Healdsburg Vacations

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Find the Best Healdsburg Vacation Packages

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
Fully refundableReserve now, pay when you stay
The price is NT$4,447 per night from Sep 1 to Sep 2
NT$4,447
NT$5,167 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (307 reviews)
We love Healdsburg
"The bed was very comfortable, the shower was huge, in a good way, and the wine was delicious"

Reviewed on 2025/8/1

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 NT$25,367 per night from Sep 1 to Sep 2
NT$25,367
NT$32,148 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (102 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 2025/6/1

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 NT$3,864 per night from Sep 1 to Sep 2
NT$3,864
NT$4,490 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"It was close to everything and it was incredibly safe"

Reviewed on 2025/8/4

Best Western Dry Creek Inn
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.

Discover the most popular places to visit in Healdsburg

It’s barrel tasting weekend here along the wine road.

Mazzocco Winery

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

Mazzocco Winery

Healdsburg Plaza

Find out about the history of Healdsburg with a stop at Healdsburg Plaza. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Healdsburg Plaza

Healdsburg Museum

You can spend time browsing the exhibits at Healdsburg Museum during your travels in Healdsburg. Amble around this family-friendly area's riverfront and enjoy its wineries.

Healdsburg Museum

Frequently asked questions

How much does a Healdsburg vacation package cost?
You can grab a vacation package to this popular destination on Expedia. But how much your vacation 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 vacation packages. Traveling 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-organized 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 vacation for longer.
Is it worth booking a vacation package to Healdsburg?
It's no wonder a Healdsburg vacation is on the to-do list of many travelers. 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 vacation as a package?
You can enjoy significant savings on your next Healdsburg getaway by booking a personalized vacation 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 vacation 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 accommodations 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 vacation 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.