Winter Gardens Vacations from $348

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was $629, price is now $348 per person
$348
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
8.8/10 Excellent! (2,743 reviews)

Hotel Z

Hotel Z

3 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,335, price is now $827 per person
$827
per person
Nov 30 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
9.2/10 Wonderful! (1,212 reviews)
The best part is having everything walking distance.

Reviewed on Oct 27, 2026

Los Bungalows

Los Bungalows

2.5 out of 5
Seacoast
Save 100% on your flight
Price was $615, price is now $391 per person
$391
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (567 reviews)

Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Mission Bay
Save 100% on your flight
Price was $1,147, price is now $749 per person
$749
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
8.8/10 Excellent! (2,946 reviews)

Pendry San Diego

Pendry San Diego

5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,339, price is now $878 per person
$878
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Diego (SAN)
9.4/10 Exceptional! (1,004 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Winter Gardens
View all trips

What to do in Winter Gardens

Wine tours perfect for bachelorettes

Chauffeured Adventure to Local San Diego Vineyards

$246
per adult
100% of travellers recommend
Chauffeured Adventure to Local San Diego Vineyards
San Diego: Guided Natural History Walk

San Diego: Guided Natural History Walk

$64
per adult
San Diego: Guided Natural History Walk
Wine Tour Private San Diego County

Wine Tour Private San Diego County

$699
per traveler
Wine Tour Private San Diego County
See all activities in Winter Gardens

Winter Gardens Hotel Deals

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
$182 nightly
The price is $211 total per night from Nov 1 to Nov 2
$211 total
Nov 1 - Nov 2
Total with taxes and fees
Wyndham San Diego Bayside
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
$203 nightly
The price is $235 total per night from Nov 22 to Nov 23
$235 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (4,567 reviews)
"The room was very clean and the cleaning staff was absolutely amazing. Cleanest room I've ever seen."

Reviewed on Oct 27, 2026

Hard Rock Hotel San Diego
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
$269 nightly
The price is $309 total per night from Nov 15 to Nov 16
$309 total
Nov 15 - Nov 16
Total with taxes and fees
Paradise Point Resort & Spa
See all 7,618 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winter Gardens vacation package cost?
Offering excellent value package deals from $348 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.