
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
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
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
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


Inn At The Opera
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
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

Montage Healdsburg
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

Best Western Dry Creek Inn
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
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

Sonoma Horseback-Riding Tour
¥19,052
per adult
100% of travellers recommend

Icon Wine & Food Pairing at Williamson Wines in Healdsburg
¥7,385
per adult
84% of travellers recommend

Self-Guided Audio Driving Tour of Sonoma and Napa Valley
¥2,509
per traveler
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.