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Our top choices for Montechiaro hotels

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (92 reviews)
"This place is amazing. Wonderful drive to the hotel and the solitude is so great. The breakfast was amazing. Staff was very friendly for our stay. Definitely go back."
Canada
Shawn
The price is CA $162
CA $184 total
includes taxes & fees
Jun 5 - Jun 6
Agriturismo San Sano

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (537 reviews)
"Amazing place just get inside was a pleasure really really q beautiful place to stay Greta views"
United States
Juan
The price is CA $180
CA $211 total
includes taxes & fees
Jun 10 - Jun 11
La Certosa di Pontignano

Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (207 reviews)
"What a lovely stay at a beautiful historic hotel. The grounds are so well kept and peaceful. Dinner was amazing both nights, highly recommend this property. "
Canada
DEANA
The price is CA $236
CA $266 total
includes taxes & fees
Jun 24 - Jun 25
Villa Sabolini

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (138 reviews)
"Excellent hotel, very beautiful, peaceful and serene. Rooms are gorgeous and spacious. Food and service is incredible. Felt very high end and relaxing the whole time! "
United States
Andrew
The price is CA $576
CA $650 total
includes taxes & fees
Jun 21 - Jun 22
Capanna Suites

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.0 out of 10, Wonderful, (108 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
The price is CA $331
CA $376 total
includes taxes & fees
Jun 23 - Jun 24
Castello di Tornano Wine Resort

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (41 reviews)
"Great place to stay and visit all the surrounding hill towns! Breakfast was excellent. Daniela took amazing care of us! Will definitely return!"
United States
Norma
The price is CA $170
CA $195 total
includes taxes & fees
Jun 14 - Jun 15
Hotel Ristorante La Dama nella Vigna

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very good, (60 reviews)
"A little far away from Siena, but buses came by regularly and taxi's only cost about 12 Euros to get you to and from Siena."
United States
Jack
The price is CA $117
CA $137 total
includes taxes & fees
Jun 7 - Jun 8
Palace Hotel Due Ponti

Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
9.6 out of 10, Exceptional, (77 reviews)
"Whole place felt amazing, staff was super! Def recommend!"
United States
Roberto Javier Sanz
The price is CA $243
CA $275 total
includes taxes & fees
Jun 18 - Jun 19
Relais la Costa - Dimora Storica

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (47 reviews)
"Beautiful setting, felt like we were staying in a castle! The beds were comfortable and the property was amazing. Highly recommend this place."
Canada
Heather
The price is CA $104
CA $114 total
includes taxes & fees
Jun 7 - Jun 8
Fondaco del Moro

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
The price is CA $493
CA $552 total
includes taxes & fees
Jun 11 - Jun 12
Fattoria di Vegi

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (212 reviews)
"Very peaceful and staff was very helpful with reservations for excursions"
United States
Giancarlo
The price is CA $287
CA $322 total
includes taxes & fees
Jun 25 - Jun 26
Castello di Fonterutoli Wine Resort

Palazzo di Valli

Palazzo di Valli
3.0 star property
Siena
9.6 out of 10, Exceptional, (424 reviews)
"We had a blast, and the proprietors were fantastic. They had plenty of local knowledge and seemed to have a real passion for what they do. Plus the venue is wonderful, and they have the best patio with views of the Tuscan hills. Would recommend, and would stay again."
United States
John
The price is CA $258
CA $292 total
includes taxes & fees
Jul 4 - Jul 5
Palazzo di Valli

Hotel Borgo Antico

Hotel Borgo Antico
3.0 star property
Monteroni d'Arbia
8.8 out of 10, Excellent, (98 reviews)
"A hidden gem on the Via Francigena. We loved our stay after a day of walking from Siena. Delicious food too. "
United Kingdom
Charles
The price is CA $137
CA $159 total
includes taxes & fees
Jul 3 - Jul 4
Hotel Borgo Antico

Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (192 reviews)
"Beautiful property and very friendly helpful staff"
Canada
Pamela
The price is CA $484
CA $546 total
includes taxes & fees
Jul 2 - Jul 3
Dievole Wine Resort

Locanda Casalta

Locanda Casalta
Strove
The price is CA $184
CA $203 total
includes taxes & fees
Jun 9 - Jun 10
Locanda Casalta

Castello

Castello
3.0 star property
Sovicille
8.6 out of 10, Excellent, (73 reviews)
"Great little place to stay overnight. "
United States
Ivona
The price is CA $121
CA $140 total
includes taxes & fees
Jun 5 - Jun 6
Castello

Il Verreno

Il Verreno
Ambra
9.8 out of 10, Exceptional, (59 reviews)
"I absolutely love this hotel! This is the second year I've stayed here and it's absolutely beautiful, the food is delicious, and the staff is top notch. I highly recommend for anyone who wants to explore beautiful Tuscany."
United States
Marc
The price is CA $360
CA $402 total
includes taxes & fees
Jun 9 - Jun 10
Il Verreno

Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (248 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is CA $113
CA $124 total
includes taxes & fees
Jun 22 - Jun 23
Mercure Petriolo Siena Terme Spa Hotel

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (119 reviews)
"Exquisite villa, it was so hard to leave. I heard about Tuscan hospitality but the staff exceeded any expectation. Peaceful and rejuvenating"
United States
Teodora
The price is CA $140
CA $158 total
includes taxes & fees
Jun 18 - Jun 19
Hotel Colle Etrusco Salivolpi

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (164 reviews)
"Our girls loved having the upstairs to themselves, the staff was friendly and helpful, and the breakfast was *delicious!*"
United States
Michelle
The price is CA $130
CA $175 total
includes taxes & fees
Jun 28 - Jun 29
Hotel Il Viandante
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Top Montechiaro Hotel Reviews

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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 can I save on a Montechiaro hotel booking with Expedia?
Members always get our best prices. Find our best Montechiaro hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 $105 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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