Healdsburg Vacations from ￥238,899

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The Latest Healdsburg Vacation Packages

Hotel Stratford

Hotel Stratford

2 out of 5
Downtown San Francisco
per person
Jul 5 - Jul 12
Roundtrip non-stop flight included
Tokyo (HND) to San Francisco (SFO)
8.2/10 Very Good! (458 reviews)
Amazing experience Cute hotel

Reviewed on Apr 17, 2024

Larkspur Landing Sunnyvale - An All-Suite Hotel

Larkspur Landing Sunnyvale - An All-Suite Hotel

3 out of 5
per person
May 26 - May 31
Roundtrip non-stop flight included
Tokyo (TYO) to San Francisco (SFO)
8.4/10 Very Good! (1,000 reviews)
It was cold as they have this nonsense AC heaters with motion detectors so everything stops at night

Reviewed on Jan 25, 2024

Cherry Orchard Inn

Cherry Orchard Inn

2.5 out of 5
Ponderosa Park
per person
May 26 - May 31
Roundtrip non-stop flight included
Tokyo (TYO) to San Francisco (SFO)
7.2/10 Good! (995 reviews)
average outside but inside very cute and updated so we decided to extend our stay

Reviewed on Jan 16, 2024

The Westin St. Francis San Francisco on Union Square

The Westin St. Francis San Francisco on Union Square

4.5 out of 5
Downtown San Francisco
per person
Jul 5 - Jul 12
Roundtrip non-stop flight included
Tokyo (HND) to San Francisco (SFO)
8.8/10 Excellent! (2,665 reviews)
Beautiful hotel! Great amenities and walkable to the areas I needed.

Reviewed on Apr 17, 2024

SF Central Hotel

SF Central Hotel

2 out of 5
South of Market
per person
Jun 9 - Jun 14
Roundtrip non-stop flight included
Tokyo (HND) to San Francisco (SFO)
6.2/10 (481 reviews)
reasonable for the price, but the bathroom window was about to fall out of its frame & it was pretty loud even when the door & the blinds were all closed. nighttime staff was not friendly, but morning staff were fine at check out.

Reviewed on Apr 14, 2024

Prices and availability subject to change. Additional terms may apply.

Healdsburg Hotel Deals

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 ￥22,446 per night from Apr 22 to Apr 23
￥22,446
per night
Apr 22 - Apr 23
7.8/10 Good! (1,000 reviews)
Pleasant stay.
"Very pleasant front desk staff. Easy check in/out. 15 min walk down paved trail to central Healdsburg. Across the street is a great coffee shop. Rooms are a little noisy if you’re a light sleeper. I could understand conversation in next room. Clean and somewhat updated for an old building."

Reviewed on Apr 10, 2024

Best Western Dry Creek Inn
Hotel Trio Healdsburg
Hotel Trio Healdsburg
3 out of 5
110 Dry Creek Rd, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is ￥31,862 per night from Apr 21 to Apr 22
￥31,862
per night
Apr 21 - Apr 22
9.2/10 Wonderful! (633 reviews)
"Our units AC didn’t work but they offered to put us in another room."

Reviewed on Apr 13, 2024

Hotel Trio Healdsburg
Harmon Guest House
Harmon Guest House
3 out of 5
227 Healdsburg Avenue, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is ￥52,301 per night from Apr 28 to Apr 29
￥52,301
per night
Apr 28 - Apr 29
9.4/10 Exceptional! (309 reviews)
"Great property and location. Would definitely stay here again."

Reviewed on Apr 14, 2024

Harmon Guest House
See all 549 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 vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Healdsburg from just ￥238,899. And the more you bundle, the more money you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Healdsburg?
Bundle your bookings with Expedia to save big bucks on your next big adventure. With more than 550 partner airlines and 1,000,000 hotel options globally, your Healdsburg vacation package can be tailored exactly to suit your travel style. With all those extra dollars, why not throw in one or more fun experiences and tours? It’s an easy way to unlock even more discounts. That dream vacation to Healdsburg is much closer than you thought!
Where should I stay in Healdsburg?
Stay where the action happens. Many visitors favor hotels in the vicinity of popular sights, such as Healdsburg Plaza, Dry Creek Vineyard and Mazzocco Winery.
What are the top hotels in Healdsburg?
Xanadu Healdsburg - Luxury Blu Home In The Heart Of Sonoma County Wine Country and Montage Healdsburg are two of the most well-known properties in Healdsburg. Why not take a look at the amenities and facilities at each and then decide?
How far in advance should I book my Healdsburg vacation?
To land cheap prices, book nice and early. Air carriers generally advertise flight tickets, along with some of the lowest fares, around a year ahead of time. Hotels, activities and car rental should also be booked early to avoid disappointment. If you’re in need of a last-minute getaway to Healdsburg, there are always lots of great deals to be had on Expedia. Check them out now!
What does an Expedia Healdsburg travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your ideal Healdsburg package. Once you’ve made your booking, you can add on fun stuff like activities and tours. Remember, the more you bundle, the more you stand to save!
What should I know before booking a Healdsburg travel package?
Bundling your bookings into a Healdsburg vacation package is the easiest way to organize your trip. Not only that, you’ll get great discounts when you combine your hotels, flights and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Healdsburg Expedia vacation package?
With a vacation package, you’re in charge. Whether you’d like to fly to Healdsburg in business or coach, simply select from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Healdsburg vacation package?
You can cancel your Healdsburg booking if your travel plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Healdsburg

Image for Dry Creek Vineyard

Dry Creek Vineyard

5/5(10 reviews)

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

Dry Creek Vineyard
Image for Mazzocco Winery

Mazzocco Winery

3.5/5(2 reviews)

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

Mazzocco Winery
Image for Soda Rock Winery

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

What to do in Healdsburg

Image for Sonoma County: Tasting Pass (Choose 1, 2, or 90 Days)

Sonoma County: Tasting Pass (Choose 1, 2, or 90 Days)

￥5,745
Per adult
Sonoma County: Tasting Pass (Choose 1, 2, or 90 Days)
Image for Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

￥39,774
Per adult
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
Image for History Walking Tour of Healdsburg

History Walking Tour of Healdsburg

￥6,629
Per adult
History Walking Tour of Healdsburg
See all activities in Healdsburg

Other vacations you might like

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