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Healdsburg Vacations

Pack those stellar shades. We have Healdsburg vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Healdsburg – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Healdsburg vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Healdsburg

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Healdsburg vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Healdsburg well.

Healdsburg Flight + Hotel packages

Top Hotel Deals

See all 472 Hotels in Healdsburg
Best Western Dry Creek Inn

Best Western Dry Creek Inn

198 Dry Creek Rd, Healdsburg
3.5 out of 5.0

This Healdsburg hotel is within 10 miles of over 200 wineries, the River Rock Casino, and Lake Sonoma.

$119

$119
Hotel Healdsburg

Hotel Healdsburg

25 Matheson St, Healdsburg
4.5 out of 5.0

Located in the heart of Healdsburg, this spa hotel is within a 5-minute walk of Healdsburg Plaza, Healdsburg Center for the Arts, and Raven Performing Arts Theater. ...

$349

$349
Americas Best Value Inn and Suites - Healdsburg

Americas Best Value Inn and Suites - Healdsburg

74 Healdsburg Ave, Healdsburg
2.5 out of 5.0

Situated in Healdsburg, this motel is within a 15-minute walk of Healdsburg Plaza, Pezzi King Winery, and Healdsburg Center for the Arts. Raven Performing Arts ...

$79

$79
h2hotel

h2hotel

219 Healdsburg Ave, Healdsburg
4.0 out of 5.0

Located in the heart of Healdsburg, this hotel is within a 5-minute walk of Healdsburg Plaza, Healdsburg Center for the Arts, and Raven Performing Arts Theater. ...

$249

$249
Hotel Les Mars

Hotel Les Mars

27 North St, Healdsburg
4.5 out of 5.0

Located in the heart of Healdsburg, this romantic hotel is steps from Raven Performing Arts Theater and Healdsburg Plaza. Healdsburg Center for the Arts and ...

$332

$332
Calderwood Inn

Calderwood Inn

25 West Grant Street, Healdsburg
4.0 out of 5.0

Situated in Healdsburg, this romantic guesthouse is within a 15-minute walk of Raven Performing Arts Theater, Healdsburg Plaza, and Healdsburg Center for the ...

Travelodge Healdsburg - Sonoma Wine Country

Travelodge Healdsburg - Sonoma Wine Country

178 Dry Creek Rd, Healdsburg
2.5 out of 5.0

Situated in Healdsburg, this motel is within 1 mi (2 km) of Simi Winery and Raven Performing Arts Theater. Healdsburg Plaza and Healdsburg Center for the Arts ...

$101

$101
Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg Inn on the Plaza, A Four Sisters Inn

112 Matheson, Healdsburg
4.0 out of 5.0

Located in the heart of Healdsburg, this romantic bed & breakfast is steps from Healdsburg Plaza, Healdsburg Center for the Arts, and Raven Performing Arts Theater. ...

Grape Leaf Inn

Grape Leaf Inn

539 Johnson Street, Healdsburg
4.5 out of 5.0

Situated in Healdsburg, this romantic bed & breakfast is within a 10-minute walk of Raven Performing Arts Theater, Healdsburg Center for the Arts, and Healdsburg ...

Camellia Inn

Camellia Inn

211 North Street, Healdsburg
4.0 out of 5.0

Situated in a national park, this bed & breakfast is close to Healdsburg Center for the Arts, Raven Performing Arts Theater, and Healdsburg Museum. Also nearby ...

$251

$251

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.