Default HTG hotel image

Monsigliolo Holiday 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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Monsigliolo holiday rentals

Lobby

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 HK$1,146
HK$1,296 total
includes taxes & fees
16 Aug - 17 Aug
B&B Piccolo Hotel
Exterior

2. 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 HK$1,135
HK$1,284 total
includes taxes & fees
23 Aug - 24 Aug
San Michele al Borgo
Front of property

3. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is HK$807
HK$924 total
includes taxes & fees
17 Aug - 18 Aug
Vicolo Della Scala Rooms - La Luna
Courtyard

4. 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 HK$1,908
HK$2,135 total
includes taxes & fees
17 Aug - 18 Aug
Fontelunga Hotel & Villas
Lunch and dinner served

5. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (43 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is HK$1,953
HK$2,184 total
includes taxes & fees
15 Aug - 16 Aug
Castello di Gargonza
Terrace/patio

6. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is HK$933
HK$1,062 total
includes taxes & fees
7 Sept - 8 Sept
Casale dell'Assiolo
Terrace/patio

7. 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 HK$1,488
HK$1,663 total
includes taxes & fees
23 Aug - 24 Aug
Abbadia Sicille Relais
Terrace/patio

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is HK$1,540
HK$1,731 total
includes taxes & fees
16 Aug - 17 Aug
Delcorto Suites
Private spa tub

9. 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 HK$1,008
HK$1,145 total
includes taxes & fees
16 Aug - 17 Aug
DormiVeglia B&B
Property entrance

10. 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 HK$715
HK$823 total
includes taxes & fees
21 Aug - 22 Aug
Residenza Fabroni
Exterior

11. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is HK$656
HK$758 total
includes taxes & fees
16 Aug - 17 Aug
Artisti del Cavallo Tourism
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

12. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (39 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is HK$1,014
HK$1,170 total
includes taxes & fees
10 Sept - 11 Sept
iConic Wellness Resort
Front of property

13. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is HK$902
HK$1,029 total
includes taxes & fees
25 Aug - 26 Aug
Vicolo Della Scala Rooms - Il Sole
Exterior

14. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is HK$1,533
HK$1,704 total
includes taxes & fees
1 Sept - 2 Sept
Borgo Dolciano
Bar (on property)

15. La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is HK$961
HK$1,075 total
includes taxes & fees
16 Aug - 17 Aug
La Piccola Locanda
Property entrance

16. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (130 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
The price is HK$2,321
HK$2,589 total
includes taxes & fees
16 Aug - 17 Aug
Il Tosco
Courtyard view

17. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is HK$5,699
HK$6,305 total
includes taxes & fees
16 Aug - 17 Aug
L'Olmo
Interior

18. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is HK$1,289
HK$1,454 total
includes taxes & fees
15 Aug - 16 Aug
Meublé Il Riccio
Food court

19. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (147 reviews)
"Incredible views from our room"
United Kingdom
Isabelle
The price is HK$1,069
HK$1,212 total
includes taxes & fees
25 Aug - 26 Aug
La Locanda di San Francesco
Exterior

20. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 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 HK$1,064
HK$1,206 total
includes taxes & fees
20 Aug - 21 Aug
Bed & Breakfast Vicolo dell'Oste
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

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Magnifique hôtel, service exceptionnel, propreté impeccable et excellente nourriture. Nous y retournerons sans aucun doute."
Isabelle 3-night trip
Posted 23 hours ago
Relais Villa Grazianella - UNA Esperienze

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
  • 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.

What are some of the best holiday rentals that Monsigliolo has to offer?

La Dolce Collina: This holiday home rental outside Monsigliolo is located in a rural location, and has a garden, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and kitchenware.

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.