Healdsburg Vacation Packages

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Your Healdsburg Vacation

When a getaway to the city is calling, answer it with a Healdsburg vacation package. The neighborhood of Forest Hills, which is great for nature, hiking and views, makes a terrific base for your adventures. If your trip to Healdsburg includes some sightseeing, hit up major attractions such as Healdsburg Plaza, Russian River and Francis Ford Coppola Winery. Whoever you're escaping with and whatever your budget, your ultimate Healdsburg vacation is just a few clicks away with Expedia.

Top Healdsburg Vacation Deals

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

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Price was CA $1,756, price is now CA $1,233 per person
CA $1,233
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9/10 Wonderful! (7,441 reviews)
Always an excellent stay, great breakfast, nice rooms.

Reviewed on May 12, 2026

@ Marbella Lane - Natural Bayview Escape Near SFO

@ Marbella Lane - Natural Bayview Escape Near SFO

3 out of 5
Colma
Price was CA $5,007, price is now CA $3,347 per person
CA $3,347
per person
Aug 7 - Aug 10
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Francisco (SFO)
No reviews
Treehouse Hotel Silicon Valley

Treehouse Hotel Silicon Valley

5 out of 5
Price was CA $2,214, price is now CA $1,516 per person
CA $1,516
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Francisco (SFO)
9.8/10 Exceptional! (90 reviews)
We had a great time celebrating my husband's birthday there. We thought we had to venture out to grab meals around the area, but the food there were great. And we just have a relaxing time there.

Reviewed on Apr 5, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was CA $2,614, price is now CA $1,849 per person
CA $1,849
per person
Jul 5 - Jul 8
found 9 hours ago
Roundtrip flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (540 reviews)
Amazing ambiance. Great staff and Daily Breakfast.

Reviewed on Apr 10, 2026

Fairmont Heritage Place, Ghirardelli Square

Fairmont Heritage Place, Ghirardelli Square

5 out of 5
Fisherman's Wharf
Price was CA $4,966, price is now CA $3,575 per person
CA $3,575
per person
Aug 5 - Aug 9
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
9.4/10 Exceptional! (400 reviews)
This is my favorite San Francisco hotel/condo. I’ve stayed here five times and highly recommend it.

Reviewed on May 6, 2026

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Healdsburg Hotel Deals

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

3 out of 5
198 Dry Creek Road Healdsburg CA
The price is CA $177 per night from May 17 to May 18
CA $177
CA $206 total
May 17 - May 18
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Great property. Great value. Peppers is amazing.

Reviewed on May 10, 2026

Dry Creek Inn MOD Collection by Sonesta
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
The price is CA $208 per night from May 26 to May 27
CA $208
CA $242 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (472 reviews)
Great location. Very comfortable room.

Reviewed on May 11, 2026

The Lodge at Healdsburg, Tapestry Collection by Hilton
Hotel Trio Healdsburg

Hotel Trio Healdsburg

3 out of 5
110 Dry Creek Rd Healdsburg CA
The price is CA $243 per night from May 20 to May 21
CA $243
CA $311 total
May 20 - May 21
includes taxes & fees
9.4/10 Exceptional! (925 reviews)
This property is a good location, however, if you’re looking to walk into town our have the feeling of “in town” you’ll be disappointed. The walkable path is a good 20 minutes. There is also no daily housekeeping. If I had know both of these things I would have chosen a different location.

Reviewed on May 11, 2026

Hotel Trio Healdsburg
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.
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Discover the most popular places to visit in Healdsburg

Dry Creek Vineyard

Dry Creek Vineyard

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

Dry Creek Vineyard
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

Mazzocco Winery

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

What to do in Healdsburg

Shopping in Healdsburg

History Walking Tour of Healdsburg

CA $62
per adult
History Walking Tour of Healdsburg
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $69
per adult
86% 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

CA $191
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Healdsburg

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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.