel Borgo Antico
Monteroni d'Arbia
United Kingdom
Charles
€88
includes taxes & fees
27 Aug - 28 Aug
Hotel Borgo Antico
A poolside area with lounge chairs, a table with drinks, and a view of hills.
An open door leading to a patio with a view of the countryside, a table with plants, and a television on a wooden cabinet.
A room with a large window, a door, and a view of a landscape.
A villa with a swimming pool, stone buildings, and a view of the surrounding countryside.

11. Capanna Suites

Capanna Suites
Montalcino
United States
Michael
€430
includes taxes & fees
29 Aug - 30 Aug
Capanna Suites
A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.
A table with a bottle of Brunello di Montalcino wine, a plate of food, and a bowl of bread.
A window with a view of a green landscape, including trees and distant hills.
A rustic interior with a brick fireplace, wooden beams, and a bar area.

12. Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
United States
Marko
€137
includes taxes & fees
30 Aug - 31 Aug
Fattoria Pieve a Salti
A bedroom with a bed, a chair, a table, and a stone wall.
An outdoor patio with stone walls, a pergola, and a table set for dining.
An underground wine cellar with brick walls, wooden tables, and chairs.
An underground wine cellar with wooden tables, wine bottles, and a piano.

13. Dimora delle Muse

Dimora delle Muse
Montalcino
United States
Bradley N.
€186
includes taxes & fees
28 Aug - 29 Aug
Dimora delle Muse
A person relaxing in a hot tub with a view of a vineyard and mountains in the background.
A pathway flanked by tall, narrow trees leading to a stone building with an arched entrance.
A picnic setup with blankets and cushions on a gravel surface, surrounded by cypress trees and a sunset in the background.
A dining area with a wooden table set for a meal, a fireplace, and a painting on the wall.

14. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
United States
Jeffery
€480
includes taxes & fees
29 Aug - 30 Aug
Villa Le Prata - Residenza del Vescovo
A hot tub with a view of a historic building and mountains.
A bedroom with a large window overlooking a castle, a bed, and a mirror on the wall.
A wine cellar with wooden racks and tables, a sign reading "DROGHERIA," and a rustic ceiling.
A staircase with stone steps leading to a room with a large window, wooden beams on the ceiling, and a stone wall.

15. Drogheria & Locanda Franci

Drogheria & Locanda Franci
Montalcino
United States
Nate
€196
includes taxes & fees
1 Sept - 2 Sept
Drogheria & Locanda Franci
A person serving food at a table with various dishes and a wine rack in the background.

16. Palazzo Lucchini

Palazzo Lucchini
Montalcino
€441
includes taxes & fees
27 Aug - 28 Aug
Palazzo Lucchini
A dining area with a table set for four, chairs, a television mounted on the wall, and a cabinet with glass doors.
A bedroom with a bed, two bedside tables with lamps, a window with curtains, and a painting on the wall.
A staircase with a metal railing leading to a landing.
A brick building with two windows and wooden shutters, surrounded by greenery.

17. L'Aia di Argia

L'Aia di Argia
Monteroni d'Arbia
United States
mario
€76
includes taxes & fees
27 Aug - 28 Aug
L'Aia di Argia
A spacious indoor area with a brick archway leading to a kitchen, wooden tables and chairs, and large windows offering a view of the outdoors.
An outdoor patio with brick flooring and metal furniture, surrounded by a brick building and greenery.
A historic building with a sign reading "HOTEL MORE DI CUNA". It features a brick facade, multiple windows, and an arched entrance.
A rocking chair with a cushion and a pillow, positioned against a wall with a tiled floor.

18. Hotel More Di Cuna

Hotel More Di Cuna
Monteroni d'Arbia
Australia
Vanessa
€111
includes taxes & fees
6 Sept - 7 Sept
Hotel More Di Cuna
A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.
A breakfast buffet with pastries, bread, and condiments.
A stone building with a view of a courtyard, a pool, and surrounding greenery.
A woman in a green swimsuit standing in a pool with a stone wall and a glass ceiling.

19. L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
United States
Stimson
€126
includes taxes & fees
30 Aug - 31 Aug
L'Orto delle Terme
A stone building with a courtyard and a canal.
A stone patio with a round table and chairs, surrounded by potted plants, overlooking a hilly landscape.
A bedroom with a wooden ceiling, a bed with a decorative headboard, a bench, and a large wardrobe.
A spacious room with a large bed, two armchairs, a sofa, and a view of the outdoors through a large window.

20. Palazzo Brandano

Palazzo Brandano
Trequanda
United Kingdom
Andrew
€88
includes taxes & fees
27 Aug - 28 Aug
Palazzo Brandano
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Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

9.6/10 (5 reviews)
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
A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.
Photo by tom owens

Top Castiglione del Bosco Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"We had an exceptional nice stay. I can highly recommend the Corsignano to anyone. It’s just a couple minutes walking distance from the old town … I will definitely stay here again on my next visit to Pienza"
Rene 1-night trip
Posted 20 hours ago
Hotel Corsignano
Hotel Italia

Hotel Italia

10/10 Excellent
"Staff were most courteous, both at front desk (local map offered on checkin) and in breakfast room. Breakfast buffet offered plenty of choices. Room and bathroom clean and tidy. City attractions dispersed throughout city, but walking made them accessible."
Catherine 4-night trip
Posted 1 day ago
Hotel Italia
Hotel Minerva

Hotel Minerva

10/10 Excellent
"Had a very nice stay here during the Palio. Easy walk to IL Campo. Located in the Lupa Contrada. Nice neighborhood. Easy walk (10-15 minutes) to the train station. Will stay here again when I return to Siena."
Moses 2-night trip
Posted 3 days ago
Hotel Minerva
L'Orto delle Terme

L'Orto delle Terme

8/10 Good
"Nice hotel and good location"
ANDRES 2-night trip
Posted 4 days ago
L'Orto delle Terme
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Tyler 1-night trip
Posted 8 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Athena

Hotel Athena

10/10 Excellent
"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."
Christopher 7-night trip
Posted 9 days ago
Hotel Athena
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."
Amy 2-night trip
Posted 12 days ago
Castello di Velona Resort Thermal SPA & Winery
Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World

10/10 Excellent
"Perfect, pristine, could not be any better!"
Zachary 1-night trip
Posted 3 weeks ago
Mastrojanni Relais - Small Luxury Hotels of the World
Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel

10/10 Excellent
"Las habitaciones son super lindas y espaciosas. El desayuno es completo y variado. Estuve con mi familia muy a gusto. Fue una estancia placentera. Lo recomiendo."
patricia 3-night trip
Posted 1 month ago
Mercure Petriolo Siena Terme Spa Hotel

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
€78
28 Aug - 29 Aug
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
€97
27 Aug - 28 Aug
includes taxes & fees
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
€98
27 Aug - 28 Aug
includes taxes & fees
8.8/10 Excellent! (104 reviews)
Albergo Centrale
Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
€114
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (211 reviews)
Hotel La Terrazza di Montepulciano
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
€129
29 Aug - 30 Aug
includes taxes & fees
10/10 Exceptional! (48 reviews)
Torre del Fuggisole
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get rates
9.4/10 Exceptional! (23 reviews)
Porta Pispini Residence

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 Grand Hotel Continental Siena – Starhotels Collezione. 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?
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This holiday home rental outside of Castiglione del Bosco is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of books so that you can immerse yourself in your holiday. 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?
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 3400 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 Tenuta Greppo Franco Biondi Santi 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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