Lakeside Holiday Rentals

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Our top choices for Lakeside holiday rentals

9.4 out of 10, Exceptional, (126)
"Was as described great stay"
United States
Amber C.
The price is NZ$324
includes taxes & fees
26 Dec - 27 Dec
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great option for a quick weekend trip to the Dunes. Clean, comfy and good communication from the host."
United States
Dillon K.
The price is NZ$467
includes taxes & fees
28 Dec - 29 Dec
Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex
9.8 out of 10, Exceptional, (14)
"It was very cozy and perfect! "
United States
Tommy W.
The price is NZ$278
includes taxes & fees
28 Dec - 29 Dec
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
10.0 out of 10, Exceptional, (1)
"Very clean, nice breakfast. No hot tub and remote for tv didnt work. Otherwise good. Amazingly clean. "
United States
Amanda M.
The price is NZ$255
includes taxes & fees
2 Jan - 3 Jan 2026
Equipped Studio | Free Daily Breakfast, Indoor Pool + Fitness Center
8.6 out of 10, Excellent, (17)
"Nice rental with lots of fun extras. Had a great time in the game room, hot tub and fire pit. Great neighborhood. The property condition was ok. Not very clean. "
United States
Andrea
The price is NZ$350
includes taxes & fees
28 Dec - 29 Dec
Duplex | Firepit | Game Room | Hot Tub-all year
9.8 out of 10, Exceptional, (14)
"Was the perfect location for our trip to Niles/Buchanan area "
United States
Kathy J.
The price is NZ$364
includes taxes & fees
19 Jan - 20 Jan 2026
Romantic Cozy Home in "America’s Nicest Town"

Holiday Home in Downtown New Buffalo

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
10.0 out of 10, Exceptional, (29)
"It was a lovely stay! Very clean and it was awesome I could take my dog with me :)"
United States
Roxie
The price is NZ$518
includes taxes & fees
7 Jan - 8 Jan 2026
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
8.6 out of 10, Excellent, (4)
"Good house and good location. Lots of space"
United States
Todd K.
The price is NZ$744
includes taxes & fees
28 Dec - 29 Dec
5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022
9.4 out of 10, Exceptional, (33)
"Nice"
United States
Maryellen W.
The price is NZ$646
includes taxes & fees
5 Jan - 6 Jan 2026
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
10.0 out of 10, Exceptional, (16)
"Cozy house close to New Buffalo. Yard was great and game room was great additional space to hang out in. Would definitely go back!"
United States
Liz W.
The price is NZ$529
includes taxes & fees
5 Jan - 6 Jan 2026
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
9.2 out of 10, Wonderful, (109)
"Great location"
United States
Anonymous traveller
The price is NZ$307
includes taxes & fees
4 Jan - 5 Jan 2026
Breezy Pad, Close to the Lake, with Hot Tub

Cabin in Berrien Springs

Secluded Country Cabin
10.0 out of 10, Exceptional, (74)
"We thoroughly enjoyed our stay. Charming, family-friendly and with gracious hosts. Check-in and check-our was a breeze. Thank you!"
United States
Joshua J.
The price is NZ$324
includes taxes & fees
28 Dec - 29 Dec
Secluded Country Cabin
2.0 star property
The price is NZ$304
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Michigan City Getaway-Private-Unit A
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."
United States
Jay B.
The price is NZ$467
includes taxes & fees
7 Jan - 8 Jan 2026
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

Holiday Home in Baroda

Scenic Southwest Michigan Awaits!
10.0 out of 10, Exceptional, (132)
"Amazing location, beautiful home, clean, quiet neighborhood. Very happy with the stay will definitively be going back! "
United States
Kyle C.
The price is NZ$317
includes taxes & fees
5 Jan - 6 Jan 2026
Scenic Southwest Michigan Awaits!
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. "
United States
Aaron M.
The price is NZ$446
includes taxes & fees
22 Jan - 23 Jan 2026
Heart of Historical Dist.*King*Parking*A/C*#1
10.0 out of 10, Exceptional, (4)
"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. "
United States
Kelly D.
The price is NZ$437
includes taxes & fees
4 Jan - 5 Jan 2026
The Loft Buchanan - Chic Industrial Loft in Historic Downtown
2.0 star property
The price is NZ$463
includes taxes & fees
26 Dec - 27 Dec
Classic One-Bedroom apartment with King Bed
10.0 out of 10, Exceptional, (7)
"This was the perfect place for a weekend getaway! Convenient location, clean apartment, and very responsive hosts. You can tell they put in a lot of effort and passion into their property. "
United States
Danielle S.
The price is NZ$393
includes taxes & fees
26 Dec - 27 Dec
Heart of Historical Dist.*Parking*Claw Tub*A/C #4
10.0 out of 10, Exceptional, (50)
"Everything & more you could ever need for a quiet retreat! "
United States
Elsa H.
The price is NZ$746
includes taxes & fees
3 Jan - 4 Jan 2026
Area Favorite- 2 Bedroom, Game Room, Fall Bonfires
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.
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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 favorite 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 depends 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 NZ$307 per night. Entering your travel dates in the search wizard you might find 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?

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants : This holiday home rental outside of Lakeside is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 patio, a terrace and a garden so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Lakeside?

With 45 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.