⭐ Top 10 Hotels Near Castiglion del Bosco Winery for 2026

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

Tomorrow

This weekend

Next weekend

Our top choices for Castiglion del Bosco Winery hotels

An infinity pool with lounge chairs and umbrellas, surrounded by a forested hillside.

A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.

A rural landscape with a stone house, a swimming pool, and rolling hills in the background.

An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.

1. Castiglion del Bosco, A Rosewood Hotel

0.5 km from Castiglion del Bosco Winery

Mohammed

S$1,794

includes taxes & fees

4 Nov - 5 Nov

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 large bed, a bedside table, a lamp, a window with curtains, and a view of greenery outside.

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.

2. SI Montalcino Hotel

6.8 km from Castiglion del Bosco Winery

Farasley

S$160

includes taxes & fees

5 Nov - 6 Nov

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

A stone building with a garden and a gazebo.

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.

3. Villa Le Prata - Residenza del Vescovo

6.1 km from Castiglion del Bosco Winery

Karen

S$627

includes taxes & fees

4 Nov - 5 Nov

A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

A stone building with multiple windows, a balcony, and a scenic view of rolling hills and mountains.

A row of sun loungers with umbrellas, set against a stone wall and a gravel path, overlooking a hilly landscape.

A stone wall with a metal railing and a view of a hilly landscape.

4. Corte Francigena - Apartments

12.7 km from Castiglion del Bosco Winery

Ivan

S$172

includes taxes & fees

1 Nov - 2 Nov

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.

A piano with sheet music, an easel with a drawing, and a wine bottle in a stone-walled room.

An underground wine cellar with brick walls, wooden tables, and chairs.

5. Dimora delle Muse

10.2 km from Castiglion del Bosco Winery

Bradley N.

S$256

includes taxes & fees

2 Nov - 3 Nov

A poolside area with two lounge chairs and a woven ottoman.

A view through a window with a stone wall and gravel ground, overlooking a landscape with fields and distant hills.

A garden with red flowers, a pool area with lounge chairs, and a stone wall.

A bedroom with a large bed, a red sofa, a wooden wardrobe, and a view through a glass door.

6. Il Burellino Wine & Resort

5.6 km from Castiglion del Bosco Winery

Timothy

S$248

includes taxes & fees

15 Nov - 16 Nov

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 brick-walled bar with wooden shelves stocked with bottles, tables, and chairs.

A bedroom with a large window overlooking a castle, a bed, and a mirror on the wall.

7. Casa Franci Montalcino

6.5 km from Castiglion del Bosco Winery

Jim

S$333

includes taxes & fees

15 Nov - 16 Nov

A stone building with a tiled roof, a paved pathway, and a well-maintained garden.

A stone building with a wooden deck and white lounge chairs.

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.

8. Podere Brizio

6.5 km from Castiglion del Bosco Winery

Aseem

S$284

includes taxes & fees

16 Nov - 17 Nov

A pool with lounge chairs and a sunset view.

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.

9. Mercure Petriolo Siena Terme Spa Hotel

9.7 km from Castiglion del Bosco Winery

Mike

S$121

includes taxes & fees

25 Oct - 26 Oct

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

A buffet with various food items and condiments.

A historic town with terracotta-tiled buildings, stone arches, and a cobblestone street.

A bedroom with a bed, a desk, a chair, a window with a view, and a wall clock.

10. B&B Le Scalette di Piazza

6.5 km from Castiglion del Bosco Winery

François

S$173

includes taxes & fees

27 Oct - 28 Oct

A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

A multi-story building with a central entrance, large windows with shutters, and a paved courtyard.

A wine tasting room with a marble bar, wine bottles, glasses, wicker furniture, and a view of the sea through a large arched window.

11. Palazzo Saloni

6.7 km from Castiglion del Bosco Winery

Michael

S$409

includes taxes & fees

1 Nov - 2 Nov

A stone building with a courtyard, featuring a central archway and a tiled roof.

A swimming pool at dusk with clear reflections, surrounded by trees and lounge chairs.

A rustic entrance with a metal gate, brick walls, and a stone archway leading to a courtyard.

A rustic interior with a central fireplace, wooden beams, stone walls, and a dining area with tables.

12. Il Canto del Sole

17.8 km from Castiglion del Bosco Winery

Corinna

S$185

includes taxes & fees

27 Oct - 28 Oct

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 stone building with a tiled roof, surrounded by a grassy area and flowering plants.

13. Agriturismo Il Macchione

19.7 km from Castiglion del Bosco Winery

YOUNG BAE

S$217

includes taxes & fees

5 Nov - 6 Nov

A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

A rustic stone building with a tiled roof, a covered patio with outdoor seating, and well-maintained gardens.

A covered outdoor seating area with stone pillars, a table, and chairs.

A historic building with a stone facade, surrounded by a well-maintained garden with yellow flowers and tall trees.

14. Antico Casale L'Impostino

10.9 km from Castiglion del Bosco Winery

Maria

S$184

includes taxes & fees

25 Oct - 26 Oct

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.

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.

15. Capanna Suites

6.8 km from Castiglion del Bosco Winery

Randy

S$425

includes taxes & fees

31 Oct - 1 Nov

A bedroom with a wooden bed, an arched stone wall, and two wall-mounted lights.

A swimming pool with lounge chairs and a house in the background.

A stone building with a courtyard, outdoor seating, and a warm light setting.

A stone building with a staircase leading to the entrance, outdoor seating, and a well-lit patio area.

16. Sarna Residence

15.3 km from Castiglion del Bosco Winery

Bokang

S$173

includes taxes & fees

2 Nov - 3 Nov

A rustic villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.

A rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.

A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.

An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.

17. Podere Spedalone

18.8 km from Castiglion del Bosco Winery

Sana

S$222

includes taxes & fees

30 Oct - 31 Oct

A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

A pool surrounded by manicured gardens and vineyards, with a clear view of rolling hills in the background.

A stone house with a covered patio, a stone pathway, and well-maintained landscaping.

A landscaped garden with neatly trimmed bushes, a stone pathway, and umbrellas.

18. Mastrojanni Relais - Small Luxury Hotels of the World

13 km from Castiglion del Bosco Winery

Gurnek

S$579

includes taxes & fees

24 Oct - 25 Oct

A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

An outdoor patio with stone walls, green cushioned seating, a table with chairs, and a decorative umbrella.

A spacious living area with leather armchairs, a wooden cabinet with glass doors, and a red carpet.

A stone building with a swimming pool, white lounge chairs, and a white umbrella.

19. Le Ragnaie

7.4 km from Castiglion del Bosco Winery

Trevor

S$156

includes taxes & fees

10 Nov - 11 Nov

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.

An aerial view of a property with a main building, a swimming pool, and surrounding green fields.

20. Fattoria Pieve a Salti

11.1 km from Castiglion del Bosco Winery

Marko

S$165

includes taxes & fees

10 Nov - 11 Nov

View all properties

Hotels recommended for families near Castiglion del Bosco Winery

Castiglion del Bosco, A Rosewood Hotel

Montalcino

S$1,794

includes taxes & fees

4 Nov - 5 Nov

Casa Franci Montalcino

Montalcino

S$333

includes taxes & fees

15 Nov - 16 Nov

Palazzo Saloni

Montalcino

S$409

includes taxes & fees

1 Nov - 2 Nov

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

A narrow hallway with wooden doors on either side, leading to a room with a tiled floor and a window with curtains.

A spacious kitchen with wooden beams, a dining table with chairs, and a wooden cabinet.

A bedroom with a bed, a nightstand, a lamp, a curtain, and a wooden door with a sign.

Idolina Guest House

Montalcino

S$140

includes taxes & fees

14 Nov - 15 Nov

A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.

An arched stone doorway leading to a covered outdoor seating area with a table and benches.

A stone building with a courtyard, large potted plants, and a well-maintained lawn.

A cozy interior with a dining area, a sofa, and a kitchen.

Colsereno Boutique Wine Hotel resort

Montalcino

S$309

includes taxes & fees

2 Nov - 3 Nov

A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.

A rustic interior with stone walls, a large ornate mirror, a blue sofa, and a wooden coffee table.

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.

Albergo Giardino

Montalcino

S$177

includes taxes & fees

23 Nov - 24 Nov

B&B Le Scalette di Piazza

Montalcino

S$173

includes taxes & fees

27 Oct - 28 Oct

A pool with a stone wall, a view of the countryside, and a building with a tiled roof.

A terrace with outdoor seating, a view of the landscape, and a building with large windows.

A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.

Hotel Dei Capitani

Montalcino

S$191

includes taxes & fees

28 Oct - 29 Oct