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

Monticchiello 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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Monticchiello vacation 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, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ￥15,003
￥20,881 total
includes taxes & fees
Oct 28 - Oct 29
Affitacamere Maria Gabriella
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

2. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ￥17,584
￥21,452 total
includes taxes & fees
Nov 2 - Nov 3
"Il Focolare" Superior Apartment in Monticchiello
A bedroom with a bed, a desk, and a chair. There is a wooden ceiling and a window.

3. The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (13 reviews)
"Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay."
United States
Melissa B.
The price is ￥15,826
￥19,733 total
includes taxes & fees
Oct 25 - Oct 26
The house in the village - Angelica apartment - Vald'Orcia
An arched doorway leading to a building with a wooden door and a staircase.

4. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (115 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
The price is ￥14,179
￥16,300 total
includes taxes & fees
Nov 3 - Nov 4
Residenza Fabroni
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

5. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (166 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is ￥22,659
￥25,981 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
A historic building with a tower, a courtyard, and a well-lit entrance.

6. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is ￥10,955
￥12,579 total
includes taxes & fees
Nov 23 - Nov 24
Abbadia Sicille Relais
An interior courtyard with stone columns, arches, and a mosaic.

7. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 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 ￥24,557
￥27,716 total
includes taxes & fees
Oct 28 - Oct 29
Meublé Il Riccio
Exterior

8. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is ￥17,697
￥20,169 total
includes taxes & fees
Oct 30 - Oct 31
montorio
A crowded restaurant with brick walls and multiple tables and chairs.

9. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (151 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 ￥25,418
￥28,663 total
includes taxes & fees
Nov 15 - Nov 16
La Locanda di San Francesco
A terrace with a table set for breakfast, overlooking a scenic landscape.

10. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (48 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ￥29,649
￥33,317 total
includes taxes & fees
Nov 23 - Nov 24
Delcorto Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

11. 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 ￥12,974
￥14,982 total
includes taxes & fees
Nov 5 - Nov 6
TuscanyLettings Studio&Room
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

12. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (6 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ￥12,812
￥14,803 total
includes taxes & fees
Nov 2 - Nov 3
PienzaLettings Suites
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

13. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 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 ￥16,051
￥18,359 total
includes taxes & fees
Nov 22 - Nov 23
Bed & Breakfast Vicolo dell'Oste
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

14. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (138 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is ￥36,256
￥40,585 total
includes taxes & fees
Nov 2 - Nov 3
Il Tosco
A stone building with a wooden door, a staircase, and a small window with a metal grill.

15. 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 ￥17,804
￥20,295 total
includes taxes & fees
Oct 28 - Oct 29
Casa Gioia - Casa Olivieri
A stone archway leading to a building entrance with a wooden door.

16. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
5.6 out of 10, (5 reviews)
"Na"
United States
Abel
The price is ￥8,306
￥9,845 total
includes taxes & fees
Nov 5 - Nov 6
Bellarmino Boutique Apartments
A cozy living room with a fireplace, a sofa, and a TV.

17. 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 ￥70,338
￥78,075 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

18. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is ￥14,373
￥17,218 total
includes taxes & fees
Nov 14 - Nov 15
Idolina Guest House
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

19. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (12 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is ￥44,033
￥50,194 total
includes taxes & fees
Nov 2 - Nov 3
Palazzo Saloni
A poolside area with two glasses of water, candles, and a stone pathway.

20. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (103 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is ￥26,728
￥30,104 total
includes taxes & fees
Oct 27 - Oct 28
Casanova - Panoramic Rooms and Suites
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 Monticchiello Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."
Charles 6-night trip
Posted 6 hours ago
Castello di Velona Resort Thermal SPA & Winery

Find out more about Monticchiello

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

  • View our selection of featured holiday rentals in Monticchiello
  • Use the map to find apartments and other holiday homes in the Monticchiello neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Monticchiello while they last

Look no further and take a look at our great range of rental properties in Monticchiello!

Frequently asked questions

Are there vacation rentals in Monticchiello?

Yes, we give you a choice of vacation rentals in Monticchiello close to Art Studio di Adelina Quadri, or you can go with a more remote option if you're looking for a relaxing stay. Monticchiello is known for its art.

What's the top vacation rental in Monticchiello?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental outside of Monticchiello is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Monticchiello?

Expedia has 8 vacation 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 larger area.

What are vacation rentals like in Monticchiello?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Monticchiello. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.