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.
Embassy Hotel

Embassy Hotel

2.5 out of 5
Downtown San Francisco
Price was CA $628, price is now CA $362 per person
CA $362
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
7/10 Good! (245 reviews)
Seems like room was never cleaned

Reviewed on Aug. 20, 2025

The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Price was CA $1,632, price is now CA $883 per person
CA $883
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9/10 Wonderful! (652 reviews)
Super friendly and helpful staff. Great location. Nice and clean accommodations.

Reviewed on Aug. 21, 2025

Nob Hill Hotel

Nob Hill Hotel

4 out of 5
Downtown San Francisco
Price was CA $1,685, price is now CA $923 per person
CA $923
per person
Sep 23 - Sep 28
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
7.8/10 Good! (1,003 reviews)
Great place, except when you walk out the door.

Reviewed on Aug. 11, 2025

Treehouse Hotel Silicon Valley

Treehouse Hotel Silicon Valley

5 out of 5
Price was CA $3,536, price is now CA $1,941 per person
CA $1,941
per person
Sep 23 - Sep 30
found 12 hours ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9.8/10 Exceptional! (30 reviews)
Extremely detailed organized room. Excellent home like decor in the room. Awesome room condition, very big spacious and clean bathroom and soaking bath.

Reviewed on Aug. 8, 2025

Bay Landing San Francisco Airport Hotel

Bay Landing San Francisco Airport Hotel

3 out of 5
Price was CA $1,110, price is now CA $635 per person
CA $635
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9/10 Wonderful! (4,487 reviews)
Staff should start smiling and well coming !

Reviewed on Aug. 23, 2025

Ready to book your vacation to Healdsburg?

 

Choose your dates

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 CA $179 per night from Aug 24 to Aug 25
CA $179
CA $208 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,000 reviews)
good experience
"THE BEDS WERE COMFORTABLE The bathtub in our room 122 had some chips in it."

Reviewed on Aug. 18, 2025

Best Western Dry Creek Inn
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 CA $206 per night from Sep 1 to Sep 2
CA $206
CA $239 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (315 reviews)
"Location and amenities at the hotel"

Reviewed on Aug. 21, 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 CA $1,211 per night from Sep 22 to Sep 23
CA $1,211
CA $1,535 total
Sep 22 - Sep 23
includes taxes & fees
9.4/10 Exceptional! (104 reviews)
"Property itself is fantastic, especially the pool and rooms. However, the restaurant is….really not good. We’ve been to this property twice and we disappointed both times in the restaurant. Someone in our party ordered something for dinner that had a very bad, chemical-y taste. Such a shame, as a ..."

Reviewed on Aug. 17, 2025

Montage Healdsburg
See all 520 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Healdsburg

Dry Creek Vineyard which includes flowers

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
Mazzocco Winery

Mazzocco Winery

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

Mazzocco Winery

What to do in Healdsburg

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $69
per adult
84% 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
Ride

Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

CA $372
per adult
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
See all activities in Healdsburg

Frequently asked questions

How much does a Healdsburg vacation package cost?
You can grab a vacation package to this destination from CA $362 on Expedia. But how much your vacation to Healdsburg costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Healdsburg?
December, January and February are great times to search for cheap Healdsburg vacation packages. Choosing to travel in less busy periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Healdsburg?
The ideal length for your Healdsburg vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to go to all the top sights and discover some hidden treasures along the way.
Is it worth booking a vacation package to Healdsburg?
Healdsburg has everything you need for a wonderful escape. Get your Healdsburg vacation off to a flying start by visiting popular attractions like Healdsburg Plaza.
How to find the best Healdsburg package deals?
Landing a cheap Healdsburg package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Healdsburg package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Healdsburg vacation as a package?
You can enjoy significant savings on your Healdsburg retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Healdsburg?
Secure incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Healdsburg getaway.
How to plan a trip to Healdsburg?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to visit Healdsburg.
  2. Set a budget: Consider costs such as flights, transportation and food when working out how much to set aside for your trip to Healdsburg. Then, pick a hotel that suits your budget, whether that's an affordable stay or a more upscale getaway.
  3. Decide how long to go for: Now that you're up to speed on Healdsburg, you can figure out the ideal length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose 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.