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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Montechiaro holiday rentals

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is 4.547.121 ₫
5.094.505 ₫ total
includes taxes & fees
4 May - 5 May
Villa Montecastello
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 1.833.869 ₫
2.418.835 ₫ total
includes taxes & fees
6 May - 7 May
Tuscasì Aparthotel
Exterior

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 2.811.902 ₫
3.216.656 ₫ total
includes taxes & fees
6 May - 7 May
Il Pozzo di Sant'Andrea
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is 2.934.623 ₫
3.351.648 ₫ total
includes taxes & fees
5 May - 6 May
Fullino Nero
Food court

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 3.412.025 ₫
5.946.472 ₫ total
includes taxes & fees
6 May - 7 May
Borgo Il Poggiaccio
Food court

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 4.675.626 ₫
5.235.984 ₫ total
includes taxes & fees
2 Jun - 3 Jun
Antico Borgo Poggiarello
Interior detail

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 3.493.745 ₫
3.966.683 ₫ total
includes taxes & fees
18 May - 19 May
La Coroncina Lodging
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (22 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 3.371.586 ₫
3.801.417 ₫ total
includes taxes & fees
7 May - 8 May
Casa di Campagna in Toscana
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 2.533.804 ₫
2.910.747 ₫ total
includes taxes & fees
4 May - 5 May
DormiVeglia B&B
Lunch and dinner served, local cuisine

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 6.669.597 ₫
7.460.120 ₫ total
includes taxes & fees
4 May - 5 May
Castello di Gargonza
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (171 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 3.155.492 ₫
3.718.322 ₫ total
includes taxes & fees
21 May - 22 May
Bosco della Spina
Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is 6.116.371 ₫
6.882.463 ₫ total
includes taxes & fees
4 May - 5 May
Albergo Diffuso Borgo Santo
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is 3.415.592 ₫
3.819.026 ₫ total
includes taxes & fees
14 May - 15 May
Palazzo Pacini
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
The price is 2.123.038 ₫
2.458.905 ₫ total
includes taxes & fees
12 May - 13 May
Villa Fontis Rapolano
Seasonal outdoor pool, pool umbrellas, pool loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (41 reviews)
"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
The price is 2.790.601 ₫
3.255.006 ₫ total
includes taxes & fees
6 May - 7 May
Villa San Filippo
Terrace/patio

Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is 9.688.467 ₫
10.966.221 ₫ total
includes taxes & fees
5 May - 6 May
Borgo Lucignanello Bandini
Front of property

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30 reviews)
"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
The price is 2.879.251 ₫
3.290.739 ₫ total
includes taxes & fees
6 May - 7 May
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

Borgo San Felice Resort

Borgo San Felice Resort

10/10 Excellent
"Just book it, the accommodations, staff, venue are absolutely amazing. Easy day trips to Siena, San Gimignano and a great little gem, Monteriggioni if you have the time and want a less touristy medieval feel. We will definitely be back."
Barbara 4-night trip
Posted 9 hours ago
Borgo San Felice Resort

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’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 wider area, you’ll find Porta Romana and Siena State Archives.

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.