Lakeside Vacation Packages

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Your Lakeside Vacation

With a Lakeside vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your journey has been taken care of before you depart, so you can make the most of your time discovering this exciting city. Fill your schedule with tours of Four Winds Casino New Buffalo, New Buffalo Public Beach and Warren Dunes State Park Beach, some of the attractions you shouldn't miss during a trip to Lakeside. Browse Expedia's wide range of travel options and start planning your dream vacation to Lakeside today.

Top Lakeside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Nov. 9 - Nov. 11
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very Good! (1,321 reviews)
The location is great, right on the river. The rooms are a bit outdated. The staff wasn’t as friendly as I’m used to for a 4 star hotel. They also charge a daily fee. It can be used for room service but everything is pretty pricey and there’s a $5 delivery fee which I didn’t notice until after ordering.

Reviewed on Sep. 24, 2024

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
Nov. 14 - Nov. 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.8/10 Excellent! (1,902 reviews)
I likes the view, the building and the staff. I Wish the casual happy hour had more breakfast choices.

Reviewed on Sep. 25, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Nov. 14 - Nov. 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,365 reviews)
Stunning hotel with exceptional staff.

Reviewed on Sep. 23, 2024

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
Nov. 14 - Nov. 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.6/10 Excellent! (1,532 reviews)
I like the property. I just wish it was better staffed when they had bigger events in the lobby other than that it was a great time.

Reviewed on Sep. 23, 2024

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Nov. 14 - Nov. 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (516 reviews)
The hotel has only been open for a few months and staff was very welcoming. Excellent breakfast options.

Reviewed on Sep. 26, 2024

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Lakeside Hotel Deals

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Lakeside
9/10 Wonderful! (40 reviews)
Perfect escape with pets
"This was a 4 day getaway to relax. While there is no water view from the property, a short walk and some steps led us to the perfect semiprivate beach. There were umbrellas, chairs and 2 kayaks available to use. Despite it being mid September, the water was swimmable and the temps were high 80s. ..."

Reviewed on Sep. 18, 2024

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Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside
9.2/10 Wonderful! (44 reviews)
Lovely winter getaway
"Despite the frigid cold we enjoyed our stay in cabin A. It was clean, comfortable, and well equipped. Frank was great: when there was the chance we would have to cancel due to the weather, he suggested a change of plans and accommodated us."

Reviewed on Jan. 18, 2024

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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI beach
Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI beach
Union Pier
9/10 Wonderful! (21 reviews)
Perfect beach house
"Perfect place to stay if youre looking to relax at a beautiful beach nearby."

Reviewed on Aug. 30, 2024

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Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI beach
See all 1,756 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

Frequently asked questions

How much does a Lakeside vacation package cost?
We make it simple for everyone to travel, with Lakeside vacation packages starting from just CA $625. You’ll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate escape, why not add a few experiences and tours to your travel itinerary?
How do I get a cheap travel package to Lakeside?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we’ve got everything you need. Pick and choose the combination that best fits you and see your savings grow. We know a travel package is never a one-size-fits-all. That’s why Expedia offers over 550 air carriers and 1,000,000 hotels around the globe, which lets you customize your Lakeside vacation.
Where should I stay in Lakeside?
With lots to explore in Lakeside, it’s a good idea to lock in a hotel near its attractions. Cherry Beach, St. Julian Winery - Union Pier Tasting Room and Round Barn Union Pier Tasting Room are some interesting ones to put on your itinerary.
What are the top hotels in Lakeside?
If it’s your first time in Lakeside, secure a room at New, Modern 6 Bd Home With Private Pool or 3 Nt Min - Lakeside Home Walking Distance To Association Beach. Both offer comfy beds and are favorites among many savvy travelers.
How far in advance should I book my Lakeside vacation?
Smart travelers will likely want to book as early as possible. You can generally compare international airfares on Expedia up to 12 months before your intended flight. If you’re purchasing your ticket at the last minute, don’t worry. Low prices occasionally appear in the last weeks before departure dates.
What does an Expedia Lakeside travel package include?
Expedia has all you need to lock in Lakeside trip, but how your package is structured is entirely up to you. Select from a combination of hotels, rental cars and flights. Looking for a few activities to keep you on the move? Once you’ve made your booking, you can add them too. No matter your style, there’s a deal to suit your needs.
What should I know before booking a Lakeside travel package?
Discover deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we have them all. You’ll save precious dollars just for combining your bookings. Whether you’re taking off on a snow and ski adventure or sipping cocktails on a beach, your perfect getaway is just clicks away.
Can I choose my airline with a Lakeside Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to pick from globally. With so much choice, finding the ideal carrier to take you to Lakeside won’t be hard.
If I'm not able to travel, can I cancel my Lakeside vacation package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel and rebook your Lakeside vacation package for free if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company for older bookings. If life throws you a curveball, look up our Customer Service Portal for further information.

Discover the most popular places to visit in Lakeside

Image for Burnison Galleries

Burnison Galleries

You can spend time studying the exhibits at Burnison Galleries in Lakeside. Stroll along the beautiful beaches or visit the casinos in this romantic area.

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