The Best Romantic Hotels in Pienza from ￥19,700 in 2026

A historic square with a prominent tower and statues.

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Our top choices for Pienza romantic hotels

A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

A kitchen with a brick archway, two bar stools, a countertop, and a hanging light fixture.

A stone building with a staircase leading to a door, surrounded by a hedge and a cobblestone ground.

A bedroom with a large bed, a wooden ceiling, a mirror, a bicycle, and a chair.

1. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

￥17,663

￥21,549 total

includes taxes & fees

Oct 29 - Oct 30

A bedroom with a bed, a desk, and a chair. There is a wooden ceiling and a window.

A narrow stone pathway leading to a wooden door, surrounded by greenery and a metal railing.

A stone building with a staircase leading to a door, a small balcony, and a street in front.

A kitchen with white cabinets, a tiled backsplash, and a wooden ceiling.

2. The house in the village - Angelica apartment - Vald'Orcia

Monticchiello

Melissa B.

￥15,799

￥19,700 total

includes taxes & fees

Oct 18 - Oct 19

A two-story building with a stone facade, a wooden door, and shutters on the windows. There are potted plants in front of the entrance.

A rustic room with a wooden barrel table, a lamp, a book, and a bed in the background.

A wooden dining table set with plates, glasses, and a bottle of wine, with a window and wooden wall in the background.

A stone bench with snow on it, overlooking a snow-covered landscape with buildings and trees.

3. SUITE WINE - Relax & Design in the Heart of the Valdorcia

San Quirico d'Orcia

priscilla e.

￥15,896

￥24,198 total

includes taxes & fees

Nov 5 - Nov 6

A stone-walled patio with wicker furniture, a table, and a view of a green landscape.

A stone house with a tiled roof, a covered patio, and a gravel driveway.

A room with a sliding glass door leading to an outdoor area with a stone wall and trees.

A bedroom with a large bed, a wooden headboard, a white nightstand, a bedside lamp, and a wardrobe with a rustic finish.

4. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

"Incredible stay! Property was beautifully restored and outfitted, and immaculately clean when we arrived. The host was very responsive, helping us bring in a local chef and responded quickly to our various questions during our stay. The heated pool was wonderful. The property was the right size for seven guests. We hope to return because six nights here wasn’t enough! I wish there was an option to give higher than five stars!"

Marshall W.

￥99,087

￥113,924 total

includes taxes & fees

Oct 25 - Oct 26

A bedroom with a four-poster bed, a bench, a chandelier, and a window with curtains.

A room with a wooden dining table, a chair, a small cabinet, a mirror, and a wall-mounted light fixture.

A wooden chest with a white interior, a coffee cup, pastries, a flower pot, and a salt shaker.

A shower with a glass door, a wooden ceiling, and a tiled wall.

5. Dragoncello Suite with four-poster bed

Montepulciano

Cari R.

￥26,494

￥26,494 total

includes taxes & fees

Oct 28 - Oct 29

A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

A stone patio with a round table and chairs, surrounded by lush greenery and potted plants.

A modern kitchen with grey cabinets, a central island, and a dining area with clear chairs.

A modern kitchen with grey cabinets, a white countertop, and a window with red curtains.

6. Romantic farm in the Sienese hills

Trequanda, Siena

"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...

Harald B.

￥19,076

￥36,385 total

includes taxes & fees

Oct 29 - Oct 30

A narrow stone alley with potted plants and benches.

A rustic kitchen with stone walls, wooden beams, a bar area with stools, and a small table with kitchenware and flowers.

A rustic room with a stone wall, a fireplace, a white sofa, and a wooden bench.

A bedroom with stone walls, a wooden ceiling, a bed with a quilt, a bedside table with a lamp, and a window.

7. The House of Alice, charm and relaxation

Montalcino (SI)

Robert S.

￥26,494

￥36,032 total

includes taxes & fees

Nov 1 - Nov 2

A stone building with a sign reading "Borgo di Mezzo".

A modern living room with a white sofa, a white chair, a small round table, and a bookshelf.

A bathroom with a white sink, a mirror, and a vase with purple flowers. There are two bottles of soap on a tray.

A dining area with a wooden table, two chairs, a vase with flowers, a candle holder, and a fireplace.

8. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

￥17,663

￥25,082 total

includes taxes & fees

Oct 21 - Oct 22

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Top Pienza Hotel Reviews

Hotel Villa Ricci

8/10 Good

"Bien situe Bon déjeuner"

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent

"Our third stay here. It’s so nice. The town is also quaint too."

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."

Frequently asked questions

Searching for romantic hotels in Pienza?

Are you and your partner in need of a romantic getaway? 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 by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.

What's the best accommodation for a romantic getaway to Pienza?

House with private pool with beautiful view Val d 'Orcia is a favorite country house for couples, and features private pools and free WiFi.

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, check out these details about year-round temperatures in Pienza: The hottest months are usually August and July with an average temp of 69°F, while the coldest months are January and February with an average of 42°F. Average annual precipitation for Pienza is 42 inches.

What is there to do in Pienza?

There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Pienza. If you want to spend a day exploring, you might consider a stop at Palazzo Piccolomini, Historic Centre of Pienza, or Pienza Cathedral.

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Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pienza Romantic Hotels

Our top choices for Pienza romantic hotels

1. "Il Focolare" Superior Apartment in Monticchiello

2. The house in the village - Angelica apartment - Vald'Orcia