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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Montechiaro holiday rentals

Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ฿2,103
฿2,461 total
includes taxes & fees
22 Dec - 23 Dec
ApartHotel Anghel
Premium bedding, down duvets, pillow-top beds, minibar
Tuscasì Aparthotel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ฿2,086
฿2,777 total
includes taxes & fees
20 Dec - 21 Dec
Tuscasì Aparthotel
Tasting room
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
City view
Regis Condo

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Daily continental breakfast (EUR 20 per person)
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is ฿6,061
฿6,815 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

Camping Siena Colleverde
3.0 star property
Scacciapensieri
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Deluxe Apartment | Premium bedding, down duvets, in-room safe, desk
Borgo Argiano

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano
Interior detail
La Coroncina Lodging

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ฿2,860
฿3,294 total
includes taxes & fees
16 Dec - 17 Dec
La Coroncina Lodging
Front of property
Casa Ciseri

Casa Ciseri

Casa Ciseri
Siena City Centre
9.8 out of 10, Exceptional, (9)
"Very nice stay!"
United States
Danielle
The price is ฿8,316
฿9,296 total
includes taxes & fees
15 Dec - 16 Dec
Casa Ciseri
Terrace/patio
Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo
Barberino Tavarnelle
9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveller
Castello Del Nero - Podere San Filippo
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Exterior
Borgo Argenina

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22)
"A planned Tuscany trip in the making for over a year. Saw this property came up while doing research and had a wonderful and romantic history. The property was even more beautiful than the pictures posted. It definitely caters to all types of travellers. A perfect bed and breakfast stay. Definitely recommend and will be back again. "
Canada
Nancy
Borgo Argenina
24-inch flat-screen TV with digital channels, TV
Palazzo Lenzi

Palazzo Lenzi

Palazzo Lenzi
Siena City Centre
9.0 out of 10, Wonderful, (2)
"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "
United States
Daniel
The price is ฿7,323
฿8,204 total
includes taxes & fees
15 Dec - 16 Dec
Palazzo Lenzi
Aerial view
Bosco della Spina

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (169)
"Views are amazing. Staff are very pleasant and helpful. "
Canada
Maureen
Bosco della Spina
Aerial view
Riserva di Fizzano Residence

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (24)
"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
Riserva di Fizzano Residence
Seasonal outdoor pool, pool umbrellas, pool loungers
Villa San Filippo

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (40)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
Villa San Filippo
Panoramic Apartment (2) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.0 out of 10, Very good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ฿3,818
฿4,422 total
includes taxes & fees
15 Dec - 16 Dec
Casa Vacanze Squarcialupi
Exterior
The Balcony Suite -Piazza del Campo View

The Balcony Suite -Piazza del Campo View

The Balcony Suite -Piazza del Campo View
Siena City Centre
9.2 out of 10, Wonderful, (16)
"Perfect location to explore Siena, right on the Campo. The apartment was warm and comfortable. As to be expected in such a central location, the noise & music from then restaurants on the piazza was loud till the early hours on Saturday night (so bring earplugs) but the other night was fine. "
Australia
Nicola
The price is ฿3,895
฿4,543 total
includes taxes & fees
15 Dec - 16 Dec
The Balcony Suite -Piazza del Campo View
Front of property
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Front of property
Podere La Chiusella

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
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

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"The best in Siena."
David 1-night trip
Posted 1 day ago
Hotel Certosa Di Maggiano

Find out more about Montechiaro

Search for holiday rentals in Montechiaro on Expedia! You can easily find your home rentals, villas, holiday apartments in Montechiaro using one of the methods below:

  • View our selection of featured holiday rentals in Montechiaro
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Look no further and take a look at our great range of rental properties in Montechiaro!

Frequently asked questions

Can I find a holiday rental in Montechiaro?

Yes, there are holiday rentals close to the most popular sights in Montechiaro, or you can select a more secluded option if you're looking for a relaxing stay.

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

Agriturismo La Ferrozzola: This holiday home rental outside of Montechiaro offers a terrace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and kitchenware. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Chianti Sculpture Park. In the wider area, you’ll find Porta Romana and San Martino.

What’s a holiday rental in Montechiaro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montechiaro. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a small group gathering.