Name: Hotel Relais II Chiostro di Pienza
Price range: CA $130
Rating: 8.8

Your Monsigliolo Vacation

Book a Monsigliolo vacation package and get ready to experience the best of this lively city. Consider staying in the neighborhood of Contrada Castello, which is great for dining, views and culture. Fill your itinerary with tours of Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona, some of the top attractions you just have to see during your trip to Monsigliolo. Don't delay your visit to this city any longer. The ultimate Monsigliolo vacation is a couple of clicks away with Expedia.

Top Monsigliolo Vacation Deals

Price found within the past 48 hours. Click for updated prices.

The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $1,844

per person

Jun 5 - Jun 11

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.6/10 Exceptional! (512 reviews)

Very nice - modern and clean hotel with great breakfast and very helpful staff. just outside the hotel there is a tram line and mini bus stand to commute the different parts of town. The only negative part was smaller room size but all other positive features of the hotel and staff overcomes this minor deficiency.

Reviewed on Mar 30, 2026

Hotel Duomo Firenze

Historic Centre of Florence

CA $2,339

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.2/10 Wonderful! (1,002 reviews)

Charming room directly across from the Duomo. Friendly, accommodating staff and the chef at the breakfast buffet is amazing! He made a cotton candy cappuccino! City center location close to restaurants, attractions and shopping. Also lively at night.

Reviewed on Mar 31, 2026

Eurostars Florence Boutique

Historic Centre of Florence

CA $2,048

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.6/10 Excellent! (483 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Villa Cora

Oltrarno

CA $6,323

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.8/10 Exceptional! (472 reviews)

Amazing service and staff. Wow!

Reviewed on Feb 21, 2026

Bernini Palace

Historic Centre of Florence

CA $3,121

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.8/10 Exceptional! (1,010 reviews)

The location and staff were great. Highly recommend.

Reviewed on Mar 29, 2026

Ready to book your vacation to Monsigliolo?

Choose your dates

Monsigliolo Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $827

CA $922 total

Apr 23 - Apr 24

includes taxes & fees

9.8/10 Exceptional! (228 reviews)

Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI

Fully refundableReserve now, pay when you stay

CA $388

CA $433 total

Apr 12 - Apr 13

includes taxes & fees

9.8/10 Exceptional! (284 reviews)

Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone

Reviewed on Mar 21, 2026

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26 Pienza SI

Fully refundableReserve now, pay when you stay

CA $130

CA $153 total

Apr 9 - Apr 10

includes taxes & fees

8.8/10 Excellent! (635 reviews)

A little tired, extremely clean, with an amazing staff

Reviewed on Jan 1, 2026

See all 5,146 properties in Monsigliolo

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.