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

Monticchiello Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$120 nightly
The price is $136
Oct 7 - Oct 8
Total with taxes and fees
Affitacamere Maria Gabriella
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

2. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
$717 nightly
The price is $793
Oct 18 - Oct 19
Total with taxes and fees
L'Olmo
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

3. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (157 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
$197 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
Hotel San Gregorio
An interior courtyard with stone columns, arches, and a mosaic.

4. 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
$149 nightly
The price is $169
Oct 25 - Oct 26
Total with taxes and fees
Meublé Il Riccio
An arched doorway leading to a building with a wooden door and a staircase.

5. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (110 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
$90 nightly
The price is $104
Oct 26 - Oct 27
Total with taxes and fees
Residenza Fabroni
A crowded restaurant with brick walls and multiple tables and chairs.

6. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (148 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
$212 nightly
The price is $238
Sep 27 - Sep 28
Total with taxes and fees
La Locanda di San Francesco
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

7. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (131 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
$357 nightly
The price is $397
Oct 3 - Oct 4
Total with taxes and fees
Il Tosco
A terrace with a table set for breakfast, overlooking a scenic landscape.

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (44 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
$190 nightly
The price is $213
Oct 6 - Oct 7
Total with taxes and fees
Delcorto Suites
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

9. 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
$123 nightly
The price is $140
Oct 14 - Oct 15
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

10. 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
$99 nightly
The price is $114
Oct 26 - Oct 27
Total with taxes and fees
TuscanyLettings Studio&Room
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, (97 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
$173 nightly
The price is $195
Oct 4 - Oct 5
Total with taxes and fees
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, (182 reviews)
"Great Historical location."
Canada
Robert
$124 nightly
The price is $140
Oct 25 - Oct 26
Total with taxes and fees
Abbadia Sicille Relais
A stone building with a wooden door, a staircase, and a small window with a metal grill.

13. 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
$100 nightly
The price is $115
Oct 19 - Oct 20
Total with taxes and fees
Casa Gioia - Casa Olivieri
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

14. 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
$94 nightly
The price is $108
Oct 25 - Oct 26
Total with taxes and fees
PienzaLettings Suites
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

15. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
$267 nightly
The price is $272
Oct 5 - Oct 6
Total with taxes and fees
Suite Gioconda - Podere Casa Rossa in Pienza

16. Mery's House- elegant apartment

Mery's House- elegant apartment
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"Our accommodations were awesome for 4 adults. Mery was a gracious host and made sure everything was to our likening. There was ample parking and close to old town."
Canada
Anna
$404 nightly
The price is $408
Sep 30 - Oct 1
Total with taxes and fees
Mery's House- elegant apartment

17. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
$115 nightly
The price is $131
Oct 5 - Oct 6
Total with taxes and fees
montorio
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

18. 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, (49 reviews)
"Our stay was great. "
United States
Elena
$173 nightly
The price is $195
Oct 26 - Oct 27
Total with taxes and fees
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

19. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
$316 nightly
The price is $321
Sep 27 - Sep 28
Total with taxes and fees
Oasi del Borgo Montefollonico
A table with a coffee pot, cups, and newspapers on a balcony overlooking a hilly landscape.

20. Apartment 'Entro le mura' with Balcony & Wi-Fi

Apartment 'Entro le mura' with Balcony & Wi-Fi
Montepulciano
9.8 out of 10, Exceptional, (12 reviews)
"Everything was clean and neat. A lovely view. We received help with parking and luggage from Enrico, who also treated us to a bottle of wine. "
Canada
Heather M.
$344 nightly
The price is $348
Sep 26 - Sep 27
Total with taxes and fees
Apartment 'Entro le mura' with Balcony & Wi-Fi
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

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

10/10 Excellent
"The room snd entire property were spotless clean. Staff wete helpful and friendly. Our room and patio overlooked the d'Orcia valley, gorgeous any time, especially in the morning. The entire grounds, pool, loungers, plants were well maintained. This was our third time at Cassanova and we would come again. A short walk into San Quirico d'Orcia with several good restaurants and a COOP store for drinks and groceries."
Zoltan 5-night trip
Posted 3 hours ago
Casanova - Panoramic Rooms and Suites

Find out more about Monticchiello

Everything you need to know about Monticchiello vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monticchiello vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monticchiello vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monticchiello vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monticchiello. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Monticchiello in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monticchiello rentals

At Expedia, we put the best Monticchiello vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Monticchiello rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monticchiello vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monticchiello. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.