Healdsburg Holidays

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Healdsburg Holiday

Our pick of the best Healdsburg Hotel Deals

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

198 Dry Creek Road Healdsburg CA
Fully refundableReserve now, pay when you stay
NZ$215
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,013 reviews)
"Close enough to downtown that I walked via a lovely path, but far enough away from the crowds/noise. Nice little pool. Would definitely stay there again!!"

Reviewed on 7 Sept 2026

Dry Creek Inn MOD Collection by Sonesta
Appellation Healdsburg

Appellation Healdsburg

101 Dovetail Ln Healdsburg CA
Fully refundableReserve now, pay when you stay
NZ$843
15 Sept - 16 Sept
includes taxes & fees
Appellation Healdsburg
The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

1261 Grove St Healdsburg CA
NZ$294
8 Sept - 9 Sept
includes taxes & fees
The Lodge at Healdsburg, Tapestry Collection by Hilton
See all 500 properties in Healdsburg
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.

Stay near popular Healdsburg attractions

Dry Creek Vineyard

9.4/10 (126 reviews)
Historic Dry Creek Vineyard pioneered Sauvignon Blanc planting in the region after Prohibition. Enjoy private seated tastings amid Loire Valley-inspired grounds perfect for an afternoon picnic.
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Healdsburg Plaza

9.4/10 (657 reviews)
This historic 1850s town square serves as Healdsburg's cultural heart, surrounded by wine tasting rooms and shops. Relax under mature trees or enjoy the central gazebo while experiencing quintessential Wine Country charm.
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Jordan Vineyard & Winery

10.0/10 (11 reviews)
This French-inspired estate winery crafts elegant Cabernet Sauvignon and Chardonnay in Alexander Valley's picturesque landscape. Enjoy seated tastings paired with seasonal hors d'oeuvres from the estate gardens.
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Mazzocco Winery

8.6/10 (24 reviews)
Renowned for its single-vineyard Zinfandels that showcase Dry Creek Valley's diverse terroir. Savour a personalised tasting on the outdoor patio with panoramic vineyard views, best enjoyed in spring or fall.
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Ridge Vineyards - Lytton Springs

Ridge Lytton Springs crafts exceptional Zinfandel from 115-year-old vines in Sonoma's Dry Creek Valley. Enjoy seated tastings overlooking historic vineyards in their eco-sustainable winery.
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SingleThread Farm at Dry Creek

This three-Michelin-starred farm-restaurant showcases ingredients grown on its own 24-acre property in Healdsburg. Experience their seasonal tasting menu that transforms local harvests into culinary masterpieces.
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Chalk Hill Estate Vineyard

8.4/10 (12 reviews)
This 1,300-acre estate showcases premium wines amidst rolling Sonoma vineyards and culinary gardens. Reserve the Hummer Estate Tour to explore hidden corners while sampling their acclaimed Estate Chardonnay.
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Healdsburg Center for the Arts

8.8/10 (28 reviews)
Take the family on an outing to Healdsburg Center for the Arts during your trip to Healdsburg. Stroll along the area's riverfront or simply savour its wineries.
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What to do in Healdsburg

Sonoma County Self-Guided Wine Tour: GPS Audio Driving Guide

Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide

NZ$50
per traveller
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

NZ$84
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Napa Valley Self-Guided Wine Tour: GPS Audio Driving Guide

Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide

NZ$67
per traveller
Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide
See all activities in Healdsburg

Frequently asked questions

How much does a Healdsburg holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Healdsburg costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Healdsburg?
December, January and February are the best times to look for cheap Healdsburg holiday packages. Travelling in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Healdsburg?
With a well-organised itinerary, you can easily hit the most popular Healdsburg attractions in a handful of days. But if you want to explore off the beaten track or go on day tours, consider booking your Healdsburg holiday for longer.
Is it worth booking a holiday package to Healdsburg?
It's no wonder a Healdsburg holiday is on the to-do list of many travellers. Major attractions like Healdsburg Plaza are just the beginning of what you can explore here.
How to find the best Healdsburg package deals?
Finding a cheap Healdsburg package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Healdsburg package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Healdsburg holiday as a package?
You can enjoy significant savings on your next Healdsburg getaway by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Healdsburg?
If you have your Healdsburg travel dates confirmed, book early to grab some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Healdsburg?
  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Healdsburg.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodation will likely be the largest expense during your trip to Healdsburg.
  3. Determine how many days away: Start by making a list of all the activities and attractions you'd like to experience in Healdsburg. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Healdsburg holiday package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.