Val d'Orcia Vacation Packages 2026 from $1,069

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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

$1,069

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (605 reviews)

Well kept

Reviewed on Oct 8, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$2,185

per person

Dec 28 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9/10 Wonderful! (1,002 reviews)

Hotel La Scaletta exceeded our expectations! Everything about the property - location, amenities, breakfast, room, and helpful staff - was excellent. I had stayed in the hotel (and loved it) decades before but it has ascended from a pensione to a true hotel. I hope to return one day!

Reviewed on Oct 2, 2026

Aurum Uffizi

Historic Centre of Florence

$1,581

per person

Dec 26 - Jan 1

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

7.6/10 Good! (1,003 reviews)

Aurum Firenze

Historic Centre of Florence

$1,497

per person

Dec 26 - Jan 1

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

7.4/10 Good! (1,015 reviews)

My favorite place to stay in Florence! The staff is awesome clean rooms the breakfast is pretty good as well! Definitely book here if you was to stay in the heart of Florence!

Reviewed on Oct 8, 2026

Grand Hotel Cavour

Historic Centre of Florence

$2,518

per person

Dec 28 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.4/10 Exceptional! (1,000 reviews)

Staff was friendly and accommodating! Rooms were very clean and SPACIOUS! Would definitely return!

Reviewed on Oct 5, 2026

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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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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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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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What to do in Val d'Orcia

Montalcino: Guided Winery Tour and Wine Tasting

$52

per adult

Seggiano: Guided Tour of the Olive Grove and Food Tasting

$52

per adult

Winery tour & wine tasting in Montalcino

$46

per adult

See all activities in Val d'Orcia

Val d'Orcia Hotel Deals

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

Fully refundableReserve now, pay when you stay

$1,790 nightly

$1,980 total

Oct 18 - Oct 19

Total with taxes and fees

10/10 Exceptional! (84 reviews)

"Nice and quiet excellent hospitality"

Reviewed on Oct 6, 2026

Corte Francigena - Apartments

Via Ferretti Montalcino SI

Fully refundableReserve now, pay when you stay

$96 nightly

$115 total

Nov 2 - Nov 3

Total with taxes and fees

9.8/10 Exceptional! (19 reviews)

"The unit is very clean, awesome breakfast, beautiful view"

Reviewed on Sep 24, 2026

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Fully refundableReserve now, pay when you stay

$545 nightly

$611 total

Nov 8 - Nov 9

Total with taxes and fees

9/10 Wonderful! (377 reviews)

"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."

Reviewed on Sep 27, 2026

See all 644 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.