Healdsburg Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Healdsburg

H2Hotel
H2Hotel
4 out of 5
219 Healdsburg Ave, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is S$474 per night from 26 Mar to 27 Mar
S$474
includes taxes & fees
26 Mar - 27 Mar
9.4/10 Exceptional! (633 reviews)
"Great hotel !!! Closed to a lot of great wineries and restaurants."

Reviewed on 23 Mar,2025

H2Hotel
Montage Healdsburg
Montage Healdsburg
5 out of 5
100 Montage Way, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is S$1,125 per night from 20 Apr to 21 Apr
S$1,125
includes taxes & fees
20 Apr - 21 Apr
9.4/10 Exceptional! (90 reviews)
"Very romantic, great balconies with fire pits and they have an amazing Spa! 5stars!"

Reviewed on 17 Mar,2025

Montage Healdsburg
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 S$262 per night from 26 Mar to 27 Mar
S$262
includes taxes & fees
26 Mar - 27 Mar
8.8/10 Excellent! (251 reviews)
"Amazing amenities"

Reviewed on 22 Mar,2025

The Lodge at Healdsburg, Tapestry Collection by Hilton
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.

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.

What to do in Healdsburg

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

S$67
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

S$176
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
Welcome to Napa Valley!

Bicycle Guided Tour in Napa and Sonoma

S$266
per adult
Bicycle Guided Tour in Napa and Sonoma
See all activities in Healdsburg

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.