A stone building with red shutters, a tree in the foreground, and a staircase leading to an upper level.

Monticchiello Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Monticchiello holiday rentals

A patio area with outdoor seating, potted plants, and a view of the landscape.

1. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (70 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is S$174
includes taxes & fees
13 Oct - 14 Oct
Affitacamere Maria Gabriella
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

2. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (161 reviews)
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
United States
Julia
The price is S$191
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
An interior courtyard with stone columns, arches, and a mosaic.

3. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is S$210
includes taxes & fees
17 Oct - 18 Oct
Meublé Il Riccio
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

4. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (134 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is S$331
includes taxes & fees
2 Nov - 3 Nov
Il Tosco
A crowded restaurant with brick walls and multiple tables and chairs.

5. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (150 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is S$261
includes taxes & fees
3 Nov - 4 Nov
La Locanda di San Francesco
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

6. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is S$154
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
Front of property

7. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is S$165
includes taxes & fees
18 Oct - 19 Oct
montorio
A terrace with a table set for breakfast, overlooking a scenic landscape.

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (46 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is S$257
includes taxes & fees
10 Nov - 11 Nov
Delcorto Suites
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

9. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is S$637
includes taxes & fees
2 Nov - 3 Nov
L'Olmo
An arched doorway leading to a building with a wooden door and a staircase.

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (113 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is S$110
includes taxes & fees
13 Oct - 14 Oct
Residenza Fabroni
A poolside area with two glasses of water, candles, and a stone pathway.

11. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is S$246
includes taxes & fees
12 Oct - 13 Oct
Casanova - Panoramic Rooms and Suites
A historic building with a tower, a courtyard, and a well-lit entrance.

12. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is S$115
includes taxes & fees
10 Nov - 11 Nov
Abbadia Sicille Relais
A wooden door with a sign, a staircase with blue steps, and a metal handrail.

13. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is S$126
includes taxes & fees
6 Nov - 7 Nov
PienzaLettings Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

14. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is S$112
includes taxes & fees
5 Nov - 6 Nov
TuscanyLettings Studio&Room
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

15. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
The price is S$176
includes taxes & fees
2 Nov - 3 Nov
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

16. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is S$170
includes taxes & fees
14 Oct - 15 Oct
B&B Le Scalette di Piazza
A stone building with a wooden door, a staircase, and a small window with a metal grill.

17. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is S$138
includes taxes & fees
1 Nov - 2 Nov
Casa Gioia - Casa Olivieri
A stone building with a courtyard, outdoor seating, and a warm light setting.

18. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is S$163
includes taxes & fees
2 Nov - 3 Nov
Sarna Residence
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

19. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (10 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is S$352
includes taxes & fees
10 Nov - 11 Nov
Palazzo Saloni
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

20. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is S$153
includes taxes & fees
22 Oct - 23 Oct
Idolina Guest House
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 Monticchiello Hotel Reviews

Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

8/10 Good
"Ok."
Yuanjun 1-night trip
Posted 14 hours ago
Hotel Panoramic Montepulciano

Frequently asked questions

Are there holiday rentals in Monticchiello?

Yes, there are holiday rentals in Monticchiello close to Art Studio di Adelina Quadri, or you can select a more secluded option if you're looking for a relaxing stay. Monticchiello is known for its art.

How many holiday rentals will I find in Monticchiello?

Expedia has 8 holiday rentals for your stay in Monticchiello.

What can I see and do in Monticchiello?

Explore the area and family-friendly sights such as Pinzi Pinzuti, or get out into nature at a spot like Historic Centre of Pienza. Art Studio di Adelina Quadri and Pienza Cathedral are a couple of places you'll find in the wider area.

What are holiday rentals like in Monticchiello?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monticchiello. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.