Winter Gardens Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Top hotels in Winter Gardens

Handlery Hotel

Handlery Hotel

3.5 out of 5
950 Hotel Cir N, San Diego, CA
The price is S$164 per night from 21 Jul to 22 Jul
S$164
21 Jul - 22 Jul
includes taxes & fees
8/10 Very Good! (1,868 reviews)
Nice place great value
"Great spot for the price point. A bit dayed but clean. Nice pool and pool bar and grounds are nice. A great value"

Reviewed on 14 Jul, 2025

Handlery Hotel
Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
1355 N Harbor Drive, San Diego, CA
The price is S$238 per night from 22 Jul to 23 Jul
S$238
22 Jul - 23 Jul
includes taxes & fees
8.2/10 Very Good! (5,720 reviews)
"Great staff! The only thing was that our deadbolt didn’t work. Otherwise, it was great!"

Reviewed on 13 Jul, 2025

Wyndham San Diego Bayside
Marriott Marquis San Diego Marina

Marriott Marquis San Diego Marina

4 out of 5
333 W Harbor Dr, San Diego, CA
The price is S$405 per night from 20 Jul to 21 Jul
S$405
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (1,741 reviews)
"Great location, served its purpose for the 4Th"

Reviewed on 11 Jul, 2025

Marriott Marquis San Diego Marina
See all 7,067 properties in Winter Gardens
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.

Popular places to visit

Barona Casino

Why not try your luck with a visit to Barona Casino during your travels in Lakeside? Discover the area's casinos or seek out its golf courses.

Barona Casino

What to do in Winter Gardens

Find local wildlife with an expert guide with a deep knowledge of San Diego's nature.

Small Group Hike Through San Diego's Heart and Soul

S$82
per adult
Small Group Hike Through San Diego's Heart and Soul
Cruise & Booze Brewery tours

Cruise & Booze Brewery tours

S$191
per adult
100% of travellers recommend
Cruise & Booze Brewery tours
Chauffeured Adventure to Local San Diego Vineyards

Chauffeured Adventure to Local San Diego Vineyards

S$315
per adult
100% of travellers recommend
Chauffeured Adventure to Local San Diego Vineyards
See all activities in Winter Gardens

Frequently asked questions

How much does a Winter Gardens holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Winter Gardens costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winter Gardens?
The off-season is the best time to head to Winter Gardens if you're trying to save. Another tip for scoring cheap Winter Gardens holiday packages? Try to avoid public holidays and any major festivals.
How many days is enough for Winter Gardens?
The ideal duration of your Winter Gardens holiday depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to visit all the top attractions and discover some hidden treasures along the way.
How to find the best Winter Gardens package deals?
Use Expedia's filters to help you find some terrific Winter Gardens package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winter Gardens package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Winter Gardens holiday as a package?
You can enjoy significant savings on your Winter Gardens getaway by booking a tailored holiday package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Winter Gardens?
Score amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Winter Gardens break.
How to plan a trip to Winter Gardens?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred season and the type of activities available will also help you decide when to visit Winter Gardens.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to save for your trip to Winter Gardens. Then, select a hotel that matches your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide how long to go away for: Now that you're more familiar with Winter Gardens, you can work out the ideal length of your break. Create a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Winter Gardens 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.