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

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

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

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 rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

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

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

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

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

3. Palazzo di Valli

Siena

$148

$169 total

includes taxes & fees

Oct 21 - Oct 22

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 brick building with three windows, a round blue window, and a sign on the wall.

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

4. Borgo Grondaie

Siena

$83

$95 total

includes taxes & fees

Nov 2 - Nov 3

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 bathroom with a sink, mirror, and shower.

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

5. 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 swimming pool surrounded by lush greenery and a stone pathway.

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

6. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$190

$215 total

includes taxes & fees

Oct 18 - Oct 19

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

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."

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

7. Four Points by Sheraton Siena

Scacciapensieri

$139

$156 total

includes taxes & fees

Nov 2 - Nov 3

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

A historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.

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 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.

8. Hotel Borgo Antico

Monteroni d'Arbia

$95

$110 total

includes taxes & fees

Oct 31 - Nov 1

A conference room with rows of chairs, a projector, a whiteboard, and a podium.

A hotel room with a bed, a wooden headboard, a mirror, and a door.

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

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

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

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

10. Hotel Executive

Scacciapensieri

$91

$103 total

includes taxes & fees

Nov 2 - Nov 3

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

A spacious indoor dining area with wooden ceiling beams, green and pink upholstered chairs, and a central bar area.

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.

11. Villa Ermellina Siena, a Tribute Portfolio Hotel

Camollia

$168

$190 total

includes taxes & fees

Oct 31 - Nov 1

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

A spacious dining area with round tables and wicker chairs, a patterned rug, and a wooden ceiling.

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.

12. 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.

An indoor swimming pool with lounge chairs and a view of the countryside.

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

13. Precise House Montaperti Siena

Asciano

$83

$98 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

14. Castello di Tornano Wine Resort

Gaiole in Chianti

$142

$165 total

includes taxes & fees

Oct 26 - Oct 27

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

A breakfast buffet with pastries and a coffee machine.

A bedroom with a bed, bedside lamps, a wooden table, and a balcony with a view of greenery.

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

15. Villa Montarioso

Montarioso

$79

$93 total

includes taxes & fees

Oct 16 - Oct 17

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

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.

16. Palace Hotel Due Ponti

Due Ponti

$78

$89 total

includes taxes & fees

Nov 1 - Nov 2

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.

A dining area with a wooden table, floral centerpiece, and a view of the garden through the window.

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.

17. Hotel Santa Caterina

Siena

$104

$117 total

includes taxes & fees

Nov 1 - Nov 2

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

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

A room with a view of a forest through a window, a table with a lamp, and a chair.

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

18. Dievole Wine Resort

Castelnuovo Berardenga

$293

$332 total

includes taxes & fees

Oct 28 - Oct 29

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

A modern living room with a sofa, a dining table, and a TV stand.

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.

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

19. ApartHotel Anghel

Siena

$67

$79 total

includes taxes & fees

Oct 12 - Oct 13

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A building with arched windows, a courtyard with a pond, and a metal fence.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

20. Hotel Casafrassi

Castellina in Chianti

$60

$73 total

includes taxes & fees

Oct 4 - Oct 5

View all properties

Go beyond your typical stay in Montechiaro

Check out reviews of Montechiaro hotels guests love

Borgo Grondaie

Siena

10/10 Exceptional

tmcmaus

Sangallo Park Hotel

Vico Alto

10/10 Exceptional

Dirce

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

10/10 Exceptional

Anonymous traveler

Hotel Executive

Scacciapensieri

10/10 Exceptional

HENGJUN

Castello di Tornano Wine Resort

Gaiole in Chianti

10/10 Exceptional

Arwen

Villa Ermellina Siena, a Tribute Portfolio Hotel

Camollia

10/10 Exceptional

Heather

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

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

A dining area with round tables, chairs, chandeliers, and large windows with curtains.

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

Hotel Certosa Di Maggiano

Siena

10/10 Exceptional

Anonymous traveler

Precise House Montaperti Siena

Asciano

10/10 Exceptional

Anonymous traveler

Palace Hotel Due Ponti

Due Ponti

10/10 Exceptional

victor

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

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

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

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

A room with two striped armchairs, a small table with chess pieces, and a mirror reflecting a dining area.

A hallway with wooden flooring, a white door at the end, and a small table with a vase and a statue.

A dining room with a marble table, chairs, and a chandelier. There are framed pictures on the walls and a fireplace.

A bedroom with a large bed, a chandelier, a painting, a dining table with chairs, and a view through a window.

La Dimora Dei Monaci

Siena City Centre

10/10 Exceptional

we stayed for 4 nights and used Seina as our base for our first visit to Tuscany. The owners were very helpful. They provided maps and information on all the local sights, plus some history of the town. One night we asked them to make dinner reservations and they had to call over 10 places due to a busy night. But they found us a great restaurant for dinner. Another day they provide a detailed schedule for buses to visit one of the towns we were interested in. The B&B is very close to the...

Alan

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Exceptional

Gary

An outdoor dining area with wicker chairs, a table set with a bowl of chips, a wine glass, and a menu.

A hotel room with a bed, two chairs, a window with a view of a cityscape, and a radiator.

A building with a red and white facade, a balcony with a blue flag, and a red awning over the entrance.

A building with a pink awning and a garden with red and white flowers.

Villa Elda Boutique Hotel

San Prospero

10/10 Exceptional

We enjoyed our recent stay at Hotel Villa Elda on our recent honeymoon in Tuscany. This small hotel is located a short walk (perhaps 10 minutes) from the historic center of Siena. We found the staff, including Riccardo and Sara, to be very helpful and pleasant during our stay. Riccardo provided excellent recommendations for meals, and Sara gave us easy and accurate directions to the next stop on our trip, as we headed towards the coast and the island of Elba. Thank you again! The hotel is...

Nick

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

Hotel Borgo San Luigi

Monteriggioni

10/10 Exceptional

James

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

A hotel room with a bed, a desk, a chair, a window with curtains, a lamp, and a view of the landscape.

A courtyard with wicker furniture, a building with multiple windows and arches, and well-maintained greenery.

A dining area with checkered flooring, tables set with white tablecloths, and wicker chairs.

Palazzo Ravizza

Siena Historical Center

10/10 Exceptional

Anonymous traveler

A bathroom with a window view of a historic building and a tiled roof.

A bedroom with a large bed, a mirror, and a painting on the wall.

A modern living room with a sofa, a wooden dining table with chairs, a glass door leading outside, and a wall with floral artwork.

An outdoor patio with tables and chairs, surrounded by planters and umbrellas.

Siena Vip

Siena City Centre

10/10 Exceptional

Geoffrey

A pool with clear water and a row of white lounge chairs facing a scenic hillside view.

A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.

A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

Palazzo Squarcialupi

Castellina in Chianti

10/10 Exceptional

Jacqueline

A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.

A bench in a park with a lamp post and a building in the background.

A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.

A hallway with a wooden altar, benches, and a carpet with a floral pattern.

Villa Casalecchi Country Hotel

Castellina in Chianti

10/10 Exceptional

George H

A brick building with two arched windows, one with a metal grill and the other with a decorative glass design.

A modern bedroom with a large bed, a built-in vanity with a mirror, and a bedside lamp.

A historic building with arched ceilings, brick walls, and a staircase leading to an upper level. Tables and chairs are arranged in the lower area, and there are decorative shields on the ceiling.

A narrow, stone-walled stairwell with a small, enclosed area at the bottom featuring a desk and a chair.

Hotel Palazzetto Rosso

Siena City Centre

10/10 Exceptional

Chad

Frequently Asked Questions

What hotels do travelers like in Montechiaro?

Guests like Hotel Athena, La Certosa di Pontignano and Grand Hotel Continental Siena – Starhotels Collezione.

Can I book a refundable hotel in Montechiaro?

If you want the flexibility to change your plans to Montechiaro, most properties offer refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Montechiaro be like during my vacation?

The warmest months in Montechiaro are usually August and July with an average temp of 72°F. January and February are the chilliest months when the average temp is 44°F. The rainiest months are November and October.

Why should I book my Montechiaro hotel with Hotels.com?

There are plenty of reasons to book your Montechiaro travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.