Healdsburg Holidays

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Healdsburg Holiday

Our pick of the best Healdsburg Hotel Deals

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

3.5 out of 5
1261 Grove St, Healdsburg, CA
The price is NZ$329 per night from 12 Aug to 13 Aug
NZ$329
12 Aug - 13 Aug
includes taxes & fees
8.8/10 Excellent! (299 reviews)
"Just minutes from downtown. They do charge for parking $10 and bottle water $1We liked it and would stay again."

Reviewed on 16 Jul. 2025

The Lodge at Healdsburg, Tapestry Collection by Hilton
Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is NZ$1,805 per night from 17 Aug to 18 Aug
NZ$1,805
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (100 reviews)
"The Montage is such a stunning and blissful place to stay in wine country! The service and people were always very nice. Upon arrival, they greeted us with a "splash" of welcome wine and drove us to our room via golf cart. The rooms are beautifully appointed...ours had a vineyard view with a fire ..."

Reviewed on 1 Jun. 2025

Montage Healdsburg
Best Western Dry Creek Inn

Best Western Dry Creek Inn

3 out of 5
198 Dry Creek Rd, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 27 July to 28 July
NZ$272
27 July - 28 July
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"Great cleaning lady!"

Reviewed on 20 Jul. 2025

Best Western Dry Creek Inn
See all 513 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.

Discover the most popular places to visit in Healdsburg

Dry Creek Vineyard which includes flowers

Dry Creek Vineyard

Choose from the range of informative and intriguing tours and try the acclaimed brand known as the Wine for Sailors.

Dry Creek Vineyard

Wilson Winery

You can enjoy a tasting or tour at Wilson Winery during your travels to Healdsburg. Visit the wineries or top-notch restaurants in this walkable area.

Wilson Winery

Healdsburg Center for the Arts

Healdsburg Center for the Arts is just one of the places to see in Healdsburg, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.

Healdsburg Center for the Arts

What to do in Healdsburg

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

NZ$83
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

NZ$232
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
Ride

Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

NZ$447
per adult
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
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.

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