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

3 out of 5
198 Dry Creek Road Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is NZ$258 per night from 27 July to 28 July
NZ$258
27 July - 28 July
includes taxes & fees
Dry Creek Inn MOD Collection by Sonesta
Appellation Healdsburg

Appellation Healdsburg

4.5 out of 5
101 Dovetail Ln Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is NZ$778 per night from 26 July to 27 July
NZ$778
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (109 reviews)
"The property is beautiful! Multiple restaurants and bars and pools. Great rooms with super comfy beds and the staff are all super friendly! We had booked for one night but ended up staying more and making it the hub for the vacation"

Reviewed on 21 July 2026

Appellation Healdsburg
Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is NZ$1,854 per night from 4 Aug to 5 Aug
NZ$1,854
4 Aug - 5 Aug
includes taxes & fees
9.6/10 Exceptional! (136 reviews)
"Gorgeous property, first class experience."

Reviewed on 18 July 2026

Montage Healdsburg
See all 508 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.
See properties

What to do in Healdsburg

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

NZ$88
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Shopping in Healdsburg

History Walking Tour of Healdsburg

NZ$79
per adult
History Walking Tour of Healdsburg
Dutton-Goldfield Winery: Pinot Noir Tasting

Dutton-Goldfield Winery: Pinot Noir Tasting

NZ$97
per adult
Dutton-Goldfield Winery: Pinot Noir Tasting
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.