Lakeside Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Your Lakeside Vacation

Reserve a Lakeside vacation package and get ready to experience the best of this lively city. Consider staying in the neighborhood of Lake Murray, which is good for golfing, views and families. The Magnolia, Santee Lakes and Shadow Mountain Community Church are just a few of the sights worth visiting during your trip to Lakeside. Stop dreaming and start traveling. Check out the many options on Expedia today and finally put your Lakeside vacation plans into motion!

Top Lakeside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Z

Hotel Z

3 out of 5
Downtown San Diego
Price was CA $1,655, price is now CA $1,111 per person
CA $1,111
per person
Jan 9 - Jan 13
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
9.2/10 Wonderful! (1,212 reviews)
Staff super nice and helpful. Room clean and quiet. Bed super comfy! Perfect location

Reviewed on Nov 8, 2026

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was CA $2,138, price is now CA $1,233 per person
CA $1,233
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
8.8/10 Excellent! (2,743 reviews)

Estancia La Jolla Hotel & Spa

Estancia La Jolla Hotel & Spa

4 out of 5
La Jolla Farms
Price was CA $2,952, price is now CA $1,967 per person
CA $1,967
per person
Dec 17 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Diego (SAN)
9/10 Wonderful! (460 reviews)

Fairmont Grand Del Mar

Fairmont Grand Del Mar

5 out of 5
Carmel Valley
Price was CA $2,404, price is now CA $1,610 per person
CA $1,610
per person
Jan 11 - Jan 14
found 1 hour ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
9.4/10 Exceptional! (1,000 reviews)
Excellent property and stay

Reviewed on Nov 6, 2026

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Price was CA $1,862, price is now CA $1,291 per person
CA $1,291
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
9/10 Wonderful! (1,585 reviews)

Ready to book your vacation to Lakeside?

 

Choose your dates

Lakeside 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
The price is CA $198 per night from Nov 22 to Nov 23
CA $198
CA $279 total
Nov 22 - Nov 23
includes taxes & 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
The price is CA $252 per night from Dec 9 to Dec 10
CA $252
CA $361 total
Dec 9 - Dec 10
includes taxes & fees
9/10 Wonderful! (4,587 reviews)
"Amazing hotel! Staff was amazing and very friendly and helpful! Great location too!"

Reviewed on Nov 8, 2026

Hard Rock Hotel San Diego
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 $128 per night from Dec 1 to Dec 2
CA $128
CA $147 total
Dec 1 - Dec 2
includes taxes & fees
Handlery Hotel
See all 9,445 properties in Lakeside
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

Stay near popular Lakeside attractions

A calm lake with a boat, surrounded by lush greenery and mountains in the background.

Lake Jennings

9.0/10 (2 reviews)
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.
See properties

What to do in Lakeside

San Diego: Guided Natural History Walk

San Diego: Guided Natural History Walk

CA $91
per adult
San Diego: Guided Natural History Walk
Wine Tour Private San Diego County

Wine Tour Private San Diego County

CA $986
per traveller
Wine Tour Private San Diego County
See all activities in Lakeside

Frequently asked questions

How much does a Lakeside vacation package cost?
Offering great value package deals from CA $1,111 on Expedia, you'll be thrilled with how little a vacation to Lakeside costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Lakeside?
To pick up cheap Lakeside vacation packages, organize your getaway outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Lakeside?
Allow at least 4 days for your Lakeside vacation if you want to immerse yourself in all that makes this place special. Stroll around key neighbourhoods, including Crest and Fletcher Hills. Then tick off major sights like Lake Jennings and Carlton Oaks Country Club. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Lakeside? Consider squeezing in an excursion or two.
How to find the best Lakeside package deals?
Use Expedia's filters to find some great Lakeside package deals. When you begin 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 trip for midweek, or search for Lakeside package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Lakeside vacation as a package?
You can enjoy significant savings on your Lakeside retreat by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat 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 Lakeside?
If you're planning an impromptu Lakeside getaway, 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 awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Lakeside?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Lakeside.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when calculating how much to save for your trip to Lakeside. Then, pick a property that works with your budget, whether that's a low-cost option or a lavish getaway.
  3. Decide your trip length: Consider how long you'd like to spend discovering Lakeside. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the perfect Lakeside vacation package for you.

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