Healdsburg Vacations from ￥181,186

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The Latest Healdsburg Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Zoe Fisherman's Wharf

Hotel Zoe Fisherman's Wharf

4 out of 5
Fisherman's Wharf
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to San Francisco (SFO)
9.2/10 Wonderful! (1,398 reviews)
Really pretty spartan for $500/night. Was fine and I understand it is in "good location", but was a pretty basic room for $500/night.

Reviewed on Aug 5, 2025

Hotel Zeppelin San Francisco

Hotel Zeppelin San Francisco

4 out of 5
Union Square
Save 100% on your flight
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to San Francisco (SFO)
8.6/10 Excellent! (1,008 reviews)
There were zero VIP options given, wine, upgrade etc. The staff member who checked us in seemed a bit out of sorts. That said the hotel is excellent in decor, location and walkability. Great breakfast nearby at Pinecrest Diner. PLS downstairs had great drinks and happy hour specials.

Reviewed on Aug 2, 2025

Hotel Zelos San Francisco

Hotel Zelos San Francisco

4 out of 5
Downtown San Francisco
Save 100% on your flight
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to San Francisco (SFO)
9/10 Wonderful! (1,003 reviews)
Great location and the hotel has a great vibe. I’d stay here again but note there is a fee of $35 per day after you check out that Expedia didn’t capture.

Reviewed on Jul 17, 2025

The Donatello

The Donatello

3.5 out of 5
Union Square
Save 100% on your flight
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to San Francisco (SFO)
9.2/10 Wonderful! (1,000 reviews)
Great hotel, club lounge and locker rooms are great.

Reviewed on Aug 4, 2025

Inn At The Opera

Inn At The Opera

3.5 out of 5
Fillmore District
Save 100% on your flight
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to San Francisco (SFO)
8.4/10 Very Good! (693 reviews)
Enjoyed the atmosphere of this inn. Very cute and decorated nicely. Love the ballet theme on our room.

Reviewed on Jul 13, 2025

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 ￥21,891 per night from Sep 1 to Sep 2
￥21,891
￥25,436 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (306 reviews)
We love Healdsburg
"The bed was very comfortable, the shower was huge, in a good way, and the wine was delicious"

Reviewed on Aug 1, 2025

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 ￥124,882 per night from Aug 27 to Aug 28
￥124,882
￥158,267 total
Aug 27 - Aug 28
includes taxes & fees
9.4/10 Exceptional! (101 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 Jun 1, 2025

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 ￥19,025 per night from Sep 1 to Sep 2
￥19,025
￥22,106 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"It was close to everything and it was incredibly safe"

Reviewed on Aug 4, 2025

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.

What to do in Healdsburg

Winter Ride

Sonoma Horseback-Riding Tour

￥19,052
per adult
100% of travellers recommend
Sonoma Horseback-Riding Tour
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

￥7,385
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Self Guided Audio Driving Tour from Vancouver to Whistler

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

￥2,509
per traveler
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
See all activities in Healdsburg

Frequently asked questions

How much does a Healdsburg vacation package cost?
You can grab a vacation package to this popular destination from ￥181,186 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.