Hotels in Montechiaro

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Where to stay in Montechiaro?

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

An interior corridor with arches, columns, and a brick wall.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

1. La Certosa di Pontignano

Castelnuovo Berardenga

$92

$110 total

includes taxes & fees

Oct 25 - Oct 26

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

A stone building with a window and a light fixture.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

2. Agriturismo San Sano

Gaiole in Chianti

$73

$85 total

includes taxes & fees

Oct 21 - Oct 22

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."

3. Four Points by Sheraton Siena

Scacciapensieri

$139

$156 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor patio with tables and chairs, surrounded by potted plants and a red building.

A rustic interior with a fireplace, wooden beams, and a metal rack holding various tools.

A courtyard with brick buildings, a stone wall, and a view of the surrounding town.

A swimming pool with a clear view of the water, a metal structure on the right, and a landscaped area with chairs and plants in the background.

4. Borgo Grondaie

Siena

$83

$95 total

includes taxes & fees

Nov 2 - Nov 3

A table set for breakfast with a scenic view of hills and a cloudy sky.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

5. Palazzo di Valli

Siena

$148

$169 total

includes taxes & fees

Oct 21 - Oct 22

A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.

A bathroom with a sink, mirror, and shower.

6. Sangallo Park Hotel

Vico Alto

$107

$121 total

includes taxes & fees

Nov 2 - Nov 3

A courtyard with a lemon tree, potted plants, and a building with arched windows.

A room with a large window offering a view of a landscaped garden with trees and a pathway.

A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.

A large, historic building with a covered patio and a well-maintained garden.

7. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$190

$215 total

includes taxes & fees

Oct 19 - Oct 20

A hotel room with a bed, bedside tables, a desk with a chair, a television, and a window with curtains.

A modern building with a sign reading 'HOTEL SAN MARCO.'

A buffet counter with various food items including pastries, a pie, and a bowl of eggs.

8. Best Western Hotel San Marco

Siena

$92

$105 total

includes taxes & fees

Nov 2 - Nov 3

A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

A hotel entrance with a sign reading "HOTEL EXPO".

An outdoor dining area with tables and chairs, covered by a canopy, and surrounded by greenery.

A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.

9. Hotel Executive

Scacciapensieri

$91

$103 total

includes taxes & fees

Nov 2 - Nov 3

A table set for dining with a scenic view of rolling hills and distant mountains.

A brick building with a large arched entrance, a metal gate, and a wooden door.

A courtyard with brick buildings, a column, and potted plants.

An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.

10. Castello di Leonina Relais

Asciano

$142

$163 total

includes taxes & fees

Oct 19 - Oct 20

A terrace with multiple sun loungers and a scenic view of green fields and hills.

A spa room with a reception desk, a massage chair, and a window with blinds.

A modern hotel room with a bed, a small table with a hat, a red chair, a window with curtains, and a bathroom with a glass shower enclosure.

A spacious living area with a wooden coffee table, a large potted plant, and a sofa.

11. Precise House Montaperti Siena

Asciano

$83

$98 total

includes taxes & fees

Nov 1 - Nov 2

A grand entrance with a staircase leading to a white building, surrounded by lush greenery and potted plants.

A lobby with a reception desk, a large painting, a potted plant, and a patterned floor.

A swimming pool with a wooden deck, lounge chairs, and umbrellas.

A rooftop terrace with outdoor seating, including a white sofa and wicker chairs, surrounded by potted plants and overlooking a cityscape.

12. Villa Ermellina Siena, a Tribute Portfolio Hotel

Camollia

$168

$188 total

includes taxes & fees

Nov 2 - Nov 3

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone archway leading to a window with a view of tall trees and a distant landscape.

A stone building with a tower, surrounded by people dining at tables with candles.

A historic stone building with a large arched window and a small balcony.

13. Castello di Tornano Wine Resort

Gaiole in Chianti

$142

$165 total

includes taxes & fees

Oct 26 - Oct 27

A modern building with a sign reading "Palace Hotel."

A red building with a reception sign, a bicycle, potted plants, and luggage.

A modern building entrance with a glass door reflecting a parking lot and trees.

A buffet setup with various food items including yogurt cups, fruits, and a bowl of grapes.

14. Palace Hotel Due Ponti

Due Ponti

$78

$89 total

includes taxes & fees

Nov 1 - Nov 2

A hotel entrance with a reception area, glass doors, and a sign above reading "Hotel i Platani".

A hotel reception area with a wooden reception desk, a clock, a fire alarm, and a cityscape painting on the wall.

A hotel lobby with a reception desk, a dining area with tables and chairs, and potted plants.

A hotel room with a bed, a bedside table with a cup and a small plate, a wall-mounted heater, and a window with yellow curtains.

15. Hotel I Platani

Monteriggioni

$68

$81 total

includes taxes & fees

Nov 2 - Nov 3

A pathway lined with trees and a large pot in the center.

A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

A breakfast buffet with pastries and a coffee machine.

16. Villa Montarioso

Montarioso

$80

$94 total

includes taxes & fees

Oct 20 - Oct 21

An outdoor courtyard with a brick wall, potted plants, and a tiled floor.

An outdoor seating area with chairs and a table, overlooking a valley with a view of distant hills and a building.

An aerial view of a historic town with traditional architecture, including a prominent church with a bell tower, surrounded by lush greenery and residential buildings.

A table set for breakfast with croissants, a coffee cup, and a glass of juice.

17. Hotel Santa Caterina

Siena

$104

$117 total

includes taxes & fees

Nov 1 - Nov 2

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

A spacious lobby with white furniture, a coffee station, and a view of the outdoors.

A modern kitchen with dark wooden cabinets, a dining table set with plates, glasses, and cutlery, and a vase of flowers on the right.

A hotel room with a bed, bedside table, and a mirror. There is a small desk with a chair and a vase of flowers. The room has a modern design with a neutral color palette.

18. ApartHotel Anghel

Siena

$67

$79 total

includes taxes & fees

Oct 23 - Oct 24

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

19. Dievole Wine Resort

Castelnuovo Berardenga

$296

$334 total

includes taxes & fees

Oct 28 - Oct 29

A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.

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 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.

20. Hotel Borgo Antico

Monteroni d'Arbia

$95

$110 total

includes taxes & fees

Oct 31 - Nov 1

View all properties

Go beyond your typical stay in Montechiaro

Check out reviews of Montechiaro hotels guests love

La Certosa di Pontignano

Castelnuovo Berardenga

10/10 Exceptional

Jeffrey

Agriturismo San Sano

Gaiole in Chianti

10/10 Exceptional

Angela

Palazzo di Valli

Siena

10/10 Exceptional

We stayed 3 nights at Palazzo di Valli in late April 2022. The property is beautiful and located in a quiet residential area just south of the city's center. It sits on a hill overlooking a valley, and has it's own orchard and flower gardens. Instead of waking up to the sound of motorcycles and delivery trucks under your window, we woke up to chirping birds. Hosts Lorenzo and Giancarlo were wonderful, offering us recommendations, and helping arrange reservations and transportation. It's a bit of...

Joan

Borgo Grondaie

Siena

10/10 Exceptional

tmcmaus

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

10/10 Exceptional

Anonymous traveler

A hotel room with a large bed, a vanity with a mirror, and a green archway.

A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.

A covered outdoor seating area with a pool in the background.

An arched hallway with a marble reception desk, potted plants, and a staircase in the background.

Hotel Certosa Di Maggiano

Siena

10/10 Exceptional

Anonymous traveler

Castello di Leonina Relais

Asciano

10/10 Exceptional

Jennifer

Castello di Tornano Wine Resort

Gaiole in Chianti

10/10 Exceptional

Arwen

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

A table set for breakfast with various dishes, drinks, and a newspaper.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

Hotel Le Fontanelle

Castelnuovo Berardenga

10/10 Exceptional

Anonymous traveler

Sangallo Park Hotel

Vico Alto

10/10 Exceptional

Dirce

Villa Ermellina Siena, a Tribute Portfolio Hotel

Camollia

10/10 Exceptional

Heather

Best Western Hotel San Marco

Siena

10/10 Exceptional

Adriana

Four Points by Sheraton Siena

Scacciapensieri

10/10 Exceptional

Kathryn

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Exceptional

Gary

Hotel Santa Caterina

Siena

10/10 Exceptional

My husband and I stayed at the Santa Caterina for four nights. Normally we like to stay in the center of town, but I booked the Santa Caterina based on its reviews, and I'm so glad I did! The hotel is absolutely charming and it has a beautiful garden with a stunning view of the hills of Tuscany. The front desk staff, especially Lucio, couldn't have done more for us. The breakfast buffet was excellent and in the warmer months, can be eaten in the garden. It's just outside the Porta Romana,...

Ellen

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A person relaxing in a hot tub with a view of a building and trees in the background.

A poolside area with lounge chairs and a view of the night sky.

A rustic stone building with a garden in front.

Belvedere di San Leonino

Castellina in Chianti

10/10 Exceptional

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.

The Club House

Castelnuovo Berardenga

10/10 Exceptional

debbie

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

A stone building with outdoor seating and a garden with roses.

A pool area with lounge chairs and a service person attending to a guest.

Borgo San Felice Resort

Castelnuovo Berardenga

10/10 Exceptional

An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We...

Yael

Hotel Executive

Scacciapensieri

10/10 Exceptional

HENGJUN

A motorcycle parked in front of a brick building with arched doorways and a street lamp.

A room with a desk, a lamp, a television displaying a cityscape, and a plant.

A high-ceilinged room with a large window offering a city view.

A modern bedroom with a bed, bedside table, and a bench.

Torre del Fuggisole

Siena City Centre

10/10 Exceptional

Kristen M