Winter Gardens Vacation Packages

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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.

Top Winter Gardens Vacation Deals

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 CA $1,091, price is now CA $700 per person
CA $700
per person
Oct 7 - Oct 11
found 2 days ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
8.4/10 Very Good! (1,536 reviews)
Great area, room was nice but for some reason it was dusty. There was a layer of dust on the counter top beneath the tv and the side tables next to the bed. Other than that I really enjoyed the hotel! Perfect area, close enough to middle of downtown and walkable to petco park! Uber/lyft had no problems finding and picking us up either.

Reviewed on Aug. 26, 2025

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
Price was CA $1,510, price is now CA $821 per person
CA $821
per person
Nov 8 - Nov 15
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
8.2/10 Very Good! (1,385 reviews)
Exceptional pickleball courts. Great staff. Beautiful mountain views. Horrible internet.

Reviewed on Aug. 27, 2025

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Price was CA $1,394, price is now CA $898 per person
CA $898
per person
Oct 7 - Oct 11
found 2 days ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
9/10 Wonderful! (993 reviews)
Great staff & fun place!

Reviewed on Aug. 25, 2025

City24 Hotel Little Italy Mission Hills

City24 Hotel Little Italy Mission Hills

4.5 out of 5
Middletown
Price was CA $2,833, price is now CA $1,843 per person
CA $1,843
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
9.6/10 Exceptional! (85 reviews)
Great place to stay with my family of 9!!!

Reviewed on Aug. 21, 2025

InterContinental San Diego by IHG

InterContinental San Diego by IHG

4 out of 5
Downtown San Diego
Price was CA $1,774, price is now CA $1,172 per person
CA $1,172
per person
Oct 7 - Oct 11
found 2 days ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
9.2/10 Wonderful! (1,017 reviews)
No Fridge, easily get over charged for the mini bar. Never use the mini bar, but got charged after checked out without any notification.

Reviewed on Aug. 12, 2025

Ready to book your vacation to Winter Gardens?

 

Choose your dates

Winter Gardens Hotel Deals

Handlery Hotel

Handlery Hotel

3.5 out of 5
950 Hotel Cir N, San Diego, CA
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Aug 28 to Aug 29
CA $130
CA $149 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (1,998 reviews)
"Good location staff great pooland bar"

Reviewed on Aug. 25, 2025

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 CA $210 per night from Sep 1 to Sep 2
CA $210
CA $279 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (5,889 reviews)
Great view. Great location. Great shuttle.
"I had a really great time. The room could have been cleaner on arrival."

Reviewed on Aug. 24, 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 CA $173 per night from Sep 8 to Sep 9
CA $173
CA $199 total
Sep 8 - Sep 9
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 Aug. 24, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Winter Gardens

Chauffeured Adventure to Local San Diego Vineyards

Chauffeured Adventure to Local San Diego Vineyards

CA $339
per adult
100% of travellers recommend
Chauffeured Adventure to Local San Diego Vineyards
San Diego Mountain Hike Tour

San Diego Mountain Hike Tour

CA $95
per adult
San Diego Mountain Hike Tour
Tour Participants taking a moment to breathe

Guided Meditation and Mountain Hike Tour in San Diego

CA $80
per adult
Guided Meditation and Mountain Hike Tour in San Diego
See all activities in Winter Gardens

Frequently asked questions

How much does a Winter Gardens vacation package cost?
You can snap up a vacation package to this top destination from CA $700 on Expedia. But how much your vacation to Winter Gardens costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Winter Gardens?
To pick up cheap Winter Gardens vacation packages, organize your trip outside of peak times like public holidays and major events. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Winter Gardens?
Generally, a handful of days is enough to visit the major sights during your Winter Gardens vacation. But if you prefer to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Winter Gardens package deals?
Use Expedia's handy filters to help you find some unbeatable Winter Gardens package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Winter Gardens package deals in the off-peak season. Switch up your travel dates and you may score even better 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 break by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter Gardens?
If you're considering an impromptu Winter Gardens trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Winter Gardens?

  1. Pick your travel dates: What you want to do in Winter Gardens and your preferred season will help you decide when to travel.
  2. Budget wisely: Besides the price of your hotel, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Winter Gardens.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Winter Gardens. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Winter Gardens vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.