Healdsburg Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Healdsburg

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 €121 per night from 3 Aug to 4 Aug
€121
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very good! (1,015 reviews)
"We were gone all day and came back to our door not opening...Maintenance was called and quickly came and fixed the issue. The AC wasn't wonderful---very stuffy in the room."

Reviewed on 11 Jul 2026

Dry Creek Inn MOD Collection by Sonesta
H2Hotel

H2Hotel

4 out of 5
219 Healdsburg Ave Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is €319 per night from 26 Jul to 27 Jul
€319
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (765 reviews)
"Clean, unique, in the middle of town. Love it."

Reviewed on 5 Jul 2026

H2Hotel
Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is €844 per night from 3 Aug to 4 Aug
€844
3 Aug - 4 Aug
includes taxes & fees
9.6/10 Exceptional! (134 reviews)
"My daughters and I spent three glorious nights having incredible spa treatments and marvelous food. The only downside was the extremely uncomfortable bed."

Reviewed on 24 Mar 2026

Montage Healdsburg
See all 511 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

Shopping in Healdsburg

History Walking Tour of Healdsburg

€39
per adult
History Walking Tour of Healdsburg
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

€43
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Kayaking at the Coast!

Russian River Kayak Tour at the Beautiful Sonoma Coast

€116
per adult
100% of travellers recommend
Russian River Kayak Tour at the Beautiful Sonoma Coast
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.

Explore a world of travel with Expedia

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