Lakeside Vacation Packages

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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.
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 $1,533, price is now CA $1,081 per person
CA $1,081
per person
Aug 20 - Aug 24
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Diego (SAN)
8.4/10 Very good! (1,892 reviews)
This is our 4th year coming to the Hyatt Regency - Welk Resort. This is an outstanding place to staycation, or vacation, as a family. There are so many amenities to accommodate the stay, including; pools, spas, water slides, snack bars, market and places to dine. The grounds are upbeat daily and Staff is the best. The rooms are great but I recommend the Villas. We'll be back next year.

Reviewed on Jul 3, 2026

Hilton San Diego/Del Mar

Hilton San Diego/Del Mar

4 out of 5
Del Mar Heights
Price was CA $2,158, price is now CA $1,479 per person
CA $1,479
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to San Diego (SAN)
8.6/10 Excellent! (1,004 reviews)
This hotel is a little older than expected.

Reviewed on Jun 27, 2026

Ocean Park Inn

Ocean Park Inn

3 out of 5
Pacific Beach
Price was CA $3,308, price is now CA $2,267 per person
CA $2,267
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to San Diego (SAN)
9.4/10 Exceptional! (1,002 reviews)
This was a great hotel to stay at. It was a perfect location, view was great, staff extremely friendly and helpful and room was perfect . Would definitely stay here again.

Reviewed on Jul 2, 2026

Omni La Costa Resort & Spa Carlsbad

Omni La Costa Resort & Spa Carlsbad

4 out of 5
La Costa
Price was CA $1,866, price is now CA $1,315 per person
CA $1,315
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Calgary (YYC) to San Diego (SAN)
8.2/10 Very good! (1,009 reviews)
We absolutely loved our stay! Everything was clean and the staff was incredibly kind. We would definitely stay here again!

Reviewed on Jul 3, 2026

Urban Boutique Hotel

Urban Boutique Hotel

3 out of 5
Downtown San Diego
Price was CA $1,708, price is now CA $1,214 per person
CA $1,214
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
8.6/10 Excellent! (1,253 reviews)
I didn't like my room. I felt I was mislead in what I was expecting to get. Especially for the price the room was to small to even move around in, the bathroom. And no where to sit down. Not comfortable at all. We were supposed to stay 4 days and 3 nights We thought we were going to check in on Friday. But instead we checked in on Saturday the day of my event. And checked out Sunday. And didn't stay til Monday. I was ready to go.

Reviewed on Jul 4, 2026

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Lakeside Hotel Deals

Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
1355 N Harbor Drive San Diego CA
The price is CA $229 per night from Jul 6 to Jul 7
CA $229
CA $315 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very good! (6,237 reviews)
"Convenient location to the Convention Center, Padres games, Gas lamp district and Bayfront shops and attractions."

Reviewed on Jul 3, 2026

Wyndham San Diego Bayside
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
The price is CA $419 per night from Jul 7 to Jul 8
CA $419
CA $557 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (2,699 reviews)
"Good"

Reviewed on Jul 4, 2026

Paradise Point Resort & Spa
Hard Rock Hotel San Diego

Hard Rock Hotel San Diego

4 out of 5
207 5th Ave San Diego CA
The price is CA $236 per night from Jul 19 to Jul 20
CA $236
CA $342 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,935 reviews)
"I had the most unique experience and enjoyed the great scenery"

Reviewed on Jul 4, 2026

Hard Rock Hotel San Diego
See all 9,434 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
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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

Wine Tour Private San Diego County

Wine Tour Private San Diego County

CA $821
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 $1,081 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.

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