Val d'Orcia Vacation Packages 2026 from $1,109

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The Latest Val d'Orcia vacation packages

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

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$1,109

per person

Oct 24 - Oct 28

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (580 reviews)

Precise Tale Poggio Alla Sala

Save 100% on your flight

$2,224

per person

Oct 9 - Oct 15

found 5 hours ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

9.6/10 Exceptional! (156 reviews)

Horrible service at best. Not a 5 star hotel. Save your money.

Reviewed on Aug 17, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,504

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9/10 Wonderful! (1,006 reviews)

Hotel Villa Liana

Historic Centre of Florence

$1,349

per person

Oct 11 - Oct 17

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

8.8/10 Excellent! (360 reviews)

clean, spacious, well-stocked with toiletries and breakfast items too. walkable distance to all iconic sites. Grace, the breakfast host, did an incredible job, very welcoming & served with options for hot coffee drinks. All together, wonderful, memorable stay!!

Reviewed on May 23, 2026

Hotel Santa Croce

Historic Centre of Florence

$1,372

per person

Oct 11 - Oct 17

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

8.8/10 Excellent! (460 reviews)

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Stay near popular Val d'Orcia attractions

A historic church with a bell tower, arched windows, and a central dome.

Pienza Cathedral

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.

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Rolling green hills, a historic town with red-roofed buildings, and a prominent church tower.

Historic Centre of Pienza

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.

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Castello Banfi

9.4/10 (51 reviews)

This medieval estate blends Tuscan tradition with world-renowned winemaking excellence. Sample award-winning Brunello di Montalcino while overlooking rolling vineyards from the restored 18th-century village.

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Fortress of Montalcino

9.2/10 (54 reviews)

This pentagonal medieval stronghold was the final bastion of Siena's resistance against Medici conquest. Climb its historic ramparts for panoramic Tuscan views before sampling Brunello wines at the fortress enoteca.

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Tenuta Greppo Franco Biondi Santi

8.6/10 (8 reviews)

Birthplace of Italy's prestigious Brunello di Montalcino wine, Tenuta Greppo has defined excellence since 1888. Tour the historic cellars and vineyards where the Biondi-Santi family's winemaking traditions thrive.

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Abbazia di Sant'Antimo

9.6/10 (111 reviews)

This medieval Romanesque abbey offers a serene glimpse into monastic life amid Tuscan olive groves. Explore the intricate stone carvings and listen for occasional Gregorian chants echoing through its ancient walls.

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Castiglion del Bosco Winery

9.6/10 (5 reviews)

This historic estate, a founding consortium member, produces Italy's finest Brunello di Montalcino wines. Tour the vineyard and cellars before savoring wine pairings with local cheeses amid the Tuscan countryside.

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Palazzo Piccolomini

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.

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What to do in Val d'Orcia

Montalcino: Guided Winery Tour and Wine Tasting

$51

per adult

Seggiano: Guided Tour of the Olive Grove and Food Tasting

$28

per adult

Winery tour & wine tasting in Montalcino

$45

per adult

See all activities in Val d'Orcia

Val d'Orcia Hotel Deals

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Fully refundableReserve now, pay when you stay

$695 nightly

$776 total

Aug 30 - Aug 31

Total with taxes and fees

9/10 Wonderful! (367 reviews)

"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. ..."

Reviewed on Aug 14, 2026

Mastrojanni Relais - Small Luxury Hotels of the World

Localita Loreto e San Pio Montalcino SI

$487 nightly

$547 total

Aug 24 - Aug 25

Total with taxes and fees

9.8/10 Exceptional! (77 reviews)

"Perfect, pristine, could not be any better!"

Reviewed on Aug 6, 2026

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

10/10 Exceptional! (80 reviews)

"Best hotel ever."

Reviewed on Jul 27, 2026

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See all 636 properties in Val d'Orcia

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.