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Our top choices for Monsigliolo hotels

La Bandita Townhouse

La Bandita Townhouse
Pienza
10.0 out of 10, Exceptional, (6)
"Fabulous hotel - comfortable, quiet and the staff is incredibly friendly. Looking forward to my next stay! "
United States
Elin
The price is AU$710
includes taxes & fees
19 Dec - 20 Dec
La Bandita Townhouse

I Capricci di Merion Resort & Spa

I Capricci di Merion Resort & Spa
Tuoro sul Trasimeno
9.8 out of 10, Exceptional, (46)
"This property is so beautiful and the food at the resturant was fantastic. Our only complaint was the spa, the sauna was great, but the hottub was lukewarm and there was so much chlorine it made our eyes burn and we had to get out almost immediately. Otherwise a perfect experience!"
United States
Bliss
I Capricci di Merion Resort & Spa

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
5.0 star property
Cortona Old Town
10.0 out of 10, Exceptional, (254)
"Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return. "
Canada
Florence and Robert
The price is AU$509
includes taxes & fees
4 Jan - 5 Jan 2026
Monastero di Cortona Hotel & Spa

Agriturismo Merigge Wellness & Spa

Agriturismo Merigge Wellness & Spa
Montepulciano
9.8 out of 10, Exceptional, (81)
"Friendly staff and super accommodating. We would highly recommend staying there!!!"
United States
Scott
The price is AU$408
includes taxes & fees
22 Dec - 23 Dec
Agriturismo Merigge Wellness & Spa

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (13)
"Excellent room and food. Great location!"
United States
Saurabh
The price is AU$455
includes taxes & fees
29 Dec - 30 Dec
Poggio Paradiso Resort & Spa

Nobilis Charme Relais

Nobilis Charme Relais
Montepulciano
8.8 out of 10, Excellent, (6)
"Was a spectacular room and bathroom, pool area was comfortable and pleasant place to spend time. Nice breakfast and good service. Large patio area with lovely views. Is about a 25 minute walk up hill to montepulciano which is a lovely place to spend the evening - worth booking the restaurants in town. The path from the hotel through the broken gate could really do with a bit of tlc"
United Kingdom
alison
The price is AU$279
includes taxes & fees
19 Dec - 20 Dec
Nobilis Charme Relais

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is AU$351
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (279)
"Great room and service"
United States
ALFREDO
The price is AU$252
includes taxes & fees
21 Dec - 22 Dec
Relais Villa Grazianella - UNA Esperienze

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
The price is AU$187
includes taxes & fees
19 Dec - 20 Dec
Bed & Breakfast Vicolo dell'Oste

Terra Antica Resort

Terra Antica Resort
Montepulciano
10.0 out of 10, Exceptional, (20)
"Great stay in Montepulciano "
United States
Jonathan
The price is AU$620
includes taxes & fees
23 Dec - 24 Dec
Terra Antica Resort

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.4 out of 10, Exceptional, (52)
"Such a quiet and beautiful property, the hosts provided everything that was needed, and the location was great for visiting local Cantinas and Vineyards "
United States
Justin
The price is AU$154
includes taxes & fees
19 Dec - 20 Dec
Locanda Vesuna

Bed & Breakfast Viziottavo

Bed & Breakfast Viziottavo
Castiglion Fiorentino
10.0 out of 10, Exceptional, (9)
"Struttura molto pulita e tranquilla particolare per l' ispirazione Dantesca delle camere, personale gentilissimo e disponibile. Ci ritorneremo volentieri "
Italy
luigi
The price is AU$194
includes taxes & fees
28 Dec - 29 Dec
Bed & Breakfast Viziottavo

LaChiusa Tuscany

LaChiusa Tuscany
3.0 star property
Torrita di Siena
9.2 out of 10, Wonderful, (66)
"This is such a cute fun traditional Tuscan place to stay! Everywhere you look is an amazing view. The dinner was fantastic. The breakfast was delicious. The bed was super comfortable. The room, while rustic and vintage, was very nice. It was so peaceful and quiet! We thoroughly enjoyed our stay and the drive through Tuscany to get there. Bonus that it’s near Maximus’s house from the gladiator movie sights!"
United States
Brent
The price is AU$399
includes taxes & fees
19 Dec - 20 Dec
LaChiusa Tuscany

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is AU$260
includes taxes & fees
30 Dec - 31 Dec
Meublé Il Riccio

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is AU$403
includes taxes & fees
22 Dec - 23 Dec
Il Tosco

Podere La Rocca

Podere La Rocca
Montepulciano
9.8 out of 10, Exceptional, (93)
"Clean room, great food and amazingly helpful staff!"
United States
Ronald
Podere La Rocca

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (130)
"Great room-great staff-great location"
United States
Richard
The price is AU$284
includes taxes & fees
18 Jan - 19 Jan 2026
La Locanda di San Francesco

Palazzo Mosela Alla Porta

Palazzo Mosela Alla Porta
Montepulciano
9.0 out of 10, Wonderful, (170)
"Great spot for a quick stay and convenient to main railway station"
Australia
Julianne
The price is AU$224
includes taxes & fees
19 Dec - 20 Dec
Palazzo Mosela Alla Porta

Palazzo Pio III

Palazzo Pio III
Sarteano
10.0 out of 10, Exceptional, (3)
"Great stay at this hotel. Amazing breakfast and very warm welcome. I highly recommend Palazzo Pio III! Everything was perfect!"
Canada
Geneviève
Palazzo Pio III

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
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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Frequently asked questions

Where is the best place for a stay in Monsigliolo?
Located 3 mi (4.9 km) from the heart of Monsigliolo, Monastero di Cortona Hotel & Spa is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are Relais Villa Grazianella - UNA Esperienze and Grand Hotel Admiral Palace. See all available top hotels, or vacation rentals in Monsigliolo.
What are some of the best holiday rentals that Monsigliolo has to offer?
Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Monsigliolo is located in a rural location, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Make the most of garden in this rental home to help you unwind. See all vacation rentals in Monsigliolo.
If I need to cancel my hotel reservation in Monsigliolo, will I receive a refund?
Yes! Most hotel reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Monsigliolo.
What are some hotels with pools in Monsigliolo?
Monastero di Cortona Hotel & Spa: Features a full-service spa, an indoor pool and a sauna. Relais Villa Grazianella - UNA Esperienze and Grand Hotel Admiral Palace are a couple of other choices that offer an on-site pool. View all hotels with pools in Monsigliolo.
What is staying in Monsigliolo like?
Travellers to Monsigliolo will find plenty to explore and enjoy. In Monsigliolo, there are 11 hotels and other accommodation options to choose from. Find out more about Monsigliolo.
What are the top places to visit in Monsigliolo?
Places to visit in the wider area include Piazza della Repubblica, Giuseppe Garibaldi Memorial and Villa Bramasole. You'll also find La Braccesca Winery and Tennis Club Castiglionese in the area. Take a look at what more there is to see and do in Expedia's Monsigliolo guide.
What's the seasonal weather like in Monsigliolo?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Monsigliolo is 906 mm.

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