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

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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.
A villa with a swimming pool, surrounded by lush greenery and a view of distant hills.
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
NT$56,781
NT$62,816 total
includes taxes & fees
Oct 18 - Oct 19
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 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 bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.
A kitchen with a buffet setup, including a variety of food items and glassware.

2. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
United States
Farasley
NT$3,019
NT$4,143 total
includes taxes & fees
Nov 1 - Nov 2
SI Montalcino Hotel
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 dining area with white tables and chairs, a large mirror, and a wine bottle on one table.
A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.

3. Podere Brizio

Podere Brizio
Montalcino
United States
Aseem
NT$6,371
NT$7,294 total
includes taxes & fees
Oct 31 - Nov 1
Podere Brizio
A person relaxing in a hot tub with a view of a vineyard and mountains in the background.
A picnic setup with blankets and cushions on a gravel surface, surrounded by cypress trees and a sunset in the background.
A stone building with a garden and a gazebo.
A pathway flanked by tall, narrow trees leading to a stone building with an arched entrance.

4. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
Canada
Karen
NT$13,718
NT$15,448 total
includes taxes & fees
Nov 5 - Nov 6
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 wine cellar with wooden racks and tables, a sign reading "DROGHERIA," and a rustic ceiling.
A bedroom with a large window overlooking a castle, a bed, and a mirror on the wall.

5. Casa Franci Montalcino

Casa Franci Montalcino
Montalcino
United States
Peter
NT$6,007
NT$6,966 total
includes taxes & fees
Oct 14 - Oct 15
Casa Franci Montalcino
A poolside area with lounge chairs, a table with drinks, and a view of hills.
A room with a large window, a door, and a view of a landscape.
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.

6. Capanna Suites

Capanna Suites
Montalcino
United States
Michael
NT$10,325
NT$11,715 total
includes taxes & fees
Oct 26 - Oct 27
Capanna Suites
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.
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.
A stone building with a swimming pool, white lounge chairs, and a white umbrella.

7. Le Ragnaie

Le Ragnaie
Montalcino
United States
Trevor
NT$3,390
NT$4,086 total
includes taxes & fees
Nov 3 - Nov 4
Le Ragnaie
A pool with a stone wall, a view of the countryside, and a building with a tiled roof.
A buffet setup with various food items, a coffee station, and a counter with beverages.
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.

8. Hotel Dei Capitani

Hotel Dei Capitani
Montalcino
United States
Phillip
NT$4,161
NT$4,864 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Dei Capitani
A logo with a bird and a shield, and the text "AMARAVATI".
A bar area with two people seated at a counter, a glass display case with bottles, and a vase with flowers on the wall.
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.

9. Hotel Ghibellino

Hotel Ghibellino
Buonconvento
Australia
Anna-Maree
NT$2,938
NT$3,339 total
includes taxes & fees
Oct 18 - Oct 19
Hotel Ghibellino
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 stone building with the name "Albergoggiardino" above the entrance. Inside, there is a chandelier, a clock, and a blue chair.
A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.

10. Albergo Giardino

Albergo Giardino
Montalcino
United Kingdom
Norma
NT$2,920
NT$3,499 total
includes taxes & fees
Nov 4 - Nov 5
Albergo Giardino
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 outdoor patio with terracotta-tiled flooring, metal tables and chairs, potted plants, and a view of the sea.
A stone building with a brick archway and a tall cypress tree in front.
An aerial view of a two-story stone building with a swimming pool in the foreground.

11. Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
Montalcino
United States
Roy
NT$4,939
NT$5,718 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Vecchia Oliviera
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 wicker dining table set with breakfast items, a vase of flowers, and a scenic view.
A buffet table with various desserts and a long dining area with tables and chairs.

12. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
NT$2,679
NT$2,947 total
includes taxes & fees
Oct 12 - Oct 13
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 wine tasting room with a marble bar, wine bottles, glasses, wicker furniture, and a view of the sea through a large arched window.
A multi-story building with a central entrance, large windows with shutters, and a paved courtyard.

13. Palazzo Saloni

Palazzo Saloni
Montalcino
United States
Michael
NT$7,325
NT$8,416 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo Saloni
A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.
A landscaped garden with neatly trimmed bushes, a stone pathway, and umbrellas.
A stone house with a covered patio, a stone pathway, and well-maintained landscaping.
A pool surrounded by manicured gardens and vineyards, with a clear view of rolling hills in the background.

14. Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
United States
Gurnek
NT$14,119
NT$15,889 total
includes taxes & fees
Nov 7 - Nov 8
Mastrojanni Relais - Small Luxury Hotels of the World
A stone building with a pool overlooking a mountainous landscape.
A dining area with a table and chairs, a vase with flowers, and a view of the countryside through an arched window.
Vineyard
A stone pathway leading to a gate with tall cypress trees on either side, illuminated by soft lighting.

15. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
Montalcino
NT$18,954
NT$21,207 total
includes taxes & fees
Nov 3 - Nov 4
Castello di Velona Resort Thermal SPA & Winery
A clear pool with a stone wall and a wooden bridge.
An outdoor restaurant with tables and chairs, covered by a wooden roof, and surrounded by greenery.
A narrow cobblestone street with a restaurant named "Trattoria al Vecchio Forno" and a sign indicating "Giardino" (garden).
A stone-walled room with a large bathtub, a fireplace, and a tray with a champagne bottle and glasses.

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

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection
San Quirico d'Orcia
United States
Edward
NT$6,783
NT$7,641 total
includes taxes & fees
Oct 13 - Oct 14
Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection
A bedroom with a bed, a chair, a table, and a stone wall.
An underground wine cellar with brick walls, wooden tables, and chairs.
An outdoor patio with stone walls, a pergola, and a table set for dining.
A piano with sheet music, an easel with a drawing, and a wine bottle in a stone-walled room.

17. Dimora delle Muse

Dimora delle Muse
Montalcino
United States
Bradley N.
NT$5,614
NT$6,462 total
includes taxes & fees
Nov 2 - Nov 3
Dimora delle Muse
A person serving food at a table with various dishes and a wine rack in the background.
A bedroom with a large bed, a wardrobe, a chair, and a ceiling with exposed beams.
A spacious room with a large wooden table, multiple drawers, and a colorful abstract painting on the wall.
A room with a sofa, a checkered rug, a mirror on the wall, and a door leading to another room.

18. Palazzo Lucchini

Palazzo Lucchini
Montalcino
NT$12,600
NT$14,217 total
includes taxes & fees
Oct 19 - Oct 20
Palazzo Lucchini
A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.
A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.
A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.
A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.

19. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
United States
Karen
NT$4,103
NT$4,728 total
includes taxes & fees
Oct 25 - Oct 26
Relais Cloister Pienza
A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.
A woman in a green swimsuit standing in a pool with a stone wall and a glass ceiling.
A breakfast buffet with pastries, bread, and condiments.
A stone building with a view of a courtyard, a pool, and surrounding greenery.

20. L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
United States
Stimson
NT$4,043
NT$4,590 total
includes taxes & fees
Oct 26 - Oct 27
L'Orto delle Terme
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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

Hotel Athena

Hotel Athena

10/10 Excellent
"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"
Hillaine 3-night trip
Posted 3 hours ago
Hotel Athena
Il Chiostro del Carmine

Il Chiostro del Carmine

10/10 Excellent
"This is a wonderful historic property with large bedrooms, large and comfortable but firm beds and spacious common areas. The staff goes out of its way to be accommodating. I would definitely stay again when I am in Siena"
Thomas J. 1-night trip
Posted 22 hours ago
Il Chiostro del Carmine
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
Julia 2-night trip
Posted 1 day ago
Hotel San Gregorio
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 3 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Nice and quiet excellent hospitality"
Mohammed 2-night trip
Posted 3 days ago
Castiglion del Bosco, A Rosewood Hotel
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 5 days ago
Four Points by Sheraton Siena
Albergo Le Terme

Albergo Le Terme

10/10 Excellent
"It was amazing."
PAUL 3-night trip
Posted 9 days ago
Albergo Le Terme
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."
Erick 2-night trip
Posted 12 days ago
Castello di Velona Resort Thermal SPA & Winery
L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"Tout etait parfais. Chambre propre, staff accueillants et disponible au besoin. Petit déjeuner tres bon avec beaucoup de choix de qualité. Location et vue incroyable. Paysage a couper le souffle."
elise 2-night trip
Posted 13 days ago
L'Orto delle Terme

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
NT$1,826
NT$2,116 total
Nov 4 - Nov 5
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
NT$2,462
NT$2,815 total
Nov 4 - Nov 5
includes taxes & fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
NT$2,689
NT$3,065 total
Nov 4 - Nov 5
includes taxes & fees
7.8/10 Good! (451 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
NT$3,025
NT$3,434 total
Nov 3 - Nov 4
includes taxes & fees
8.8/10 Excellent! (111 reviews)
Albergo Centrale
Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
NT$3,572
NT$4,072 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (214 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'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 Grand Hotel Continental Siena – Starhotels Collezione. 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, 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 3395 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 Tenuta Greppo Franco Biondi Santi 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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