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Monsigliolo Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Monsigliolo vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is P9,041
P10,233 total
includes taxes & fees
Aug 29 - Aug 30
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, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is P16,685
P18,642 total
includes taxes & fees
Aug 24 - Aug 25
Fontelunga Hotel & Villas
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

3. 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 P9,041
P10,234 total
includes taxes & fees
Aug 24 - Aug 25
San Michele al Borgo
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is P6,433
P7,364 total
includes taxes & fees
Aug 25 - Aug 26
Vicolo Della Scala Rooms - La Luna
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

5. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is P8,845
P9,945 total
includes taxes & fees
Sep 16 - Sep 17
CASA AMBRA
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
9.2 out of 10, Wonderful, (44 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is P15,560
P17,405 total
includes taxes & fees
Sep 1 - Sep 2
Castello di Gargonza

7. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is P7,430
P8,461 total
includes taxes & fees
Sep 7 - Sep 8
Casale dell'Assiolo
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

8. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P11,204
P12,540 total
includes taxes & fees
Aug 30 - Aug 31
Abbadia Sicille Relais
A terrace with a table set for breakfast, overlooking a scenic landscape.

9. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (41 reviews)
"A beautiful historic property in the centre of Montepulciano. Very spacious room looking out on the Main Street. Wonderful gourmet breakfast provided each morning! I will recommend this property!"
Canada
James
The price is P10,985
P12,372 total
includes taxes & fees
Aug 24 - Aug 25
Delcorto Suites
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, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is P8,029
P9,120 total
includes taxes & fees
Aug 24 - Aug 25
DormiVeglia B&B
An arched doorway leading to a building with a wooden door and a staircase.

11. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 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 P4,899
P5,677 total
includes taxes & fees
Aug 30 - Aug 31
Residenza Fabroni
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

Hotel Corsignano

Hotel Corsignano

8/10 Good
"A cute little hotel, room was a bit smaller. Breakfast was amazing and you cant beat the location."
Minna 2-night trip
Posted 1 day ago
Hotel Corsignano

Find out more about Monsigliolo

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

  • View our selection of featured holiday rentals in Monsigliolo
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Look no further and take a look at our great range of rental properties in Monsigliolo!

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 Cortona Cathedral 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.