Rolling hills, vineyards, and distant mountains.

Vacation homes in Montalcino

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Vacation homes in Montalcino

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a vacation rental stay in Montalcino on Hotels.com. These Montalcino vacation rentals consistently deliver on quality, location and traveler experience. Last updated on September 11, 2026.

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 view through a window with a natural landscape, including hills and a river.

1. Corte Francigena - Apartments

Montalcino

CNY1,129

CNY1,320 total

includes taxes & fees

Oct 12 - Oct 13

An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

A dining table with a view of a green field through an arched window, a vase with flowers, and a tray with food and drinks.

A swimming pool with a clear view of the surrounding forest and hills.

A table set with a bottle of wine, glasses, and a plate of food, overlooking a mountainous landscape.

2. Bosco della Spina

Murlo

CNY754

CNY892 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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.

3. Palazzo Saloni

Montalcino

CNY2,394

CNY2,711 total

includes taxes & fees

Sep 13 - Sep 14

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

A building with a symmetrical facade, a central entrance, and a fountain in the courtyard.

A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

4. Hotel San Gregorio

Pienza

CNY1,326

CNY1,505 total

includes taxes & fees

Oct 10 - Oct 11

A poolside area with two glasses of water, candles, and a stone pathway.

A bedroom with a bed, a nightstand, a lamp, a painting, and a view through a window.

A courtyard with a stone pathway, potted plants, and a building with multiple windows and a tiled roof.

A breakfast table with orange juice, pastries, and a view of rolling hills in the background.

5. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

CNY1,186

CNY1,336 total

includes taxes & fees

Sep 16 - Sep 17

An arched doorway leading to a building with a wooden door and a staircase.

A cozy living room with a fireplace, comfortable seating, and a decorative mirror.

A balcony with a view of a town, including a church tower and distant mountains.

A rustic room with a stone floor, wooden beams, a fireplace, and shelves with various items.

6. Residenza Fabroni

Montepulciano

CNY616

CNY709 total

includes taxes & fees

Sep 23 - Sep 24

A historic building with a tower, a courtyard, and a well-lit entrance.

A courtyard with brick arches, potted plants, and outdoor seating.

A spacious room with a pool table, a sofa, and a grand piano.

A stone building with a gravel driveway, surrounded by trees and a well-maintained garden.

7. Abbadia Sicille Relais

Trequanda

CNY944

CNY1,061 total

includes taxes & fees

Oct 4 - Oct 5

A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

A spacious living room with a wooden ceiling, a dining table with chairs, a piano, and a large window.

A bedroom with a large bed, wooden flooring, a staircase, and a bathroom with a mirror and sink.

A window with a view of a green landscape and hills.

8. Il Tosco

Montepulciano

CNY2,189

CNY2,439 total

includes taxes & fees

Sep 24 - Sep 25

9. montorio

Montepulciano

CNY784

CNY894 total

includes taxes & fees

Oct 3 - Oct 4

A terrace with a table set for breakfast, overlooking a scenic landscape.

A buffet table with pastries, fruits, and drinks, a bust sculpture labeled 'DANTE', and a wooden cabinet with drawers.

A bedroom with a large bed, a desk, two chairs, and a window with a view of a clock tower.

A room with a fireplace, seating area, and a decorative ceiling.

10. Delcorto Suites

Montepulciano

CNY1,327

CNY1,491 total

includes taxes & fees

Oct 6 - Oct 7

A stone archway leading to a building entrance with a wooden door.

A hotel room with a bed, a nightstand, a window with curtains, a radiator, and a wall-mounted picture.

A courtyard with stone flooring, arches, and potted plants.

An interior courtyard with multiple arches and a high ceiling.

11. Bellarmino Boutique Apartments

Montepulciano

CNY473

CNY551 total

includes taxes & fees

Oct 4 - Oct 5

A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

A rustic wooden door with a stone wall and lush greenery.

An arched doorway surrounded by dense foliage.

A cozy living room with a fireplace, a chandelier, and a wooden door.

12. Borgo Lucignanello Bandini

Montalcino

CNY2,444

CNY2,767 total

includes taxes & fees

Oct 1 - Oct 2

A terrace with a table and chairs, a view of the countryside, and a stone wall.

A bar with shelves of wine bottles and glasses on a table.

A wine cellar with a long table set for dining, surrounded by wine racks and shelves.

A living room with a fireplace, a sofa, and a view of the sea through arched windows.

13. Osteria del Borgo

Montepulciano

A stone building with a wooden door, a staircase, and a small window with a metal grill.

A kitchen with a dining table set for two, a gas stove, and a potted plant on the wall.

A narrow street with buildings on either side, featuring balconies and potted plants.

A staircase with a handrail leading to a door with a blue handle.

14. Casa Gioia - Casa Olivieri

Pienza

CNY789

CNY899 total

includes taxes & fees

Oct 12 - Oct 13

A person in a swimming pool with a view of trees and distant hills.

A spacious dining area with a wooden table and chairs, a large wall clock, and a view through a window.

A stone staircase leading to a wooden door, with a brick wall and a window with green shutters.

A spacious living room with a high ceiling, a sofa set, a round coffee table, and a fireplace.

15. Albergo Diffuso Borgo Santo

Asciano

CNY1,714

CNY1,925 total

includes taxes & fees

Oct 12 - Oct 13

A pool area with lounge chairs, a building with a staircase, and a clear sky.

A building entrance with a wooden door, a large potted plant, and a stone wall.

A bedroom with a bed, a window with curtains, a radiator, and a wardrobe.

A room with a wooden table, a chair, a bottle, and a glass. There is a window with curtains, and a view of greenery outside.

16. Poggio delle Rose Tuscany Relais

Chianciano Terme

A villa with a swimming pool, large windows, and a view of the countryside.

A spacious restaurant with wooden tables and chairs, a stone wall with wine bottles, and a large window.

A building entrance with a door labeled 'Residence del Morgo,' a stone bench, and potted plants.

A balcony with a view of a countryside landscape, a tall cypress tree, and a table with chairs.

17. Tuscanflat Castle

Toscana

A cave-like interior with a water feature and a seating area.

A modern bathroom with a large mirror, a wooden vanity, and a glass shower enclosure.

A spa area with a hot tub and a small pool, surrounded by stone walls and a wooden bench.

An aerial view of a villa complex with multiple buildings, a swimming pool, and surrounding vineyards.

18. Casanova - Family Apartments Residence

San Quirico d'Orcia

A coastal town with a historic tower, a swimming pool, and lush greenery.

A courtyard with outdoor seating, bicycles, and a garden with white and red flowers.

A well-lit urban street at dusk with a park, benches, and a mountain in the background.

A dome-shaped tent with a kitchen area, white chairs, and a table.

19. Parco delle Piscine - Campground

Sarteano

A rectangular pool with a surrounding deck, lounge chairs, and a stone wall.

A bedroom with a four-poster bed, framed photographs on the wall, and a window with curtains.

A spacious living room with a large sofa, a coffee table, and a fireplace. There is a bookshelf and a dining table in the background.

A pathway flanked by tall trees and potted plants.

20. Antico Brunello

Montalcino

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Top landmarks in Montalcino

Castello Banfi

9.4/10 (51 reviews)

Travelers might want a tour of Castello Banfi, just one of the places to visit in the heart of Poggio alle Mura.

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Fortress of Montalcino

9.2/10 (54 reviews)

If you're planning a bit of sightseeing during your trip, head to Fortress of Montalcino— just one of the monuments in central Montalcino.

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Tenuta Greppo Franco Biondi Santi

8.6/10 (8 reviews)

Travelers might want a tour of Tenuta Greppo Franco Biondi Santi, just one of the places to visit, and located 1 mi (1.6 km) from central Montalcino.

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Abbazia di Sant'Antimo

9.6/10 (111 reviews)

If you're planning a bit of sightseeing during your trip, head to Abbazia di Sant'Antimo— just one of the landmarks located 4 mi (6.5 km) from central Montalcino.

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Castiglion del Bosco Winery

9.6/10 (5 reviews)

Travelers might want a tour of Castiglion del Bosco Winery, just one of the places to visit in the heart of Castiglione del Bosco.

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Poggio Antico

9.6/10 (7 reviews)

Travelers might want a tour of Poggio Antico, just one of the places to visit, and located 2.7 mi (4.3 km) from central Montalcino.

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Torrenieri Montalcino Station

9.0/10 (2 reviews)

Torrenieri Montalcino Station is 0.4 mi (0.6 km) from central Torrenieri, why not stop by during your stay.

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Capanna of Cencioni

10.0/10 (10 reviews)

Travelers might want a tour of Capanna of Cencioni, just one of the places to visit, and located 1.2 mi (1.9 km) from central Montalcino.

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Learn more about Montalcino

Montalcino, well-known for its wineries and castle, features attractions such as Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi. This historical city has something for everyone including sights like Abbazia di Sant'Antimo and Castiglion del Bosco Winery within a rural setting.

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A wooden sign with grape illustrations and the text "Grapho blu" against a backdrop of a historic building and a scenic view.

About the destination

Spend time appreciating the historic sites, and checking out the wine tasting in Montalcino. Simply book a local tour to enjoy your stay a little more. Plan a fun excursion to Tenuta Greppo Franco Biondi Santi and Castiglion del Bosco Winery while here. You might find that sights like Fortress of Montalcino and Abbazia di Sant'Antimo are worth a visit.

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