Winter Gardens Vacations from $351

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Your Winter Gardens Vacation

Reserve a Winter Gardens vacation package and get set to experience the best of this lively city. Consider staying in the neighborhood of Central San Diego, which is good for views, culture and dining. Any trip to Winter Gardens has to include a little sightseeing. Lake Jennings is a superb place to start your exploring. No matter your travel plans or budget, organizing your ultimate tailored Winter Gardens vacation is a walk in the park with Expedia.

The Latest Winter Gardens vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyland Inn Near Legoland

Hyland Inn Near Legoland

3 out of 5
Olde Carlsbad
Save 100% on your flight
Price was $616, price is now $351 per person
$351
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
7.8/10 Good! (1,007 reviews)
I was expecting this hotel to be a good spot for my family and I to rest. The covers had stains on it . The room still had trash, ĺ

Reviewed on Apr 7, 2026

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,353, price is now $762 per person
$762
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
8.6/10 Excellent! (1,868 reviews)
I really enjoyed my stay here. The staff was very helpful and friendly. The interior is all upgraded and nice. I would definitely stay here again

Reviewed on Apr 9, 2026

Hyatt Vacation Club at The Welk, San Diego Area

Hyatt Vacation Club at The Welk, San Diego Area

3.5 out of 5
Lawrence Welk Resort Village
Save 100% on your flight
Price was $1,405, price is now $844 per person
$844
per person
May 22 - May 28
found 1 hour ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
8.4/10 Very Good! (1,686 reviews)
The staff was great, I had a problem with the food and the grille. My food tasted weird, they did great and gave my son something different. The biggest issue I had was with the text message service. It was difficult to get what I needed from this number as they did not respond. I attempted multiple times and it was still no success. Overall the stay was good and hopefully they can resolve this issue.

Reviewed on Apr 9, 2026

Little Italy Inn - Limited Service Apart Hotel

Little Italy Inn - Limited Service Apart Hotel

2.5 out of 5
Downtown San Diego
Price was $834, price is now $514 per person
$514
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
8.4/10 Very Good! (117 reviews)
Room was amazing and cozy

Reviewed on Dec 1, 2025

Ocean Park Inn

Ocean Park Inn

3 out of 5
Pacific Beach
Save 100% on your flight
Price was $2,023, price is now $1,281 per person
$1,281
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
9.4/10 Exceptional! (1,015 reviews)
Great location, didn’t need a car for our 4 day stay, right on the beach. Friendly staff

Reviewed on Apr 10, 2026

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Discover the most popular places to visit in Winter Gardens

Barona Creek Golf Club

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
People fish from boats at Lake Jennings in Lakeside, California located in San Diego County also a popular destination for hiking, camping and picnicking.

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 savor the top-notch restaurants.

Lake Jennings

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

Wine tours perfect for bachelorettes

Chauffeured Adventure to Local San Diego Vineyards

$221
per adult
100% of travellers recommend
Chauffeured Adventure to Local San Diego Vineyards
See all activities in Winter Gardens

Winter Gardens Hotel Deals

Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
1404 Vacation Rd San Diego CA
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $259 total per night from May 10 to May 11
$259 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (2,540 reviews)
This resort was family friendly. The staff were always prompt to meet our needs.

Reviewed on Apr 11, 2026

Paradise Point Resort & Spa
Best Western Seven Seas

Best Western Seven Seas

3 out of 5
411 Hotel Circle South San Diego CA
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $94 total per night from Apr 21 to Apr 22
$94 total
Apr 21 - Apr 22
Total with taxes and fees
7.8/10 Good! (3,380 reviews)
Yes

Reviewed on Apr 11, 2026

Best Western Seven Seas
Hard Rock Hotel San Diego

Hard Rock Hotel San Diego

4 out of 5
207 5th Ave San Diego CA
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $308 total per night from Apr 15 to Apr 16
$308 total
Apr 15 - Apr 16
Total with taxes and fees
9/10 Wonderful! (3,531 reviews)
Location is great for Petco Park or Gaslamp district.

Reviewed on Apr 11, 2026

Hard Rock Hotel San Diego
See all 7,393 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.

Find the Best Winter Gardens Vacation Packages

Winter Gardens Essential Information

Language
English
Currency
U.S dollars
Closest Airport
San Diego Intl. Airport (SAN)
Population
20,600
Top Sights
Barona Casino, Lake Jennings and Barona Creek Golf Club

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Frequently asked questions

How much does a Winter Gardens vacation package cost?
Offering excellent value package deals from $351 on Expedia, you'll be pleasantly surprised at how much a vacation 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?
If you're hoping to score a cheap Winter Gardens vacation package, consider visiting in January, October and December. You'll usually find better rates on flights and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for Winter Gardens?
The ideal length of your Winter Gardens vacation depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to go to all the main sights and explore 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 vacation package as early as possible.
Is it cheaper to book a Winter Gardens vacation as a package?
You can enjoy significant savings on your Winter Gardens getaway by booking a tailored vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Winter Gardens vacation packages?
Set off on your perfect trip to Winter Gardens with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.