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

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The Latest Val d'Elsa 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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Where to stay in Val d'Elsa

Find the best Val d'Elsa areas and neighborhoods for the activities you enjoy most. Learn more about Val d'Elsa

A historic square with stone buildings, a prominent tower, and outdoor seating areas.

San Gimignano City Centre

6 out of top 10 points of interest in this area

San Gimignano City Centre is noteworthy for its historic sites, and you can make a stop at top attractions like Piazza delle Erbe and Piazza Duomo.

A dilapidated brick structure with a chimney, surrounded by grass and trees.

Certaldo Alto

You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.

Pievescola

Travelers enjoy Pievescola for its restaurants and museums. Consider checking out Terre di Vini while you're in the area.

San Filippo

While there might not be top attractions in San Filippo, you can explore the larger area and discover places like Castello della Paneretta and Castello di Monsanto.

Mensano

When in Mensano, you can plan a visit to Terre di Vini and Archeological and Collegiate Church Museum, some noteworthy sights in the nearby area.

Stay near popular Val d'Elsa attractions

A historic square with a prominent tower, stone buildings, outdoor seating, and people walking.

Piazza della Cisterna

9.4/10 (327 reviews)

Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.

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A historic square with cobblestone pavement, a central fountain, and surrounding buildings with traditional architecture.

Monteriggioni Castle

9.0/10 (61 reviews)

After visiting Monteriggioni Castle, make a plan to see the other sights and activities in Monteriggioni. Discover the area's beautiful countryside, or seek out its local tours.

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A historic town with medieval towers and terraced vineyards.

San Gimignano Communal Palace

9.4/10 (150 reviews)

You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

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A historic stone building with a tall tower and arched windows.

Piazza Duomo

9.4/10 (295 reviews)

Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.

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Tenuta Torciano Winery

9.2/10 (40 reviews)

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.

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Medieval Criminal and Torture Museum

9.0/10 (66 reviews)

This intriguing museum highlights the callousness of humans via displays of authentic and gruesome torture devices from around the world.

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Vernaccia di San Gimignano Wine Museum

9.2/10 (15 reviews)

You can browse the exhibits at Vernaccia di San Gimignano Wine Museum, a museum with a storied past, during your travels to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

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Castello di Monsanto

6.0/10 (4 reviews)

You can enjoy a tasting or tour at Castello di Monsanto during your travels to Monsanto. Discover the beautiful countryside and wineries in this relaxing area.

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What to do in Val d'Elsa

Florence Day Trip: Medieval Villages & Cooking Class

$183

per adult

86% of travellers recommend

Tuscan Wine Tasting and Local Cheeses

$60

per adult

San Gimignano: Evening Flavors Dinner & Wine tasting

$65

per adult

See all activities in Val d'Elsa

Val d'Elsa Hotel Deals

Poderi Arcangelo

Localita Capezzano San Gimignano SI

Fully refundableReserve now, pay when you stay

$108 nightly

$125 total

Nov 8 - Nov 9

Total with taxes and fees

9/10 Wonderful! (379 reviews)

"Beautiful property, nice and helping staff. We enjoy our stay ."

Reviewed on Oct 1, 2026

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Fully refundableReserve now, pay when you stay

$68 nightly

$75 total

Nov 3 - Nov 4

Total with taxes and fees

8/10 Very Good! (371 reviews)

"Close to train station"

Reviewed on Oct 1, 2026

La Cisterna

Piazza Della Cisterna 23 San Gimignano SI

Fully refundableReserve now, pay when you stay

$87 nightly

$103 total

Nov 5 - Nov 6

Total with taxes and fees

9.2/10 Wonderful! (660 reviews)

"It was an okay stay for one night. Clean and a comfortable bed."

Reviewed on Oct 3, 2026

See all 3,314 properties in Val d'Elsa

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.