Default HTG hotel image

Monsigliolo 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Monsigliolo holiday 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, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is RM588
RM666 total
includes taxes & fees
7 Oct - 8 Oct
B&B Piccolo Hotel
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

2. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is RM414
RM474 total
includes taxes & fees
30 Sept - 1 Oct
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.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is RM1,329
RM1,476 total
includes taxes & fees
1 Oct - 2 Oct
CASA AMBRA
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

4. 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 RM582
RM659 total
includes taxes & fees
29 Sept - 30 Sept
San Michele al Borgo
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

5. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
The price is RM1,215
RM1,356 total
includes taxes & fees
11 Oct - 12 Oct
Fontelunga Hotel & Villas
Terrace/patio

6. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is RM543
RM616 total
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo
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 RM337
RM389 total
includes taxes & fees
29 Sept - 30 Sept
Artisti del Cavallo Tourism
An interior courtyard with stone columns, arches, and a mosaic.

8. 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 RM661
RM746 total
includes taxes & fees
1 Oct - 2 Oct
Meublé Il Riccio
A historic building with a tower, a courtyard, and a well-lit entrance.

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is RM505
RM569 total
includes taxes & fees
25 Oct - 26 Oct
Abbadia Sicille Relais
A fountain with water cascading down a column, surrounded by greenery and a building in the background.

10. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is RM381
RM437 total
includes taxes & fees
29 Sept - 30 Sept
Residence al Lago
A patio area with outdoor seating, potted plants, and a view of the landscape.

11. 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
The price is RM450
RM610 total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
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 Monsigliolo Hotel Reviews

Villa Tiberini Wine Relais

Villa Tiberini Wine Relais

10/10 Excellent
"It's great place for the large family."
ENLI 3-night trip
Posted 6 hours ago
Villa Tiberini Wine Relais

Find out more about Monsigliolo

Search for holiday rentals in Monsigliolo on Expedia.co.uk! 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
  • Use the map to find apartments and other holiday homes in the Monsigliolo neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Monsigliolo while they last

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

Frequently asked questions

Can I find a holiday rental in Monsigliolo?

Yes, there are holiday rentals close to the most popular sights in Monsigliolo, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Monsigliolo?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Monsigliolo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monsigliolo. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.