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Monsigliolo Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Monsigliolo vacation rentals

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ₩188,545
₩210,377 total
includes taxes & fees
Nov 4 - Nov 5
B&B Piccolo Hotel
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

2. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is ₩451,097
₩502,161 total
includes taxes & fees
Nov 15 - Nov 16
Fontelunga Hotel & Villas
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ₩274,054
₩303,692 total
includes taxes & fees
Nov 5 - Nov 6
CASA AMBRA
Terrace/patio

4. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is ₩158,953
₩180,804 total
includes taxes & fees
Nov 5 - Nov 6
Casale dell'Assiolo
A couple relaxing in a spa setting with a visible logo on the wall, a reception desk, and a plant in the background.

5. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ₩177,420
₩201,117 total
includes taxes & fees
Nov 8 - Nov 9
San Michele al Borgo
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

6. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (49 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is ₩366,411
₩409,007 total
includes taxes & fees
Nov 3 - Nov 4
Castello di Gargonza
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

7. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is ₩107,995
₩124,750 total
includes taxes & fees
Nov 4 - Nov 5
Artisti del Cavallo Tourism
Pool

8. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (42 reviews)
"It was wonderful!"
United States
Wade
The price is ₩98,662
₩117,460 total
includes taxes & fees
Nov 18 - Nov 19
iConic Wellness Resort
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

9. 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 ₩86,477
₩99,591 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais
A spa area with a stone-walled arch, a hot tub, and a small window.

10. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ₩146,564
₩167,175 total
includes taxes & fees
Nov 9 - Nov 10
DormiVeglia B&B
A crowded restaurant with brick walls and multiple tables and chairs.

11. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 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 ₩200,298
₩226,283 total
includes taxes & fees
Nov 25 - Nov 26
La Locanda di San Francesco
A terrace with a table set for breakfast, overlooking a scenic landscape.

12. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ₩252,118
₩283,291 total
includes taxes & fees
Nov 11 - Nov 12
Delcorto Suites
Exterior

13. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is ₩159,554
₩181,467 total
includes taxes & fees
Nov 3 - Nov 4
montorio
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, (139 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is ₩306,932
₩343,580 total
includes taxes & fees
Nov 3 - Nov 4
Il Tosco
An interior courtyard with stone columns, arches, and a mosaic.

15. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (121 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 ₩212,133
₩239,301 total
includes taxes & fees
Nov 3 - Nov 4
Meublé Il Riccio
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

16. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ₩132,869
₩149,133 total
includes taxes & fees
Nov 3 - Nov 4
Vicolo Della Scala Rooms - La Luna
A rustic brick building with a mural, a clock, and various potted plants.

17. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is ₩110,840
₩144,254 total
includes taxes & fees
Nov 22 - Nov 23
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A patio area with outdoor seating, potted plants, and a view of the landscape.

18. 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 ₩144,331
₩195,833 total
includes taxes & fees
Nov 3 - Nov 4
Affitacamere Maria Gabriella
A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

19. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (5 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is ₩86,610
₩121,323 total
includes taxes & fees
Nov 3 - Nov 4
Limehome Arezzo Duomo
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

20. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (169 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is ₩182,247
₩209,404 total
includes taxes & fees
Nov 5 - Nov 6
Hotel San Gregorio
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 Monsigliolo Hotel Reviews

B&B Hotel Arezzo

B&B Hotel Arezzo

10/10 Excellent
"This is a suitable hotel for one or two nights. Staff very helpful."
JUAN 1-night trip
Posted 2 days ago
B&B Hotel Arezzo

Find out more about Monsigliolo

Search for Vacation rentals in Monsigliolo on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Monsigliolo using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Monsigliolo?

Yes, there are vacation rentals near popular sights in Monsigliolo, or you can choose a more secluded option if you'd like a relaxing place to stay.

How many vacation rentals are there in Monsigliolo?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Monsigliolo stay.

What’s there to see and do in Monsigliolo?

Explore the area and family-friendly sights such as Naturalistic Oasis La Valle, or get out into nature at a spot like Isola Maggiore. Piazza della Repubblica and Villa Bramasole are a couple of places you'll find in the larger area.

What’s a vacation rental in Monsigliolo like?

Vacation rentals are private properties you can book for several days or longer in Monsigliolo. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.