Healdsburg Holidays

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Healdsburg Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Stanford Court San Francisco

Stanford Court San Francisco

4 out of 5
Downtown San Francisco
Price was S$3,095, price is now S$1,975 per person
S$1,975
per person
17 Dec - 23 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9/10 Wonderful! (1,793 reviews)

The Huntington Hotel

The Huntington Hotel

5 out of 5
Downtown San Francisco
Price was S$5,227, price is now S$3,323 per person
S$3,323
per person
17 Dec - 23 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9.6/10 Exceptional! (44 reviews)

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was S$3,908, price is now S$2,880 per person
S$2,880
per person
17 Dec - 23 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9.2/10 Wonderful! (633 reviews)
Convenient car service and incredibly helpful staff and concierge. Rooms appeared modern with nice amenities and well maintained. Great stay.

Reviewed on 9 Nov, 2026

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Price was S$2,698, price is now S$2,117 per person
S$2,117
per person
17 Dec - 23 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9/10 Wonderful! (7,739 reviews)
Hotel Riu Plaza Fisherman’s Wharf is friendly and comfortable for vacation tourists. It is very convenient with public transit such as Muni F, 8 and 22, etc. Especially, it provides very good breakfast!

Reviewed on 14 Nov, 2026

Marines Memorial Club & Hotel

Marines Memorial Club & Hotel

4 out of 5
Union Square
Price was S$2,618, price is now S$2,125 per person
S$2,125
per person
17 Dec - 23 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9.6/10 Exceptional! (236 reviews)
Very well located, close to Union square and T/bart, restaurants, car rental or bike rental..Very nice staff, complementary breakfast and happy hours made our stay smooth and comfortable. It was a quiet week, and so a quiet room at night. Will come back.

Reviewed on 13 Nov, 2026

Top hotels in Healdsburg

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

3 out of 5
198 Dry Creek Road Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is S$178 per night from 15 Nov to 16 Nov
S$178
15 Nov - 16 Nov
includes taxes & fees
Dry Creek Inn MOD Collection by Sonesta
Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is S$1,249 per night from 6 Dec to 7 Dec
S$1,249
6 Dec - 7 Dec
includes taxes & fees
9.6/10 Exceptional! (143 reviews)
"Amazing!"

Reviewed on 4 Nov, 2026

Montage Healdsburg
Appellation Healdsburg

Appellation Healdsburg

4.5 out of 5
101 Dovetail Ln Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is S$487 per night from 23 Nov to 24 Nov
S$487
23 Nov - 24 Nov
includes taxes & fees
Appellation Healdsburg
See all 521 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.

Stay near popular Healdsburg attractions

Dry Creek Vineyard

9.4/10 (126 reviews)
Historic Dry Creek Vineyard pioneered Sauvignon Blanc planting in the region after Prohibition. Enjoy private seated tastings amid Loire Valley-inspired grounds perfect for an afternoon picnic.
See properties

What to do in Healdsburg

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

S$22
per traveller
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
Shopping in Healdsburg

History Walking Tour of Healdsburg

S$57
per adult
History Walking Tour of Healdsburg
Napa Valley Self-Guided Wine Tour: GPS Audio Driving Guide

Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide

S$51
per traveller
Napa Valley Wine Tour: Self-Guided GPS Audio Driving Guide
See all activities in Healdsburg

Frequently asked questions

How much does a Healdsburg holiday package cost?
You can grab a holiday package to this popular destination from S$1,975 on Expedia. But how much your holiday 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 holiday packages. Travelling 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-organised 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 holiday for longer.
Is it worth booking a holiday package to Healdsburg?
It's no wonder a Healdsburg holiday is on the to-do list of many travellers. 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 holiday as a package?
You can enjoy significant savings on your next Healdsburg getaway by booking a personalised holiday 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 holiday 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 accommodation 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.