The Best Romantic Hotels in Pienza from ￥19,730 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 arch, wooden ceiling beams, a dining table, and bar stools.

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

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

1. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

￥17,759

￥21,666 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

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

Monticchiello

Melissa B.

￥15,823

￥19,730 total

includes taxes & fees

Oct 25 - Oct 26

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 bedroom with a wooden ceiling, a bed with white linens, a bedside table with a lamp, and a wooden shelf above the bed.

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

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

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

San Quirico d'Orcia

priscilla e.

￥14,385

￥22,731 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

A vintage-style room with a wooden table, a chair with a patterned cushion, a lantern with flowers, and a window with curtains.

4. Dragoncello Suite with four-poster bed

Montepulciano

Cari R.

￥26,639

￥26,639 total

includes taxes & fees

Oct 27 - Oct 28

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

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

A pool area with stone tiles, lounge chairs, and a wooden pergola.

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

5. 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.

￥99,628

￥114,545 total

includes taxes & fees

Oct 25 - Oct 26

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 white countertop, and a window with red curtains.

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

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.

￥19,180

￥36,584 total

includes taxes & fees

Oct 19 - Oct 20

A narrow stone alley with potted plants and benches.

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

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

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

7. The House of Alice, charm and relaxation

Montalcino (SI)

Robert S.

￥26,639

￥36,229 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 bedroom with a bed, bedside table, chair, dresser, and a window with a view.

8. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

￥17,759

￥25,217 total

includes taxes & fees

Oct 21 - Oct 22

View all properties

Top Pienza Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"This was an amazing stay recommended by a friend and we really loved this place. The only immediate issues were the A/C broke and the TV was hard to setup, and the toilet seat was cracked and broke when I sat on it. But they fixed all that on day 1 and we had an amazing time - staff was amazing, grounds, parking, quiet, romantic, everything. The restaurant was amazing wine cellar. The food a little exotic so if you want more basic - then head over to Cortona with a car 15 min drive up the hill. Best part of trip was having a car. The people amazing, Daniel, Enrico, and cant remember everyone - everyone was amazing."

Hotel Corsignano

10/10 Excellent

"Our stay at the Corsignano in Pienza was perfect. Everything here was top notch and I would definitely stay here again and recommend this place to anyone. Pienza was the perfect home base to take day trips and see Tuscany. Loved the Instagram video that helped us find the spot where Gladiator was taped!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"La vue est panoramique et le château est grandiose"

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."

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

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