Lakeside Vacations from $492

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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!

The Latest Lakeside vacation packages

Price found within the past 48 hours. Click for updated prices.
Guesthouse Hotel at La Valle

Guesthouse Hotel at La Valle

4.5 out of 5
Save 100% on your flight
Price was $838, price is now $492 per person
$492
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.2/10 Wonderful! (140 reviews)
Nice

Reviewed on Jul 1, 2026

Los Bungalows

Los Bungalows

2.5 out of 5
Save 100% on your flight
Price was $1,138, price is now $630 per person
$630
per person
Sep 11 - Sep 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (538 reviews)

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,023, price is now $597 per person
$597
per person
Sep 4 - Sep 7
found 11 hours ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.6/10 Excellent! (2,287 reviews)
The lobby area is a bit dated and in need of update. Has a Starbucks right next door. Walking distance to Gaslamp district. We stayed in updated rooms on 7th floor. The were well updated but small. Rooms were clean and offered coffee and bottled water.

Reviewed on Jul 2, 2026

Shore House at The Del, LXR Hotels & Resorts

Shore House at The Del, LXR Hotels & Resorts

5 out of 5
Historic Downtown Coronado
Save 100% on your flight
Price was $3,077, price is now $1,874 per person
$1,874
per person
Sep 11 - Sep 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.2/10 Wonderful! (159 reviews)
The hotel was clean overall in both the public areas as well as the rooms. The staff was wonderful. Our only 2 issues, which is a big one for our family, were the beds and small rooms The beds were so uncomfortable & hard like a rock. The bedding was very flimsy . I have to make appointments with our chiropractor when we return home. Also, our room was very small and cramped. Other than those two issues, we enjoyed our stay.

Reviewed on Jul 1, 2026

Ocean Park Inn

Ocean Park Inn

3 out of 5
Pacific Beach
Save 100% on your flight
Price was $2,424, price is now $1,490 per person
$1,490
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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

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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)
This serene reservoir offers premier trout and catfish fishing in San Diego County's picturesque hills. Rent a motorboat to explore hidden coves or camp overnight with panoramic lake views.
See properties

What to do in Lakeside

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
Wine Tour Private San Diego County

Wine Tour Private San Diego County

$595
per traveler
Wine Tour Private San Diego County
See all activities in Lakeside

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
$182 nightly
The price is $211 total per night from Jul 6 to Jul 7
$211 total
Jul 6 - Jul 7
Total with taxes and fees
8.4/10 Very Good! (6,226 reviews)
"Beautiful views of Harbor, Nice pool, nice restaurant.."

Reviewed on Jul 1, 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
$341 nightly
The price is $392 total per night from Jul 6 to Jul 7
$392 total
Jul 6 - Jul 7
Total with taxes and fees
8.8/10 Excellent! (2,686 reviews)
"It was nice! We traveled with a small child and loved that it was so close to a calm beach with small waves. The pools were also nice and the rooms clean. The only two downsides was that they only had one sit down restaurant with not such amazing food and then a coffee bar in the morning, both overpriced ..."

Reviewed on Jul 2, 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
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $261 total per night from Jul 5 to Jul 6
$261 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (3,915 reviews)
"Amazing experience !"

Reviewed on Jul 2, 2026

Hard Rock Hotel San Diego
See all 9,432 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.

Find the Best Lakeside Vacation Packages

Lakeside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
San Diego Intl. Airport (SAN)
Population
20,600
Max Temp Winter
65ºF
Max Temp Summer
85ºF
Top Sights
Salerno Winery, Boomers El Cajon and Creation and Earth History Museum

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Frequently asked questions

How much does a Lakeside vacation package cost?
You can pick up a vacation package to this top destination from $492 on Expedia. But how much your vacation to Lakeside costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Lakeside?
September, October and December are great times to look for cheap Lakeside vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on flights and accommodations.
How many days is enough for Lakeside?
With a well-planned schedule, you can easily hit the main Lakeside sights in a handful of days. But if you prefer to discover hidden gems or take day trips, consider booking your Lakeside vacation for longer.
How to find the best Lakeside package deals?
Begin your search for a Lakeside package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Lakeside package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Lakeside escape off to a flying start.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Lakeside vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Lakeside?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Lakeside escape.
How to plan a trip to Lakeside?

  1. Pick your travel dates: What you want to do in Lakeside and your favorite season can help you decide when to go.
  2. Plan your budget wisely: Besides the price of your hotel, you should factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Lakeside.
  3. Discover Lakeside using our trip planning tool: Gain insights into the top attractions and best properties for your trip to Lakeside. You can also save your favorite places, collaborate with friends and family and organize your plans in one place.
  4. Decide how long to go away for: Now that you're up to speed on Lakeside, you can work out the right length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Lakeside vacation package for you.
  6. Add on excursions and experiences: Take a look at our travel guide to find some exciting things to do in Lakeside. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Lakeside vacation packages?
Secure your perfect escape to Lakeside with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until the next payday — we've teamed up with online lender Affirm to offer 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 extra charges, it's a breeze to stay on budget and snag great deals before they disappear.

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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.