Montechiaro Vacation Rentals

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Our top choices for Montechiaro vacation rentals

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is CA $2,128
CA $2,348 total
includes taxes & fees
Apr 24 - Apr 25
Terre di Baccio

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is CA $141
CA $161 total
includes taxes & fees
Apr 20 - Apr 21
Il Pozzo di Sant'Andrea

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is CA $222
CA $258 total
includes taxes & fees
Apr 28 - Apr 29
Villa Curina Resort

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (29 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is CA $212
CA $234 total
includes taxes & fees
May 16 - May 17
Villa di Sotto

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is CA $208
CA $343 total
includes taxes & fees
May 13 - May 14
Borgo Il Poggiaccio

Villa Cristina

Villa Cristina
Castellina in Chianti
7.8 out of 10, Good, (39 reviews)
"Arnaque absolue par rapport aux photos. Sdb salle moisi partout, wc jaune de calcaire. Aucune isolation phonique. Photos ne correspondent pas Chambre dans garage hauteur sous planfond nulle obligé de se baisser."
France
pascal
Villa Cristina

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is CA $244
CA $273 total
includes taxes & fees
Apr 20 - Apr 21
Antico Borgo Poggiarello

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Great time, perfect property and location."
United States
Christopher
The price is CA $335
CA $375 total
includes taxes & fees
Apr 20 - Apr 21
Ca' Bianca Tuscany Relais

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is CA $71
CA $82 total
includes taxes & fees
May 17 - May 18
Sportland

A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
8.0 out of 10, Very good, (26 reviews)
"Pleasant place"
France
Claude
The price is CA $189
CA $214 total
includes taxes & fees
May 19 - May 20
A Casa Mastacchi

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (434 reviews)
"Nice place!"
United States
Pavel
The price is CA $199
CA $225 total
includes taxes & fees
Apr 22 - Apr 23
Siena Vip

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (202 reviews)
"Room was excellent, location was perfect for seeing Siena and restaurant was also excellent"
United Kingdom
John
The price is CA $165
CA $188 total
includes taxes & fees
May 14 - May 15
Il Battistero Siena - Residenza d'Epoca

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is CA $152
CA $172 total
includes taxes & fees
Apr 19 - Apr 20
Casa di Campagna in Toscana

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is CA $283
CA $315 total
includes taxes & fees
May 13 - May 14
Riserva di Fizzano Residence

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is CA $185
CA $209 total
includes taxes & fees
Apr 19 - Apr 20
La Coroncina Lodging

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (170 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is CA $125
CA $151 total
includes taxes & fees
Apr 20 - Apr 21
Bosco della Spina

Porta Pispini Residence

Porta Pispini Residence
2.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (22 reviews)
"Parking is easy and very close to the south entrance of old town. Room is same as described. Well arranged and cozy. Very kind staffs. Kitchen, washing machine and dishwasher are useful."
Australia
Won
The price is CA $145
CA $165 total
includes taxes & fees
Apr 20 - Apr 21
Porta Pispini Residence

Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is CA $461
CA $523 total
includes taxes & fees
May 10 - May 11
Borgo Lucignanello Bandini

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is CA $344
CA $385 total
includes taxes & fees
Apr 27 - Apr 28
Castello di Gargonza

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is CA $312
CA $351 total
includes taxes & fees
Apr 19 - Apr 20
Albergo Diffuso Borgo Santo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montechiaro Hotel Reviews

Find out more about Montechiaro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montechiaro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Montechiaro?

Yes, we have vacation rentals close to well known attractions in Montechiaro, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Montechiaro has to offer?

Borgo Argiano: Visitors like this Montechiaro vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an espresso maker. You can relax into your vacation with a garden and a library.

What’s there to see and do in Montechiaro?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Terme Antica Querciolaia. In the larger area, you’ll find Porta Romana and Siena State Archives.

What’s a vacation rental in Montechiaro like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Montechiaro. Vacation rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.