Healdsburg Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Find the Best Healdsburg Vacation Packages

Healdsburg Hotel Deals

Appellation Healdsburg

Appellation Healdsburg

4.5 out of 5
101 Dovetail Ln, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is ₩431,650 per night from Nov 30 to Dec 1
₩431,650
₩601,289 total
Nov 30 - Dec 1
includes taxes & fees
9.6/10 Exceptional! (12 reviews)
Room itself is very clean and nicely designed. Staffs are friendly and helpful. One thing to call out- we were charged a resort fee of $70/day. This charge was not shown and communicated when we were booking the room on the Expedia site nor were we told upon check-in. We only found out when we were ...

Reviewed on Oct 20, 2025

Appellation Healdsburg
Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is ₩975,421 per night from Dec 1 to Dec 2
₩975,421
₩1,236,930 total
Dec 1 - Dec 2
includes taxes & fees
9.4/10 Exceptional! (111 reviews)
Absolutely stunning!!!

Reviewed on Oct 5, 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 ₩185,234 per night from Nov 12 to Nov 13
₩185,234
₩215,231 total
Nov 12 - Nov 13
includes taxes & fees
7.8/10 Good! (1,003 reviews)
Beautiful place to stay. Was very surprised. Room was nice. Bed was comfortable. If there was a negative, water pressure wasn’t the best. Totally adequate though. Furniture was cute and loved the TV.

Reviewed on Oct 29, 2025

Best Western Dry Creek Inn
See all 489 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.

Discover the most popular places to visit in Healdsburg

Dry Creek Vineyard featuring flowers

Dry Creek Vineyard

5/5(10 reviews)

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

Dry Creek Vineyard
It’s barrel tasting weekend here along the wine road.

Mazzocco Winery

3.5/5(2 reviews)

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.