Val d'Orcia Vacation Packages 2026 from $1,024

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The Latest Val d'Orcia vacation packages

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

Dimora Palanca Boutique & SPA

Historic Centre of Florence

$1,024

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (75 reviews)

Hotel Duomo Firenze

Historic Centre of Florence

$1,033

per person

Dec 10 - Dec 16

found 22 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (1,000 reviews)

Absolutely everything was perfect - from checkin to deprture- Gelato and cookies available all day, wonderful breakfast, room was SO Awesome facing the Duomo, assist to schedule a taxi - lift so less stairs - would absolutely recommend !!!

Reviewed on Oct 2, 2026

Donati Luxury Tower Suites

Historic Centre of Florence

$1,536

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.8/10 Exceptional! (77 reviews)

Excellent lodging option very close to the Duomo and central to Florence. It is a terrific location in that it is close to everything but secluded off a very small road that only gets traffic for people checking in or leaving the property. The lodging is in a very old tower that has been converted to about 10 rooms. The front desk is excellent and surprised us when we checked in by telling us they would deliver an assortment of pastries to our room every day for breakfast. We had the Gemma suite which was not large but well laid out with a very comfortable bed and furniture and a very nice bathroom.

Reviewed on Oct 4, 2026

Portrait Firenze - Lungarno Collection

Historic Centre of Florence

Save 100% on your flight

$2,206

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.8/10 Exceptional! (318 reviews)

We couldn’t have had a more enjoyable day at this fabulous hotel. The staff responded to our every whim and even anticipated some! And its location right in the center of historic Florence cannot be beat. We will be back again!

Reviewed on Oct 4, 2026

Monastero di Cortona Hotel & Spa

Cortona Old Town

$1,292

per person

Dec 12 - Dec 18

found 17 hours ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

10/10 Exceptional! (337 reviews)

Beautiful experience. Would recommend again and again.

Reviewed on Oct 6, 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

$1,820 nightly

$2,013 total

Oct 18 - Oct 19

Total with taxes and fees

10/10 Exceptional! (83 reviews)

"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside ..."

Reviewed on Oct 4, 2026

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Fully refundableReserve now, pay when you stay

$552 nightly

$619 total

Nov 4 - Nov 5

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

Corte Francigena - Apartments

Via Ferretti Montalcino SI

Fully refundableReserve now, pay when you stay

$98 nightly

$116 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

See all 640 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.