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Our top choices for Pienza romantic hotels

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
9.6 out of 10, Exceptional, (56)
"The owners and staff are hospitable .and accommodating very warm people "
Canada
aileen
Agriturismo Il Macchione

Podere Spedalone

Podere Spedalone
1.0 star property
Pienza
9.4 out of 10, Exceptional, (42)
"Amazing food, amazing views"
United States
Juan
Podere Spedalone

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 5.332.051 ₫
6.050.844 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

The Monteleone

The Monteleone
Monteleone d'Orvieto
9.8 out of 10, Exceptional, (8)
"“Oasi di pace in Umbria. Camera ampia, moderna e pulitissima; letto comodissimo e bagno con doccia top. Colazione ricca, con opzioni dolci e salate. Comodo il parcheggio interno e l’accesso semplice con codice. La piscina all’aperto è perfetta per rilassarsi dopo le visite nei borghi vicini. Staff gentilissimo (un grazie speciale ad Anna in reception) e massima cura dei dettagli. Siamo stati benissimo e torneremo sicuramente. Consigliatissimo!”"
Italy
matteo
The price is 2.782.423 ₫
3.060.666 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Monteleone

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 3.889.195 ₫
4.401.903 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Relais Villa Grazianella - UNA Esperienze

Grand Hotel Impero - Wellness & Exclusive SPA

Grand Hotel Impero - Wellness & Exclusive SPA
4.0 star property
Castel del Piano
9.2 out of 10, Wonderful, (82)
"One of my favourite hotels. I make it a special trip to stay there."
Canada
Andre
The price is 2.193.407 ₫
2.536.410 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Grand Hotel Impero - Wellness & Exclusive SPA

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (200)
"Great place to stay"
Canada
Robert
The price is 16.811.260 ₫
18.616.174 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Albergo San Biagio

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (131)
"Absolutely amazing resort with amazing staff and service. Great food and beautiful spa experience. Highly reccommend anyone going to Tuscany to book here - you will not be disappointed ! "
Canada
Megan
Capanna Suites
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.

Top Pienza Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Pienza?
Are you looking for a romantic holiday? If you want to explore the area, you might head to Palazzo Piccolomini, Historic Centre of Pienza or Pienza Cathedral. If you're interested in staying close to a certain attraction, you can sort properties by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Pienza?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Pienza: The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Pienza is 1065 mm.
What is there to do in Pienza?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Pienza. If you want to spend a day exploring, you might consider stopping at Palazzo Piccolomini, Historic Centre of Pienza or Pienza Cathedral.