Healdsburg Vacations from ￥142,128

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Healdsburg Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Zeppelin San Francisco

Hotel Zeppelin San Francisco

4 out of 5
Union Square
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tokyo (NRT) to San Francisco (SFO)
8.6/10 Excellent! (1,003 reviews)
The design was cool, and I really enjoyed the on site restaurant.

Reviewed on Aug 11, 2025

DoubleTree by Hilton San Francisco Airport North Bayfront

DoubleTree by Hilton San Francisco Airport North Bayfront

4 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to San Francisco (SFO)
8/10 Very Good! (1,205 reviews)
Place was great and easy tonget to

Reviewed on Aug 9, 2025

@ Marbella Lane - Modern Refreshing Home

@ Marbella Lane - Modern Refreshing Home

3 out of 5
Central San Mateo
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to San Francisco (SFO)
No reviews
Hilton Garden Inn San Francisco Arpt North

Hilton Garden Inn San Francisco Arpt North

3 out of 5
The East Side
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to San Francisco (SFO)
8.6/10 Excellent! (1,006 reviews)
People are nice working there

Reviewed on Aug 12, 2025

Hotel 1550

Hotel 1550

3.5 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to San Francisco (SFO)
9/10 Wonderful! (1,003 reviews)
It seems like a smaller boutique hotel like this is able to give you better service, at least that was my experience. I would not hesitate to book this hotel again.

Reviewed on Aug 14, 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 ￥21,940 per night from Sep 2 to Sep 3
￥21,940
￥25,494 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (311 reviews)
"Property is really nice and in a great location! Service/staff was wonderful. So friendly and nice and kind. Our room was lovely except for the fact that the carpet was very dirty and the floor wasn’t clean at all. Our feet were black from walking around the room and we had to wash them constantly. ..."

Reviewed on Aug 14, 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 ￥125,163 per night from Sep 10 to Sep 11
￥125,163
￥158,625 total
Sep 10 - Sep 11
includes taxes & fees
9.4/10 Exceptional! (103 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 ￥19,067 per night from Sep 2 to Sep 3
￥19,067
￥22,155 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Trip to Windsor with the girls ❤️
"We ate at Peppers food was great & close to the Hotel which was nice, our beds were comfy & internet worked great wish there would have been a hot tub & breakfast in the morning but other then that it was nice"

Reviewed on Aug 12, 2025

Best Western Dry Creek Inn
See all 512 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
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

￥20,529
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
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 ￥142,128 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.