Winter Gardens Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winter Gardens

Handlery Hotel

Handlery Hotel

3.5 out of 5
950 Hotel Cir N, San Diego, CA
Fully refundableReserve now, pay when you stay
8/10 Very Good! (2,002 reviews)
"Great pool and convenient location. I was surprised by the $24 a night fee to park a car in their parking lot, which is silly."

Reviewed on 26 Aug 2025

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Handlery Hotel
Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
1355 N Harbor Drive, San Diego, CA
Fully refundableReserve now, pay when you stay
The price is 4.002.458 ₫ per night from 1 Sept to 2 Sept
4.002.458 ₫
5.298.299 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (5,886 reviews)
Great view. Great location. Great shuttle.
"I had a really great time. The room could have been cleaner on arrival."

Reviewed on 24 Aug 2025

Wyndham San Diego Bayside
Bay Club Hotel & Marina

Bay Club Hotel & Marina

3.5 out of 5
2131 Shelter Island Dr, San Diego, CA
The price is 3.296.760 ₫ per night from 8 Sept to 9 Sept
3.296.760 ₫
3.789.461 ₫ total
8 Sept - 9 Sept
includes taxes & fees
9/10 Wonderful! (2,833 reviews)
Family trip 2025
"Best hotel we have stayed at by far! Lots to see and do near by. Food and drinks are amazing! It was such a vibe! Will definitely book again!"

Reviewed on 24 Aug 2025

Bay Club Hotel & Marina
See all 7,105 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

Lake Jennings

Commune with nature and explore the great outdoors at Lake Jennings during your travels in Lakeside. While in this romantic area, you can savour the top-notch restaurants.

Lake Jennings

Barona Creek Golf Club

Enjoy a round of golf in Lakeside at Barona Creek Golf Club. Make time to visit the area's casinos or simply enjoy its top-notch restaurants.

Barona Creek Golf Club

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.