Healdsburg Vacations from $347

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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.

The Latest Healdsburg vacation packages

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
Save 100% on your flight
Price was $581, price is now $347 per person
$347
per person
Oct 30 - Nov 2
found 2 days ago
Roundtrip flight included
Dallas (DFW) to San Francisco (SFO)
9/10 Wonderful! (6,641 reviews)
The location and good service adds to the charm of the hotel.

Reviewed on Aug 20, 2025

The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Save 100% on your flight
Price was $1,057, price is now $588 per person
$588
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Francisco (SFO)
9/10 Wonderful! (652 reviews)
Very nice property in a great location. Short walk to the painted laidies, restaurants and shops on Divisedero. Bus stop right there to take directly to the Fillmore, Castro, lower Haight, or the Mission.

Reviewed on Aug 7, 2025

Bay Landing San Francisco Airport Hotel

Bay Landing San Francisco Airport Hotel

3 out of 5
Save 100% on your flight
Price was $829, price is now $487 per person
$487
per person
Sep 26 - Sep 30
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to San Francisco (SFO)
9/10 Wonderful! (4,470 reviews)
CLEAN, Check-in was a Breeze, Staff was excellent!!!! AND only 5minutes to SFO Airport ! Will stay here on our next visit ! Bay Landing exceeded our expectations.

Reviewed on Aug 20, 2025

Embassy Hotel

Embassy Hotel

2.5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $684, price is now $418 per person
$418
per person
Sep 26 - Sep 30
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to San Francisco (SFO)
6.8/10 (199 reviews)
Seems like room was never cleaned

Reviewed on Aug 20, 2025

Vinarosa Resort & Spa

Vinarosa Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,862, price is now $1,180 per person
$1,180
per person
Oct 6 - Oct 13
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to San Francisco (SFO)
9.2/10 Wonderful! (754 reviews)
The property was recently renovated and looks amazing. The room we stayed in was beautifully upgraded and very spacious. The room had a fireplace and the balcony overlooked the vineyards. The resort grounds around the property are lovely. There is a walking path that led into the vineyards. The property also has multiple seating areas with firepits for guests to enjoy. The pool is perfect for relaxing after a day of wine tasting. Wish though that the pool side bar would stay open a little later. We had a great stay overall and we hope to be back here for another visit.

Reviewed on Aug 2, 2025

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Discover the most popular places to visit in Healdsburg

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

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

Healdsburg Plaza

Find out about the history of Healdsburg with a stop at Healdsburg Plaza. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Healdsburg Plaza

What to do in Healdsburg

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

$50
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

$139
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

$270
per adult
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
See all activities in Healdsburg

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
$129 nightly
The price is $150 total per night from Aug 24 to Aug 25
$150 total
Aug 24 - Aug 25
Total includes taxes and 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
$149 nightly
The price is $173 total per night from Sep 1 to Sep 2
$173 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (312 reviews)
"Was nice for the price for sure!"

Reviewed on Aug 17, 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
$913 nightly
The price is $1,077 total per night from Sep 10 to Sep 11
$1,077 total
Sep 10 - Sep 11
Total includes taxes and 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 516 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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Frequently asked questions

How much does a Healdsburg vacation package cost?
You can grab a vacation package to this popular destination from $347 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?
September, October and December are great times to search for cheap Healdsburg vacation packages. Traveling in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Healdsburg?
With a well-planned schedule, you can easily tick off the top Healdsburg attractions in a handful of days. But if you'd like to venture off the beaten track or go on day trips, consider booking your Healdsburg vacation for longer.
Is it worth booking a vacation package to Healdsburg?
It's easy to see why a Healdsburg vacation is on the to-do list of many travelers. Well-known attractions like Healdsburg Plaza are just the start 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 your dates: What you want to do in Healdsburg and your preferred season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to pay for everything from food and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Healdsburg.
  3. Explore Healdsburg with Expedia's trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Healdsburg. You can also save your must-visit places, collaborate with your group and arrange all your plans in one place.
  4. Work out your trip length: Consider how long you want to spend discovering Healdsburg. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the ideal Healdsburg vacation package for you.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some exciting things to do in Healdsburg. Book tickets or make reservations before you go to save time and skip the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Healdsburg vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Healdsburg vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.