Lakeside Holidays from £719

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Your Lakeside Holiday

With a Lakeside holiday 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 holiday to Lakeside today.

Top Lakeside Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Not worth it for the money. Good location but nothing special.

Reviewed on 8 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 6 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
The hotel is well located, walkable to magnificent mile, shops, restaurants and the River. The spacious room was on a high floor with high ceilings and an incredible view. The amenities were very nice and the room was impeccable.

Reviewed on 8 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on 8 Nov 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,079, price is now £841 per person
£841
per person
11 Jan - 16 Jan
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,202, price is now £955 per person
£955
per person
20 Jan - 24 Jan
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,309 reviews)

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

Top hotels in Lakeside

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
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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI
10/10 Exceptional! (152 reviews)
"This was a beautiful property. It truly is unique and one of a kind. I would like to go back in the summer and enjoy the screened in cottage a little bit more. The area is beautiful, and we went at the perfect time of year to see all the leaves change, the weather was outstanding. Truly everything ..."

Reviewed on 6 Nov 2026

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Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is £77 per night from 10 Nov to 11 Nov
£77
10 Nov - 11 Nov
includes taxes & fees
Four Winds Casino Resort – New Buffalo
See all 1,909 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

Stay near popular Lakeside attractions

Burnison Galleries

Burnison Galleries showcases diverse works from regional artists in a welcoming Lakeside setting. Browse the curated collection at your leisure, with no admission fee required for this cultural Michigan experience.
See properties

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.

* 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.