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

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Oct 19 - Oct 20
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Oct 20 - Oct 21
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Our top choices for Castiglione del Bosco hotels

A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.
An aerial view of a villa with a swimming pool, terraced gardens, and a stone pathway.
An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.
An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.

1. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
Montalcino
United States
Mohammed
$1,225 nightly
$1,359 total
Nov 3 - Nov 4
Total with taxes and fees
Castiglion del Bosco, A Rosewood Hotel
A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.
A hotel room with a bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.
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.

2. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
United States
Farasley
$97 nightly
$116 total
Oct 29 - Oct 30
Total with taxes and fees
SI Montalcino Hotel
A stone building with a tiled roof, a paved pathway, and a well-maintained garden.
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.
A stone building with a wooden deck and white lounge chairs.

3. Podere Brizio

Podere Brizio
Montalcino
United States
Aseem
$200 nightly
$229 total
Oct 31 - Nov 1
Total with taxes and fees
Podere Brizio
A logo with a bird and a shield, and the text "AMARAVATI".
A room with red leather sofas, a glass coffee table, and potted plants.
A breakfast table with croissants, a pitcher, a teapot, and a vase with flowers.
A bar area with two people seated at a counter, a glass display case with bottles, and a vase with flowers on the wall.

4. Hotel Ghibellino

Hotel Ghibellino
Buonconvento
Australia
Anna-Maree
$89 nightly
$101 total
Oct 20 - Oct 21
Total with taxes and fees
Hotel Ghibellino
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.
An outdoor patio with stone walls, green cushioned seating, a table with chairs, and a decorative umbrella.
A bedroom with a large bed, wooden beams on the ceiling, a nightstand with a lamp, and framed pictures on the wall.

5. Le Ragnaie

Le Ragnaie
Montalcino
United States
Trevor
$99 nightly
$120 total
Oct 28 - Oct 29
Total with taxes and fees
Le Ragnaie
A pool with a stone wall, a view of the countryside, and a building with a tiled roof.
A hotel with a classic facade, multiple windows with shutters, and a sign indicating it is the "Hotel dei Capitani."
A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.
A terrace with outdoor seating, a view of the landscape, and a building with large windows.

6. Hotel Dei Capitani

Hotel Dei Capitani
Montalcino
United States
Phillip
$116 nightly
$137 total
Oct 21 - Oct 22
Total with taxes and fees
Hotel Dei Capitani
A pool with a modern water feature and a stone structure.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.
A large, multi-story building with a swimming pool, surrounded by lush greenery.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

7. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
Canada
Penny
$84 nightly
$93 total
Oct 20 - Oct 21
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.
A balcony with a wrought iron railing overlooking a village with terracotta rooftops and greenery.
A courtyard with outdoor seating, a building with multiple windows, and a stone wall.
A multi-story building with a central entrance, large windows with shutters, and a paved courtyard.

8. Palazzo Saloni

Palazzo Saloni
Montalcino
United States
Michael
$253 nightly
$289 total
Nov 18 - Nov 19
Total with taxes and fees
Palazzo Saloni
A person relaxing in a hot tub with a view of a vineyard and mountains in the background.
A dining area with a wooden table set for a meal, a fireplace, and a painting on the wall.
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.

9. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
Canada
Karen
$430 nightly
$485 total
Nov 5 - Nov 6
Total with taxes and fees
Villa Le Prata - Residenza del Vescovo
A hot tub with a view of a historic building and mountains.
A staircase with stone steps leading to a room with a large window, wooden beams on the ceiling, and a stone wall.
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.

10. Casa Franci Montalcino

Casa Franci Montalcino
Montalcino
United States
Joseph
$200 nightly
$232 total
Oct 21 - Oct 22
Total with taxes and fees
Casa Franci Montalcino
A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.
A view from a window overlooking a rural landscape with fields and distant hills.
A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.
A courtyard with a stone wall, a small pond, and a waterfall. There are trees and plants around, and a building in the background.

11. Albergo Giardino

Albergo Giardino
Montalcino
United Kingdom
Norma
$111 nightly
$131 total
Nov 18 - Nov 19
Total with taxes and fees
Albergo Giardino
A poolside area with lounge chairs, a table with drinks, and a view of hills.
A villa with a swimming pool, stone buildings, and a view of the surrounding countryside.
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 four-poster bed with a bench, stone flooring, and a stone wall.

12. Capanna Suites

Capanna Suites
Montalcino
United States
Michael
$325 nightly
$369 total
Oct 26 - Oct 27
Total with taxes and fees
Capanna Suites
A bedroom with a bed, a chair, a table, and a stone wall.
A piano with sheet music, an easel with a drawing, and a wine bottle in a stone-walled room.
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.

13. Dimora delle Muse

Dimora delle Muse
Montalcino
United States
Bradley N.
$167 nightly
$193 total
Nov 8 - Nov 9
Total with taxes and fees
Dimora delle Muse
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a gravel pathway leading to the entrance.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

14. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
South Korea
YOUNG BAE
$133 nightly
$151 total
Nov 19 - Nov 20
Total with taxes and fees
Agriturismo Il Macchione
A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.
A stone building with a view of a courtyard, a pool, and surrounding greenery.
A breakfast buffet with pastries, bread, and condiments.
A woman in a green swimsuit standing in a pool with a stone wall and a glass ceiling.

15. L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
United States
Tracey
$117 nightly
$133 total
Nov 18 - Nov 19
Total with taxes and fees
L'Orto delle Terme
A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.
A rustic interior with a brick fireplace, wooden beams, and a bar area.
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.

16. Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
United States
Marko
$112 nightly
$128 total
Nov 9 - Nov 10
Total with taxes and fees
Fattoria Pieve a Salti
A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.
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.
A bedroom with a bed, a sofa, a desk, and a TV. There are windows with curtains and a view of greenery outside.
A historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.

17. Hotel Borgo Antico

Hotel Borgo Antico
Monteroni d'Arbia
United Kingdom
Charles
$101 nightly
$117 total
Oct 20 - Oct 21
Total with taxes and fees
Hotel Borgo Antico
Two people sitting at a round table outdoors with a scenic view of mountains in the background.
A patio area with wicker furniture, a glass table, and a pool in the background.
A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.
A breakfast buffet with various food items and beverages.

18. Hotel Corsignano

Hotel Corsignano
Pienza
United States
shane
$131 nightly
$150 total
Nov 10 - Nov 11
Total with taxes and fees
Hotel Corsignano
A garden pathway leading to a rustic building with a tiled roof, surrounded by lush greenery and red flowers.
An outdoor restaurant with tables and chairs, covered by a wooden roof, and surrounded by greenery.
A modern hotel room with a large window, a bathtub, a seating area, and a view of the outdoors.
A spa setting with a stone wall, a fireplace, and a massage table.

19. Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
San Quirico d'Orcia
United States
Alessio
$124 nightly
$141 total
Nov 2 - Nov 3
Total with taxes and fees
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
A stone building with a courtyard and a canal.
A spacious room with a large bed, two armchairs, a sofa, and a view of the outdoors through a large window.
A bar area with wooden shelves, books, and a brick wall. There are three green bar stools and a patterned rug on the floor.
A bedroom with a wooden ceiling, a bed with a decorative headboard, a bench, and a large wardrobe.

20. Palazzo Brandano

Palazzo Brandano
Trequanda
Canada
Peter
$69 nightly
$79 total
Nov 4 - Nov 5
Total with taxes and fees
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 out? Get away to Castiglione del Bosco!

See all hotels in Castiglione del Bosco
A stone staircase leading to a stone building surrounded by hedges.
Photo by Mario Mürner

Top Castiglione del Bosco Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"La vue est panoramique et le château est grandiose"
Annie 4-night trip
Posted 3 days ago
Castello di Velona Resort Thermal SPA & Winery
Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"Get"
Taisa 1-night trip
Posted 3 days ago
Hotel San Gregorio
Piccolo Hotel Etruria

Piccolo Hotel Etruria

10/10 Excellent
"This is a clean and charming hotel very centrally located in Siena. The morning and afternoon staff were very helpful. We will definitely stay at the Piccolo Hotel Etruria on our next visit. We will also recommend it to friends."
Thomas 1-night trip
Posted 3 days ago
Piccolo Hotel Etruria
L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"Clean room and beautiful Suite. Breakfast was excellent!"
Tracey 2-night trip
Posted 4 days ago
L'Orto delle Terme
Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It was OK for the price. The breakfast was so so, the parking very small and often full. The building is old and was making weird noises occasionally. The location was excellent: just outside LTZ but very close to all the points of interest."
Victor 4-night trip
Posted 4 days ago
Hotel Chiusarelli
Hotel Italia

Hotel Italia

10/10 Excellent
"Staff and hotel was great."
Suzanne 1-night trip
Posted 6 days ago
Hotel Italia
Il Chiostro del Carmine

Il Chiostro del Carmine

10/10 Excellent
"Great breakfast, stunning views of the Tuscan countryside and felt like walking into the past. Exactly as per the photos, a wonderful ambience, full of charm and character. Well located on the edge of the old town, less than 10 minutes walk to the centre. The staff were so friendly and helpful. I would not hesitate to recommend this hotel and hope to come back myself."
Katharine 3-night trip
Posted 9 days ago
Il Chiostro del Carmine
Four Points by Sheraton Siena

Four Points by Sheraton Siena

8/10 Good
"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."
Rajendra 3-night trip
Posted 2 weeks ago
Four Points by Sheraton Siena
Albergo Le Terme

Albergo Le Terme

10/10 Excellent
"It was amazing."
PAUL 3-night trip
Posted 3 weeks ago
Albergo Le Terme

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
$56 nightly
$65 total
Nov 19 - Nov 20
Total with taxes and fees
7.8/10 Good! (259 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
$65 nightly
$75 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (453 reviews)
Piccolo Hotel Etruria
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
$85 nightly
$97 total
Nov 5 - Nov 6
Total with taxes and fees
10/10 Exceptional! (51 reviews)
Torre del Fuggisole
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
$87 nightly
$99 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (113 reviews)
Albergo Centrale
Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
$112 nightly
$128 total
Oct 22 - Oct 23
Total with taxes and fees
9.4/10 Exceptional! (217 reviews)
Hotel La Terrazza di Montepulciano
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

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 Village, which is the heart of the property.The Village is the central hub of Castiglione Del Bosco, offering a collection of restored historic buildings that house the main amenities. You'll find the primary dining options, a well-stocked shop, and a cozy bar here. The village is set amidst rolling hills with vineyards and olive groves stretching in every direction, providing a picturesque backdrop. It's designed for convenience, with everything within a short walk or shuttle ride.For couples seeking a romantic and secluded experience, staying in one of the private villas scattered across the estate is an excellent choice. These villas offer privacy, often with private pools, and stunning views of the Tuscan countryside, while still providing access to all the amenities of The Village. They are well-suited for relaxing and enjoying the quiet surroundings.Families will find the suites and larger accommodations within The Village or nearby ideal. These options often provide more space and easier access to the estate's facilities, including dining and activities.
When is the best time to go to Castiglione Del Bosco?
For an optimal experience in Castiglione Del Bosco, the best times to visit are during the spring (April to June) and fall (September to October) seasons.During spring, the Tuscan countryside awakens with lush greenery and blooming wildflowers, offering pleasant temperatures superb for exploring the vineyards and olive groves. The weather is generally mild and sunny, making it ideal for outdoor activities like hiking, cycling, and enjoying al fresco dining without the intense heat of summer. This period is particularly good for couples seeking picturesque scenery and comfortable conditions for leisurely tours of the region's historic towns.The fall months bring a different kind of beauty, with the landscape transforming into rich hues of gold, red, and brown as the grape harvest begins. This is an exciting time for wine enthusiasts, as many local wineries offer special tours and tastings celebrating the vendemmia. The temperatures remain comfortable, and the crowds tend to be smaller than in the peak summer season, allowing for a more serene experience.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 much is the nightly rate at a Castiglione del Bosco hotel?
Prices for hotels in Castiglione del Bosco often vary, but you can find a great deal from $65 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 the cheapest rate.

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