Name: Hotel Relais II Chiostro di Pienza
Rating: 8.8

Your Santa Maria Vacation

Come and experience this captivating city for yourself with a Santa Maria vacation package. Think about staying in the neighborhood of Marciano della Chiana, which is good for views and nature, and your time here is sure to be unforgettable. Church of S. Francesco is just one of the famous attractions to add to your itinerary during a trip to Santa Maria. Check out Expedia's extensive range of travel options and start planning your perfect vacation to Santa Maria now.

Top Santa Maria Vacation Deals

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

Aurum Firenze

Historic Centre of Florence

CA $1,571

per person

May 24 - May 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

7.6/10 Good! (1,006 reviews)

Breakfast was ok but we found it difficult to get healthy food. There seemed to be a finite amount of fruit and yogurt (managed to get a yogurt one morning out of four). That said we opted for 8 am breakfast and might have had more luck earlier. Hotel was well located and felt really secure. I would stay there again.

Reviewed on Apr 13, 2026

Precise Tale Poggio Alla Sala

CA $2,657

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.4/10 Exceptional! (124 reviews)

Absolutely an amazing stay. Very charming and well kept. Essentially a resort with a palatial feel. Loved walking the grounds and relaxing. Excellent restaurant, breakfast was included. The setting is quiet and beautiful. Will book again.

Reviewed on Apr 13, 2026

EXE Toscana

Lucca Historical Center

CA $2,492

per person

May 19 - May 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

8.4/10 Very Good! (825 reviews)

Room was run down and the breakfast was included in the past but not now. Staff said that the name change and rebranding was meant to attract business people but there were no working outlets in the room and no usb or other charging outlets apart from one socket in the bathroom. Very inconvenient. The place was much nicer to stay at in the past 15 years but has been let down by its owners sadly.

Reviewed on Apr 14, 2026

The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $2,287

per person

Jun 9 - Jun 13

found 15 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

9.6/10 Exceptional! (515 reviews)

Five STAR! Amazing Hotel! Spa Perfecto! Lovely Stay!

Reviewed on Apr 16, 2026

c-hotels Joy

Historic Centre of Florence

CA $2,228

per person

May 24 - May 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9/10 Wonderful! (1,002 reviews)

Well located for the main train station and about a 15 minute walk to the Duomo. Friendly staff at all times. Comfortable room. Breakfast was free and okay.

Reviewed on Apr 4, 2026

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Santa Maria Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $994

CA $1,106 total

May 10 - May 11

includes taxes & fees

9.8/10 Exceptional! (229 reviews)

We really enjoyed the hotel, very clean, good atmosphere!!!

Reviewed on Apr 10, 2026

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI

CA $390

CA $435 total

Apr 26 - Apr 27

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

8.8/10 Excellent! (641 reviews)

The room was full of ants and other small insects. I was staying in the middle of Tuscany wine country, I would expect my room to have a corkscrew and at least glass glasses. The room only had flimsy plastic cups.

Reviewed on Apr 5, 2026

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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.