Lakeside Holidays from £956

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Your Lakeside Holiday

When you choose a Lakeside holiday package, you can really enjoy your getaway to the fullest. Delve into the best things about this vibrant city knowing that everything has been worked out in advance. Fill your free time with tours of Four Winds Casino New Buffalo, Warren Dunes State Park and Warren Dunes State Park Beach, some of the things you shouldn't miss during your trip to Lakeside. Your dream Lakeside holiday is clicks away. Explore flights, hotels and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Lakeside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
11 Jun - 14 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (205 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
18 Jun - 21 Jun
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,896 reviews)
Nice hotel close to shopping and restaurants. Hotel restaurant breakfast buffet food was cold. Valet parking too expensive. Staff was nice and accommodating. Our floor was noisy with people partying on Friday night.

Reviewed on 8 May 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
per person
18 Jun - 21 Jun
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,197 reviews)
Good service and cleaning , the hotel is close to all principal areas of the city.

Reviewed on 10 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
11 Jun - 13 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago

Reviewed on 10 May 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
11 Jun - 13 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
7.8/10 Good! (1,013 reviews)
The property and the staff are great, I had a great experience. My toom had a great view, I will definitely be booking again.

Reviewed on 8 May 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
11 Jun - 14 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,124 reviews)
Need more pillows in the room.

Reviewed on 10 May 2024

Lakeside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
South Bend Intl. Airport (SBN)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Warren Dunes State Park, Warren Dunes State Park Beach and New Buffalo Public Beach

Our pick of the best 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, MI
Stay at this holiday home in Lakeside. Enjoy free WiFi, a garden and a patio. Popular attractions Four Winds Casino New Buffalo and Burnison Galleries are located ...
9.2/10 Wonderful! (30 reviews)
Great place & great hosts
"We had a great time, the place was beautiful and the hosts were very nice and caring. We will definitely be back in the summer."

Reviewed on 17 Oct 2023

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, MI
Stay at this family-friendly cottage in Lakeside. Enjoy free WiFi, private pools and a garden. Popular attractions Four Winds Casino New Buffalo and Burnison ...
9.2/10 Wonderful! (44 reviews)
Wonderful experience
"We were really dedicated to hosting our families in a shared, yet private space, and we were not disappointed. From walks on the beach to dinners in town, this place has it all. The houses are comfortable and inviting with all amenities, and our host was kind and thoughtful in our communications. ..."

Reviewed on 12 Apr 2024

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, MI
Stay at this holiday home in Lakeside. Enjoy an in-room coffee maker, an in-room fireplace and air conditioning. Popular attractions Four Winds Casino New Buffalo ...
9.4/10 Exceptional! (10 reviews)
My birthday
"Everything was amazing!! I would recommemd highly and stay again!! ONLY thing i can recommend is a bigger water heater as the hot water ran out fast. But seriously so relaxing and amazing worth the money for a perfect get away!!"

Reviewed on 28 Apr 2024

Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI beach
See all 1,740 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Lakeside holiday with Expedia?
Choose Expedia to plan your next adventure easily and all in one place. Our top tip for bagging the best deal on a Lakeside retreat? Bundle your flights, accommodation and/or hire car into a package holiday. Then add some fun tours and activities. Most bookings also include flexible cancellation policies, so there’s no need to panic if you have to switch up your itinerary. Round-the-clock assistance with cancelling and amending your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Lakeside?
Lakeside draws the crowds in May, June and July. If you want a more relaxed holiday, head there in November, December and January. With average daytime temperatures of -3ºC, January is the coolest month in Lakeside. The warmest month is July, when you can experience averages of 22ºC throughout the day. Whatever the weather conditions, you’ll discover loads to keep you entertained here.
What is the top hotel for my holiday in Lakeside?
Offering many of home’s creature comforts, Comfort Suites Stevensville - St. Joseph will make an ideal base for your Lakeside holiday.
How do I get a cheap holiday to Lakeside?
Creating your own Lakeside holiday with Expedia is a simple way to save. We have over 400 air carriers and 321,000 hotel options throughout the world. With such a broad range to pick from, you’ll have no difficulty creating your dream adventure. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Lakeside holiday?
Make sure your next holiday in Lakeside is a memorable one by taking in its major attractions. Four Winds Casino New Buffalo, New Buffalo Public Beach, Warren Dunes State Park Beach and Michiana Beach are just some of the things we recommend seeing while you’re in this city.
What is the best area to stay in when on holiday in Lakeside?
If you plan to check out Burnison Galleries, save yourself the hassle of commuting and find somewhere to stay close by. It’s one of the most popular attractions in Lakeside.
Do I need a visa for my Lakeside holiday?
Research the latest rules on official government websites. Your nationality and whether you’re visiting for study, leisure or business will determine if you’ll require a visa for Lakeside. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow enough time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Lakeside holiday?
Though everyone’s style is different, it can be helpful to have a few guidelines for what kind of clothes to wear on your holiday in Lakeside. We recommend browsing style blogs before you head off for inspiration on local fashion trends. Daytime temperatures during January, Lakeside’s coolest month, average around -3ºC. July marks this destination’s warmest month when the average temperature reaches 22ºC. Our suggestion? Take the guesswork out of packing and check the local weather conditions.
What does an Expedia Lakeside holiday include?
It depends on what sort of trip you’re planning. Lakeside travel deals can include hotels, car hires and flights. You can mix and match to create the package that suits your budget and style. You can also add on activities and experiences after you’ve booked to score even bigger discounts. Explore a large selection of property types and pick one that suits the size of your group. The most in-demand rentals here are private holiday homes and cottages. With Expedia, it’s easy to design your Lakeside escape however you like.
Does Expedia offer Book Now, Pay Later Lakeside holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits you best during checkout and take the stress out of budgeting for your trip. Make sure you bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying across multiple transactions sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
  • No-deposit holidays: Hitting the “book now” button is easier with this plan. With no deposit required for your getaway, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with a Lakeside Expedia holiday?
Yes, you’re in control. Expedia has access to more than 400 airlines around the world, so you can tailor your Lakeside holiday according to your travel preferences.

Discover the most popular places to visit in Lakeside

Image for Burnison Galleries

Burnison Galleries

You can spend an afternoon browsing 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. Flight-inclusive packages are ATOL protected.