Healdsburg Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SAR 390 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

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Find the Best Healdsburg Vacation Packages

Healdsburg Hotel Deals

Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is SAR 2,401 per night from Dec 18 to Dec 19
SAR 2,401
SAR 3,045 total
18 Dec - 19 Dec
includes taxes & fees
9.4/10 Exceptional! (113 reviews)
Everything was amazing. Hands down the best customer service we have ever had.

Reviewed on 7 November 2025

Montage Healdsburg
Appellation Healdsburg

Appellation Healdsburg

4.5 out of 5
101 Dovetail Ln Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is SAR 913 per night from Nov 30 to Dec 1
SAR 913
SAR 1,323 total
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (25 reviews)
Service and property was amazing!!!

Reviewed on 23 November 2025

Appellation Healdsburg
Best Western Dry Creek Inn

Best Western Dry Creek Inn

3 out of 5
198 Dry Creek Rd Healdsburg CA
The price is SAR 448 per night from Dec 1 to Dec 2
SAR 448
SAR 521 total
1 Dec - 2 Dec
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Great stay. Clean, quiet room. However, bathroom faucet had significant leak that poured onto surface of sink and only produced hot water on both hot and cold settings.

Reviewed on 18 November 2025

Best Western Dry Creek Inn
See all 497 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 featuring flowers

Dry Creek Vineyard

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

Dry Creek Vineyard
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
Beautiful tasting room located in an old General Store dating to 1869.

Soda Rock Winery

You can enjoy a tasting or tour at Soda Rock Winery during your travels to Healdsburg. Amble around this romantic area's riverfront and enjoy its top-notch restaurants.

Soda Rock Winery

Frequently asked questions

How do I find cheap flights to Healdsburg that have flexible change policies?
At Expedia, we've been channeling our inner yoga master to offer you the most flexible airfares in town. Just tick the "No change fee" box directly beneath the "Flexible change policies" subheading to find the best flights to Healdsburg.
Which airlines fly to Healdsburg?
Pack your bags and choose between these popular airlines that service Healdsburg:

  • United Airlines - 5,167 flights to or near Healdsburg each month, including 5,167 flights to San Francisco Intl. Airport (SFO) per month.
  • Alaska Airlines - 2,483 flights to or near Healdsburg each month, including 2,197 flights to San Francisco Intl. Airport (SFO) per month.
  • American Airlines - 1,096 flights to or near Healdsburg each month, including 1,035 flights to San Francisco Intl. Airport (SFO) per month.

How can I find cheap tickets to Healdsburg?
Book well in advance, fly with budget airlines, use frequent flyer miles — there are loads of ways! One more is to make use of Expedia's "flexible dates" feature. Find a Healdsburg flight, then compare the prices for nearby dates. In the last seven days, the lowest price for a flight to Healdsburg was .
How much is a flight to Healdsburg?
The price of a round-trip airfare to Healdsburg in the last seven days ranged between and . If you were traveling one way from (), you could have gotten a cheap fare from only .
What are the most popular airports to fly into in Healdsburg?
Depending on your airline and city of departure, one of these well-known airports will be your entry point to Healdsburg:

  • San Francisco Intl. Airport (SFO) - 10,936 flights per month.
  • Sonoma County Airport (STS) - 433 flights per month.

When is the cheapest time to fly to Healdsburg?
Jet off earlier in the week to nab the best deal to Healdsburg. Tuesday is generally the cheapest day to depart, with Monday right behind it. Saturday typically has the highest prices. This is because lots of people choose to start their trip on a weekend.
How much is a plane ticket to Healdsburg?
In the last seven days, flights to Healdsburg fluctuated from to .
What months are the cheapest to book a flight to Healdsburg?
February is a good month to grab cheap flights to Healdsburg. Bear in mind that the costliest time to book in the States isn't the middle of summer, but the festive month of December.
How long is a flight to Healdsburg?
Your flight to Healdsburg could be long or short depending on where you set off from. Before you load your laptop with movies and audiobooks, have a look at the average flight times for these top domestic routes:

  • Los Angeles, CA (LAX-Los Angeles Intl.) to San Francisco Intl. Airport (SFO) - 1 hour and 33 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to San Francisco Intl. Airport (SFO) - 6 hours and 34 minutes
  • San Diego, CA (SAN-San Diego Intl.) to San Francisco Intl. Airport (SFO) - 1 hour and 43 minutes