Default HTG hotel image

Montechiaro Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montechiaro vacation rentals

A villa with a swimming pool, outdoor seating, and a tennis court.

1. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is AED 569
AED 643 total
includes taxes & fees
4 Oct - 5 Oct
Villa Curina Resort
A stone building with a garden in front.

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is AED 877
AED 998 total
includes taxes & fees
1 Oct - 2 Oct
Borgo Argenina
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

3. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
Ca' Bianca Tuscany Relais
A table with two wine glasses, a bottle, and a book.

4. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is AED 247
AED 288 total
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
A bakery display with pastries and a coffee station.

5. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (211 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is AED 422
AED 480 total
includes taxes & fees
30 Oct - 31 Oct
B&B Il Corso
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

6. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is AED 573
AED 798 total
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto
A bathroom with a window view of a historic building and a tiled roof.

7. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is AED 397
AED 453 total
includes taxes & fees
27 Oct - 28 Oct
Siena Vip
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

8. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AED 247
AED 326 total
includes taxes & fees
31 Oct - 1 Nov
Tuscasì Aparthotel
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

9. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (51 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is AED 528
AED 598 total
includes taxes & fees
25 Oct - 26 Oct
Guild Living Siena Senior Resort & Residence
A bedroom with a large bed, bedside tables, a window, a radiator, and a TV.

10. Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (3 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is AED 666
AED 783 total
includes taxes & fees
8 Oct - 9 Oct
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
A bedroom with a bed, bedside table, and a window with a view of greenery.

11. 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 AED 491
AED 557 total
includes taxes & fees
21 Oct - 22 Oct
La Coroncina Lodging
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

12. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is AED 334
AED 443 total
includes taxes & fees
27 Oct - 28 Oct
Peaceful corner with garden between Chianti and Crete, very close to Old Town
A traditional stone building with a courtyard, a staircase, and potted plants.

13. 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 AED 372
AED 425 total
includes taxes & fees
19 Oct - 20 Oct
Il Pozzo di Sant'Andrea
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

14. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (347 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is AED 312
AED 359 total
includes taxes & fees
12 Oct - 13 Oct
ApartHotel Anghel
A room with a bed, a leather sofa, and a window with a view of a building outside.

15. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (104 reviews)
"Great location."
Canada
Marie-Christine
The price is AED 259
AED 338 total
includes taxes & fees
8 Oct - 9 Oct
Al Mercato B&B
A rustic stone building with a courtyard.

16. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is AED 397
AED 453 total
includes taxes & fees
5 Oct - 6 Oct
Fullino Nero
A building with a sign reading 'Villa Le Camelie' and multiple flags.

17. Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is AED 304
AED 351 total
includes taxes & fees
29 Oct - 30 Oct
Villa le Camelie Siena
A table set with breakfast items on a balcony overlooking a historic town.

18. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (131 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
The price is AED 698
AED 784 total
includes taxes & fees
30 Oct - 31 Oct
Residenza d'Epoca Palazzo Borghesi
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

19. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is AED 487
AED 552 total
includes taxes & fees
29 Oct - 30 Oct
La Terrazza Sul Campo Rooming House
A modern building with a sign reading "PORTA PISPINI" and a staircase leading to an entrance.

20. Porta Pispini Residence

Porta Pispini Residence
2.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (24 reviews)
"A fabulous property - well appointed and equipped. Very modern, clean and quiet. We enjoyed our daily walks into Siena via the Porta Pispini. We would love to stay here again."
Canada
Michael
Porta Pispini Residence
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montechiaro Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"good to stay"
Jinhee 1-night trip
Posted 9 hours ago
La Certosa di Pontignano

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 kitchenware. 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.