Lakeside Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Lakeside

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.4 out of 10, Exceptional, (123)
"It was an amazing place! Super clean and cozy."
haley c.
The price is AU$330
includes taxes & fees
19 Oct - 20 Oct
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Beachside Bliss: Steps to Beach + Hot Tub
2.0 star property
9.6 out of 10, Exceptional, (14)
"This property was a great house! The host was easy to communicate with and it was perfect for a little NYE getaway! "
maddie r.
The price is AU$673
includes taxes & fees
20 Oct - 21 Oct
Beachside Bliss: Steps to Beach + Hot Tub
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
9.4 out of 10, Exceptional, (30)
"House was very nice. Host was very responsive and kind."
Alyssa R.
The price is AU$591
includes taxes & fees
19 Oct - 20 Oct
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Heart of Historical Dist.*Parking*Claw Tub*A/C #4
10.0 out of 10, Exceptional, (7)
"Had a great stay here. Apartment was spacious and clean. Hosts responded quickly to questions. Would definitely stay again!"
Brett S.
The price is AU$322
includes taxes & fees
19 Oct - 20 Oct
Heart of Historical Dist.*Parking*Claw Tub*A/C #4
Heart of Historical Dist.*King*Parking*A/C*#1
10.0 out of 10, Exceptional, (2)
"Such a great stay. Close proximity to shopping and lake beach. The host is very professional and maintains a great property.Highly recommended the rental. "
Aaron M.
The price is AU$360
includes taxes & fees
19 Oct - 20 Oct
Heart of Historical Dist.*King*Parking*A/C*#1
The Boutique at Midtown Central / Hot Tub / Pet Friendly
9.6 out of 10, Exceptional, (10)
"We loved staying here. Jason was a great communicator and made sure our needs were met. Plenty of beds for our family of 8 adults. 10 minutes to the national park and its pristine beaches. "
Cindy W.
The price is AU$453
includes taxes & fees
21 Oct - 22 Oct
The Boutique at Midtown Central / Hot Tub / Pet Friendly
Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown
9.6 out of 10, Exceptional, (5)
"We really loved this house! Comfy beds, fun amenities (the converted garage hangout space is fabulous), great design/layout with plenty of room for everyone to spread out or all be together. The backyard was great, too! The location felt secluded, but everything is only a few minutes drive away."
Jeana H.
The price is AU$732
includes taxes & fees
19 Oct - 20 Oct
Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
9.8 out of 10, Exceptional, (12)
"We had a wonderful stay and girls weekend at this location, everything was so clean and perfectly accommodated all of our needs! Would recommend staying here if in the area again!"
Olivia D.
The price is AU$295
includes taxes & fees
21 Oct - 22 Oct
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Duplex | Firepit | Game Room | Hot Tub-all year
8.6 out of 10, Excellent, (17)
"Home very well stocked, very cute and clean inside. We're able to walk to restaurants and Sheridan beaches. Very friendly and safe area. Wine tasting, golfing and excellent restaurants nearby."
Marie H.
Duplex | Firepit | Game Room | Hot Tub-all year
Newely Remodeled Studio!
9.0 out of 10, Wonderful, (16)
"It was amazing and close by the dunes for our National Park and hiking day. Nice area with lots of restaurants around, and the place was super clean and cozy!"
JoC S.
The price is AU$244
includes taxes & fees
27 Oct - 28 Oct
Newely Remodeled Studio!
Romantic Cozy Home in "America’s Nicest Town"
9.8 out of 10, Exceptional, (14)
"Was the perfect location for our trip to Niles/Buchanan area "
Kathy J.
The price is AU$322
includes taxes & fees
20 Oct - 21 Oct
Romantic Cozy Home in "America’s Nicest Town"
Lake Breeze Stylish Beach Boho 1BD w/ Private Deck
10.0 out of 10, Exceptional, (11)
"Great property, and convenient access to the beach. Was perfect for me and my two teens. "
Kimberly N.
The price is AU$425
includes taxes & fees
5 Nov - 6 Nov
Lake Breeze Stylish Beach Boho 1BD w/ Private Deck
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach
10.0 out of 10, Exceptional, (1)
"Wonderful accommodations. Love the beach so the beach chairs was a nice surprise. Walking distance to many shops and restaurants."
Jay B.
The price is AU$406
includes taxes & fees
19 Oct - 20 Oct
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach
Breezy Pad, Close to the Lake, with Hot Tub
9.2 out of 10, Wonderful, (99)
"The house is just what it was described! We love it! Highly recommended "
The W.
The price is AU$285
includes taxes & fees
19 Oct - 20 Oct
Breezy Pad, Close to the Lake, with Hot Tub
Charming Cottage w/ HOT TUB - 5 Min from LAKE MICHIGAN!
9.6 out of 10, Exceptional, (5)
"Great stay near the beach and hiking, lots of good restaurants nearby, and the hot tub was just what we needed after some long outings"
Sam L.
The price is AU$331
includes taxes & fees
27 Oct - 28 Oct
Charming Cottage w/ HOT TUB - 5 Min from LAKE MICHIGAN!
Equipped Studio | Free Daily Breakfast, Indoor Pool + Fitness Center
2.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean, nice breakfast. No hot tub and remote for tv didnt work. Otherwise good. Amazingly clean. "
Amanda M.
The price is AU$287
includes taxes & fees
5 Nov - 6 Nov
Equipped Studio | Free Daily Breakfast, Indoor Pool + Fitness Center
Treehouse Bungalow- Quaint and Cozy Getaway!
8.6 out of 10, Excellent, (55)
"Very nice, comfortable stay"
Tina C.
The price is AU$637
includes taxes & fees
22 Oct - 23 Oct
Treehouse Bungalow- Quaint and Cozy Getaway!
The Moroccan Hideaway
10.0 out of 10, Exceptional, (2)
"We had such a wonderful stay! The place was cute, beautifully decorated, and had everything we needed for a comfortable weekend. The location was perfect—right downtown and close to all the restaurants, shops, and activities we wanted to enjoy. The host was fantastic and very attentive, which made the whole experience even better. We’d definitely stay here again and highly recommend it!"
Chris D.
The price is AU$534
includes taxes & fees
28 Oct - 29 Oct
The Moroccan Hideaway
The Loft Buchanan - Chic Industrial Loft in Historic Downtown
10.0 out of 10, Exceptional, (3)
"The property was extremely clean and perfectly described. Very cute inside. It was the perfect size for our group of 4 women. The loft was fine for us but might be difficult for some people to access. "
Kelly D.
The price is AU$398
includes taxes & fees
20 Oct - 21 Oct
The Loft Buchanan - Chic Industrial Loft in Historic Downtown
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!
9.0 out of 10, Wonderful, (22)
"Me and my family stayed here on Thanksgiving it was so comfortable and cozy any very clean l will definitely will book again checking in process was very easy!"
Melissa S.
The price is AU$807
includes taxes & fees
19 Oct - 20 Oct
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lakeside Hotel Reviews

Find out more about Lakeside

Everything you need to know about Lakeside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeside holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Lakeside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lakeside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lakeside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeside holiday rentals we have selected for you start as low as AU$285 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Lakeside rentals

At Expedia, we put the best Lakeside holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lakeside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Lakeside?

Yes, there are holiday rentals close to the most popular sights in Lakeside, or you can select a more secluded option if you're looking for a relaxing stay. Lakeside is known for its lake views and architecture. Make sure you have time to check out the forests and shopping during your trip.

What are some of the best holiday rentals that Lakeside has to offer?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: This holiday home rental outside of Lakeside is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Lakeside?

With 44 Expedia holiday rentals, you're guaranteed to find just the right place for your Lakeside stay.

What can I see and do in Lakeside?

Cultural attractions include Burnison Galleries, whereas Lake Michigan is a spot to enjoy nature. Eleanor O'Connor Wilson Woods Preserve and Edward and Elizabeth Leonard Wildlife Preserve are other places to visit while you're in town.

What are holiday rentals like in Lakeside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lakeside. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.