--- title: "Pienza Romantic Vacations 2026 | Expedia" description: "Find incredible offers on Pienza Romantic Vacations! Plan your next Romantic trip today with Expedia." canonical: "https://www.expedia.com/lp/theme-vacations/romantic-vacations/6023645/Pienza" language: en-US market: US currency: USD prices_as_of: 2026-11-13T22:24:43Z --- # Pienza Romantic Vacations ![A historic square with a prominent tower and statues.](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Romantic vacation packages in Pienza Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A hotel room with two beds, each with white linens and pillows, and a dark wood panel wall.](https://images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/3c6602ae.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern restaurant with green chairs and white tables, large windows, and a dark wooden floor.](https://images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/75d8788b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 10** ### [Aurum Firenze + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-04/2027-02-10/?FromAirport=EWR&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=28961941&dealMarker=&paandie=true&cabinClass=e) Historic Centre of Florence 5 nights **7.4/10** \- Good (1,001 reviews) "Nice place, good location" Reviewed November 11, 2026 Roundtrip • New York (EWR) - Florence (FLR) EWR - FLR • 1 stop FLR - EWR • 1 stop [~~$1,353~~](https://www.expedia.com/) **$995** per traveler found 2 days ago - ![A rooftop pool with a view of the Florence Cathedral and surrounding cityscape.](https://images.trvl-media.com/lodging/32000000/31160000/31158000/31157955/33d9bf6e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A table set for two with a bottle of wine, two glasses, a rose, and a plate, overlooking a historic building.](https://images.trvl-media.com/lodging/32000000/31160000/31158000/31157955/a50f3f41.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 10** ### [Donati Luxury Tower Suites + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-04/2027-02-10/?FromAirport=EWR&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=31157955&dealMarker=&paandie=true&cabinClass=e) Historic Centre of Florence 5 nights **9.8/10** \- Exceptional (83 reviews) "Great boutique hotel with good size room and bathroom. Very clean and helpful staff. Would definitely stay here again." Reviewed November 9, 2026 Roundtrip • New York (EWR) - Florence (FLR) EWR - FLR • 1 stop FLR - EWR • 1 stop [~~$2,754~~](https://www.expedia.com/) **$1,916** per traveler found 2 days ago - ![A hotel room with a bed, a flat-screen TV mounted on the wall, a wooden wardrobe, and a mirror.](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/4fb74083.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A view of a building's exterior with a wooden door and a window, surrounded by greenery.](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/c67c8bb8.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 10** ### [Aurum Uffizi + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-04/2027-02-10/?FromAirport=EWR&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2541615&dealMarker=&paandie=true&cabinClass=e) Historic Centre of Florence 5 nights **7.6/10** \- Good (1,001 reviews) Roundtrip • New York (EWR) - Florence (FLR) EWR - FLR • 1 stop FLR - EWR • 1 stop [~~$1,481~~](https://www.expedia.com/) **$1,040** per traveler found 2 days ago - ![A table set for two with wine glasses, a candle, and cutlery, overlooking a river with buildings and a bridge in the background.](https://images.trvl-media.com/lodging/1000000/20000/14600/14583/9c1dd8be.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern living room with a view of a cityscape through large windows.](https://images.trvl-media.com/lodging/1000000/20000/14600/14583/a7c94f06.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 22 - Jan 29** ### [Hotel Lungarno - Lungarno Collection + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-22/2027-01-29/?FromAirport=BOS&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14583&dealMarker=&paandie=true&cabinClass=e) Historic Centre of Florence 4 nights **9.6/10** \- Exceptional (648 reviews) "Overall, the property is beautiful, very centrally, located and easy walking distance to every place. Our room was lovely very clean and the staff very helpful. I would definitely stay here again." Reviewed November 10, 2026 Roundtrip • Boston (BOS) - Florence (FLR) BOS - FLR • 1 stop FLR - BOS • 1 stop [~~$1,812~~](https://www.expedia.com/) **$1,336** per traveler found 2 days ago - ![A courtyard with outdoor seating and a building with arched windows.](https://images.trvl-media.com/lodging/1000000/10000/1300/1230/53bb1d8b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A nighttime view of a courtyard with a paved path, surrounded by buildings and trees.](https://images.trvl-media.com/lodging/1000000/10000/1300/1230/ea04c208.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 10** ### [Palazzo Monnalisa + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-04/2027-02-10/?FromAirport=EWR&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1230&dealMarker=&paandie=true&cabinClass=e) Historic Centre of Florence 5 nights **9.0/10** \- Wonderful (817 reviews) Roundtrip • New York (EWR) - Florence (FLR) EWR - FLR • 1 stop FLR - EWR • 1 stop [~~$2,137~~](https://www.expedia.com/) **$1,602** per traveler found 2 days ago ## Discover the most popular places to visit in Pienza ### Pienza Cathedral ![A historic church with a bell tower, arched windows, and a central dome.](https://images.trvl-media.com/place/6105122/e20d799b-4862-43ea-9619-5002538cee2b.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 9.4/10 (460 reviews) Pope Pius II's Renaissance masterpiece showcases harmonious Gothic elements and luminous three-nave design. Arrive early to admire the 15th-century Sienese paintings and enjoy panoramic Tuscan views from the corridor. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=6105122) ### Historic Centre of Pienza ![Rolling green hills, a historic town with red-roofed buildings, and a prominent church tower.](https://images.trvl-media.com/place/623288508983611392/1c80f999-00d7-4d2d-a82d-92a947ff3f82.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 9.6/10 (42 reviews) Pienza's Historic Centre showcases Pope Pius II's Renaissance ideal city vision with harmonious architecture. Explore cobblestone streets, the Cathedral and Palazzo Piccolomini, and sample the town's famous pecorino cheese. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=623288508983611392) ### Palazzo Piccolomini Rating: 9.4/10 (199 reviews) This Renaissance masterpiece was Pope Pius II's summer residence, designed by Bernardo Rossellino. From its hanging gardens, savor breathtaking panoramic views across the Val d'Orcia's rolling Tuscan landscape. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=6105120) ### Monastery of Sant'Anna in Camprena This former monastery in the Tuscan hills showcases remarkable Renaissance frescoes in a tranquil setting. Savor authentic regional cuisine while staying overnight in the historic stone buildings. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=811545272430104576) ### Piazza Pio II Rating: 9.2/10 (44 reviews) This Renaissance masterpiece, designed by Bernardo Rossellino in 1459, showcases perfect architectural harmony at Pienza's heart. Explore the cathedral's artworks and enjoy sweeping Tuscan views from the elegant terrace. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=553248621533000907) ### Palazzo Vescovile Rating: 9.0/10 (12 reviews) The Palazzo Vescovile showcases a captivating collection of religious art from the 14th-15th centuries. Admire Pietro Lorenzetti's Madonna di Monticchiello while exploring eleven rooms filled with sacred treasures. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=553248621533000905) ### Palazzo Borgia Rating: 8.8/10 (21 reviews) This Renaissance palace houses the Museo Diocesano with masterpieces by Lorenzetti and Signorelli. Admire 12th-century crucifixes and medieval art while exploring the former residence of Cardinal Rodrigo Borgia. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=6105116) ### Palazzo Comunale Rating: 9.0/10 (24 reviews) After visiting Palazzo Comunale, make a plan to see the other sights and activities in Pienza. While you're here, you can savor the wineries. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=romantic®ionId=6105118) ### What to do in Pienza ![Tasting Tour in One of The Most Beautiful Cellars in the World](https://mediaim.expedia.com/localexpert/1175608/57fdcc57-4a4e-4904-bd65-7afb578cabbc.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Tasting Tour in One of The Most Beautiful Cellars in the World](https://www.expedia.com/things-to-do/a.a1175608.activity-details?rid=6023645) $37 per adult 100% of travelers recommend ![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Montepulciano Wine Tasting in the Tuscan Countryside](https://www.expedia.com/things-to-do/a.a50286653.activity-details?rid=6023645) $28 per adult 0% of travelers recommend ![Montepulciano: Winery Tour and Tasting](https://mediaim.expedia.com/localexpert/4538591/6682c7c0-1063-439a-bfd8-e34ae98bf836.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Montepulciano: Winery Tour and Tasting](https://www.expedia.com/things-to-do/a.a4538591.activity-details?rid=6023645) $39 per adult 100% of travelers recommend [See all activities in Pienza](https://www.expedia.com/things-to-do/search?rid=6023645) ## Top Romantic Pienza Hotels ### [Hotel Corsignano](https://www.expedia.com/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Two people sitting at a round table outdoors with a scenic view of mountains in the background.](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/ba2de8ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Via Della Madonnina 11, Pienza, SI, 53026, IT - Location: 0.2 mi from Pienza - Star rating: 4/5 - Guest rating: 9.4/10 (Exceptional, 400 reviews) - Price: $128 nightly, $148 total, Nov 15 - Nov 16, Total with taxes and fees, for Top Romantic Pienza Hotels ### [Hotel San Gregorio](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![A table set outdoors with breakfast items including bread, a cup, and a glass of juice.](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Via Della Madonnina 4, Pienza, SI, 53026, IT - Location: 0.1 mi from Pienza - Star rating: 3/5 - Guest rating: 9.4/10 (Exceptional, 172 reviews) - Price: $135 nightly, $155 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Romantic Pienza Hotels ### [Rossellino](https://www.expedia.com/Pienza-Hotels-Rossellino.h5065554.Hotel-Information) ![A narrow alleyway with stone walls and a brick floor, leading to a building with windows and balconies.](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/98d42f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Corso Rossellino 97, Pienza, SI, 53026, IT - Location: < 0.1 mi from Pienza - Guest rating: 8.6/10 (Excellent, 70 reviews) - Price: $113 nightly, $129 total, Nov 20 - Nov 21, Total with taxes and fees, for Top Romantic Pienza Hotels ### [PienzaLettings Suites](https://www.expedia.com/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information) ![A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/4f1f04f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Piazza S. Carlo 4, Pienza, SI, 53026, IT - Location: 0.1 mi from Pienza - Guest rating: 10/10 (Exceptional, 7 reviews) - Price: $83 nightly, $96 total, Dec 13 - Dec 14, Total with taxes and fees, for Top Romantic Pienza Hotels - Review: Great locat ### [Casa Gioia - Casa Olivieri](https://www.expedia.com/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information) ![A stone building with a wooden door, a staircase, and a small window with a metal grill.](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1589x0y0-ab9335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Corso il Rossellino 91, Pienza, SI, 53026, IT - Location: < 0.1 mi from Pienza - Guest rating: 10/10 (Exceptional, 3 reviews) - Price: $81 nightly, $94 total, Dec 9 - Dec 10, Total with taxes and fees, for Top Romantic Pienza Hotels - Review: Location was in the middle of the ZTL in Pienza which means you get to walk out of your room into the middle of the touristy part of the city with no cars to really worry about most of the time. Parking was about a 10 min walk away so it wasn't too bag to walk with bags. Cute suite we had with a kitchen and dining room. Had A/C in all rooms but we only used the one in the bedroom. Cute and convenient accommodation in a great location. ### [Podere Spedalone](https://www.expedia.com/Pienza-Hotels-Podere-Spedalone.h34836233.Hotel-Information) ![An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/3ffbc3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Strada per Cosona SP71, Pienza, SI, 53026, IT - Location: 3.9 mi from Pienza - Star rating: 1/5 - Guest rating: 9/10 (Wonderful, 54 reviews) - Price: $146 nightly, $165 total, Nov 15 - Nov 16, Total with taxes and fees, for Top Romantic Pienza Hotels - Review: The common areas could be cleaner. ### [La Bandita Townhouse](https://www.expedia.com/Pienza-Hotels-La-Bandita-Townhouse.h5598434.Hotel-Information) ![An outdoor dining area with wooden tables and benches, stone walls, and greenery.](https://images.trvl-media.com/lodging/6000000/5600000/5598500/5598434/27c3f06b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 111 Corso Rossellino, Pienza, SI, 53026, IT - Location: 0.1 mi from Pienza - Guest rating: 9.6/10 (Exceptional, 17 reviews) - Price: $447 nightly, $497 total, Nov 14 - Nov 15, Total with taxes and fees, for Top Romantic Pienza Hotels - Review: Fantastic venue! Loved Pienza! The Inn was beautiful and the staff extremely friendly and welcoming. We would love to go back ### ["Il Focolare" Superior Apartment in Monticchiello](https://www.expedia.com/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information) ![A kitchen with a granite countertop, a hanging pendant light, and a brick archway.](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/6e91d9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Monticchiello, Toscana, IT - Location: 2.4 mi from Pienza - Guest rating: 10/10 (Exceptional, 12 reviews) - Price: $123 nightly, $127 total, Nov 19 - Nov 20, Total with taxes and fees, for Top Romantic Pienza Hotels - Review: "Nous avons adoré notre séjour dans ce petit village médiéval très tranquille. La vue sur la vallée est splendide et le coucher de soleil magnifique. La maison est parfaite sauf peut être le manque d'insonorisation: nous entendions très bien les voisins du dessus avec leur bébé très tôt le matin... Il faut aussi savoir que le stationnement de trouve en bas d'une côte avant d'arriver aux portes du village et qu'il reste encore une côte à gravir des portes jusqu'à la maison. Pour nous, c'était ok,... 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. [See all properties in Pienza](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28®ionId=6023645&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## How to find a romantic Pienza vacation ### How can I find the best Pienza vacation packages for couples? To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing. ### How can I find cheap Pienza romantic packages for two? For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering. ### How can I plan a great romantic trip to Pienza? Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two. ### How much is a trip for two to Pienza? Put a price on love with stunning deals for duos starting at just $995\. Prices and availability are subject to change. Additional terms may apply. ### Can I book Pienza spa packages for couples? Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match. ### How can I book romantic weekend getaway packages in Pienza? To book a loved-up break in Pienza, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation). ### Can I book a romantic trip to Pienza with free cancellation and/or flexible dates? The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options. ### Why should I book my Pienza romantic holiday with Expedia? If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?