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Oct 24 - Oct 25
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Oct 25 - Oct 26
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Our top choices for Montechiaro hotels

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

1. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
United States
Rodolfo
CA $133
CA $159 total
includes taxes & fees
Nov 16 - Nov 17
La Certosa di Pontignano - Place of Charme
A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.
A modern living room with a glass coffee table, white sofas, and decorative plants.
A hotel entrance with a sign reading "HOTEL EXPO".
A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.

2. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Andras
CA $92
CA $105 total
includes taxes & fees
Nov 23 - Nov 24
Hotel Executive
A table set for breakfast with a scenic view of hills and a cloudy sky.
A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.
A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.
An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

3. Palazzo di Valli

Palazzo di Valli
Siena
United States
Luanne
CA $151
CA $171 total
includes taxes & fees
Nov 21 - Nov 22
Palazzo di Valli
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 swimming pool surrounded by lush greenery and a stone pathway.

4. Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Canada
Anita
CA $167
CA $191 total
includes taxes & fees
Oct 25 - Oct 26
Villa Scacciapensieri Boutique Hotel
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 reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

5. Four Points by Sheraton Siena

Four Points by Sheraton Siena
Scacciapensieri
United States
Ralph
CA $183
CA $206 total
includes taxes & fees
Nov 7 - Nov 8
Four Points by Sheraton Siena
An outdoor patio with tables and chairs, surrounded by potted plants and a red building.
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.
A brick building with three windows, a round blue window, and a sign on the wall.
A rustic interior with a fireplace, wooden beams, and a metal rack holding various tools.

6. Borgo Grondaie

Borgo Grondaie
Siena
United Kingdom
Simon
CA $106
CA $122 total
includes taxes & fees
Nov 8 - Nov 9
Borgo Grondaie
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 rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

7. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
Australia
Glen
CA $94
CA $109 total
includes taxes & fees
Oct 30 - Oct 31
Agriturismo San Sano
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 hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.
A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.

8. Sangallo Park Hotel

Sangallo Park Hotel
Vico Alto
United Kingdom
Marcio Tadeu
CA $122
CA $142 total
includes taxes & fees
Oct 25 - Oct 26
Sangallo Park Hotel
Interior
A modern hotel lobby with glass-top tables, a magazine, and a small plant.
A modern building with a sign reading 'HOTEL SAN MARCO.'
A hotel room with a bed, a wooden headboard, a mirror, and a door.

9. Best Western Hotel San Marco

Best Western Hotel San Marco
Siena
United Kingdom
C.K.
CA $129
CA $147 total
includes taxes & fees
Nov 4 - Nov 5
Best Western Hotel San Marco
A villa with a swimming pool, outdoor seating, and a tennis court.
A hotel room with a bed, a nightstand, a lamp, and a view of a landscape through a window.
A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.
A pool area with lounge chairs and umbrellas, a stone planter with flowers, and a building with balconies in the background.

10. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
United States
Deanna
CA $187
CA $212 total
includes taxes & fees
Oct 25 - Oct 26
Villa Curina Resort
A grand entrance with a staircase leading to a white building, surrounded by lush greenery and potted plants.
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.
A lobby with a reception desk, a large painting, a potted plant, and a patterned floor.

11. Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel
Camollia
Sweden
Sebastian
CA $195
CA $220 total
includes taxes & fees
Nov 24 - Nov 25
Villa Ermellina Siena, a Tribute Portfolio Hotel
A table set for dining with a scenic view of rolling hills and distant mountains.
An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.
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.

12. Castello di Leonina Relais

Castello di Leonina Relais
Asciano
United States
Brooke
CA $159
CA $184 total
includes taxes & fees
Oct 25 - Oct 26
Castello di Leonina Relais
A pathway lined with trees and a large pot in the center.
A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.
A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.
A breakfast buffet with pastries and a coffee machine.

13. Villa Montarioso

Villa Montarioso
Montarioso
Canada
Michael
CA $106
CA $125 total
includes taxes & fees
Nov 15 - Nov 16
Villa Montarioso
The entrance to a hotel with a sign reading "HOTEL ITALIA". There are two receptionists standing at the reception desk.
A breakfast buffet with various food items, a coffee station, and a large mirror on the wall.
A hotel room with a bed, a TV, a dining area with a table and chairs, and a view of the outside.
A bar area with a white countertop, clear chairs, and shelves of liquor bottles.

14. Hotel Italia

Hotel Italia
Camollia
United States
Shaji
CA $95
CA $110 total
includes taxes & fees
Nov 24 - Nov 25
Hotel Italia
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.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A historic stone building with a large arched window and a small balcony.

15. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Karina
CA $213
CA $247 total
includes taxes & fees
Oct 27 - Oct 28
Castello di Tornano Wine Resort
A hotel room with a large bed, a vanity with a mirror, and a green archway.
An outdoor dining area with tables and chairs, potted plants, and a tiled floor.
An arched hallway with a marble reception desk, potted plants, and a staircase in the background.
A view of a courtyard with a large tree, outdoor seating, and a building in the background.

16. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
CA $396
CA $445 total
includes taxes & fees
Nov 24 - Nov 25
Hotel Certosa Di Maggiano
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 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 modern living room with a sofa, a dining table, and a TV stand.

17. ApartHotel Anghel

ApartHotel Anghel
Siena
United States
jon
CA $81
CA $96 total
includes taxes & fees
Nov 15 - Nov 16
ApartHotel Anghel
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 room with a glass table, a vase with flowers, a bottle of wine, 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

Dievole Wine Resort
Castelnuovo Berardenga
Norway
Magdalena
CA $358
CA $407 total
includes taxes & fees
Nov 16 - Nov 17
Dievole Wine Resort
An outdoor courtyard with a brick wall, potted plants, and a tiled floor.
A table set for breakfast with croissants, a coffee cup, and a glass of juice.
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.

19. Hotel Santa Caterina

Hotel Santa Caterina
Siena
United States
Brian
CA $154
CA $174 total
includes taxes & fees
Nov 24 - Nov 25
Hotel Santa Caterina
A terrace with multiple sun loungers and a scenic view of green fields and hills.
A spacious living area with a wooden coffee table, a large potted plant, and a sofa.
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.

20. Precise House Montaperti Siena

Precise House Montaperti Siena
Asciano
Canada
Dieter
CA $121
CA $143 total
includes taxes & fees
Nov 24 - Nov 25
Precise House Montaperti Siena
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Top Montechiaro Hotel Reviews

NH Siena

NH Siena

10/10 Excellent
"The room isn't cleaned too well. There were some crumbs that were attracting ants. Other than that- no issues"
Rakhshan 1-night trip
Posted 21 hours ago
NH Siena
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."
mauricio 2-night trip
Posted 1 day ago
Castiglion del Bosco, A Rosewood Hotel
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good
"Excellent location. Very nice service."
mauricio 1-night trip
Posted 1 day ago
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Minerva

Hotel Minerva

10/10 Excellent
"The check-in staff were very friendly, helpful, and spoke English. The €20 parking in their garage was very nice and convenient, especially when it rained. Nice view from the room."
Greg 1-night trip
Posted 2 days ago
Hotel Minerva
Il Chiostro del Carmine

Il Chiostro del Carmine

8/10 Good
"Breakfast"
Joseph 1-night trip
Posted 3 days ago
Il Chiostro del Carmine
Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."
Kurt 1-night trip
Posted 4 days ago
Hotel Italia
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Great location amazing place"
Rodolfo 1-night trip
Posted 4 days ago
La Certosa di Pontignano
Piccolo Hotel Etruria

Piccolo Hotel Etruria

10/10 Excellent
"This is a clean and charming hotel very centrally located in Siena. The morning and afternoon staff were very helpful. We will definitely stay at the Piccolo Hotel Etruria on our next visit. We will also recommend it to friends."
Thomas 1-night trip
Posted 8 days ago
Piccolo Hotel Etruria
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 13 days ago
Castello di Spaltenna- Small Luxury Hotels of the World

More cheap stays in Montechiaro

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
CA $75
CA $87 total
Nov 24 - Nov 25
includes taxes & fees
7.8/10 Good! (259 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
CA $101
CA $116 total
Nov 24 - Nov 25
includes taxes & fees
7.8/10 Good! (453 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
CA $110
CA $125 total
Nov 4 - Nov 5
includes taxes & fees
8.8/10 Excellent! (114 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
CA $123
CA $140 total
Nov 4 - Nov 5
includes taxes & fees
10/10 Exceptional! (52 reviews)
Torre del Fuggisole
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence
La Locanda di Casalmustia

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI
Get rates
8.6/10 Excellent! (44 reviews)
La Locanda di Casalmustia

Frequently asked questions

What is the best area to stay in Montechiaro?
The best area to stay in Montechiaro for a classic Tuscan experience is within the Montechiaro Estate itself, particularly around the historic Villa and its immediate surroundings.The Montechiaro Estate is a sprawling property that encompasses vineyards, olive groves, and the beautifully restored Villa. Staying here means you're right in the heart of the Chianti Classico region, with stunning views of the rolling hills and easy access to the estate's wine production facilities. The main area around the Villa offers a sense of tranquillity and exclusivity.Couples looking for a romantic escape will find the Montechiaro Estate ideal. You'll be surrounded by picturesque landscapes, superb for leisurely walks among the vines. The estate often hosts wine tastings and culinary experiences, providing a sophisticated and intimate way to explore Tuscan culture and cuisine.
When is the best time to go to Montechiaro?
The best time to go to Montechiaro is during the spring (April to May) and autumn (September to October) months.These periods offer pleasant weather, ideal for exploring the Tuscan countryside without the intense heat of summer or the cooler, sometimes rainy, conditions of winter. You'll find the landscape at its most picturesque, with rolling hills vibrant green in spring and rich with autumnal colours later in the year.For couples looking for a romantic getaway, these shoulder seasons provide a more tranquil experience. You can enjoy wine tastings at local vineyards, leisurely walks through olive groves, and dining al fresco in the evenings, all without the larger crowds often seen in peak summer. The mild temperatures are great for exploring the smaller hilltop towns nearby.Travellers interested in culinary experiences will also find these months rewarding. Spring brings fresh local produce, while autumn is harvest season, offering opportunities to participate in grape harvesting or truffle hunting, followed by delicious, seasonal meals.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Montechiaro.
How much is the nightly rate at a Montechiaro hotel?
Prices for hotels in Montechiaro often vary, but you can find a great deal from CA $76 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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