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

This weekend
Next weekend

Holiday Rentals in Lakeside

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside
9.2 out of 10, Wonderful, (66)
"Great rental for multiple families. It was terrific having a pool and the beach was wonderful and close by."
United States
Renay S.
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Lakeside
9.0 out of 10, Wonderful, (50)
"This is our second time renting Carrie's Cottage and we absolutely love it. Perfect location to visit all the cute towns in this part of Michigan, walking distance to a beautiful beach, and plenty of space for adults and young children. We hope to be back again!"
United States
Marthe G.
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

The Neighborhood Hotel - Grand Beach

4.0 star property
New Buffalo
9.6 out of 10, Exceptional, (65)
"Absolutely perfect, we loved every bit of our stay!"
United States
Rebecca
The Neighborhood Hotel - Grand Beach

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Michigan City
9.6 out of 10, Exceptional, (121)
"We enjoyed everything about the house it could have used a little weed eating but other than that it was perfect my family enjoyed their stay Thank you again"
United States
Barb W.
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

New Buffalo
10.0 out of 10, Exceptional, (79)
"The house was perfect for our family vacation with the pool and location!! Better than advertised. "
United States
Michael D.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

2.0 star property
Sawyer
10.0 out of 10, Exceptional, (28)
"House was perfect for our multi family family vacation! Amenities were wonderful and its clear that Tim is passionate about hosting a wonderful saty for all his guests! "
United States
Kristy D.
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Michigan City
9.8 out of 10, Exceptional, (150)
"The house was a great location. Close to the beach. We had a wonderful time!"
United States
Jim W.
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Michigan City
9.4 out of 10, Exceptional, (126)
"Was as described great stay"
United States
Amber C.
The price is AU$292
includes taxes & fees
4 Dec - 5 Dec
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Michigan City
9.6 out of 10, Exceptional, (245)
"House had everything we needed, great resort neighborhood for kids "
United States
Kathryne I.
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Michigan City
10.0 out of 10, Exceptional, (244)
"Great place to stay with a big family "
United States
Larry Y.
Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Breezy Pad, Close to the Lake, with Hot Tub

St Joseph
9.2 out of 10, Wonderful, (106)
"We stayed at the Breezy pad for a family vacation and it was wonderful. We were able to bring our dog with and the house was very dog and family friendly. We loved that it was close to plenty of beaches and the neighborhood was very family friendly and quiet. We will definitely be making this a yearly family vacation. "
United States
Anna E.
The price is AU$254
includes taxes & fees
4 Dec - 5 Dec
Breezy Pad, Close to the Lake, with Hot Tub

Pool Vibes Retreat | Hot Tub | Poker | Fire Pit

Stevensville
10.0 out of 10, Exceptional, (5)
"Great time, very clean and well maintained "
United States
Jake H.
Pool Vibes Retreat | Hot Tub | Poker | Fire Pit

New luxury home steps to downtown w/yr round heated pool

Downtown New Buffalo
10.0 out of 10, Exceptional, (32)
"Wonderful property in the heart of New Buffalo. Our third time there and will be back again next summer. House is stunning, has every amenity imaginable and Heather is a fantastic host!"
United States
Nancy L.
New luxury home steps to downtown w/yr round heated pool

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Michigan City
8.8 out of 10, Excellent, (23)
"Good location great pool host was nice to deal with. Had a good time"
United States
T H.
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Union Pier
10.0 out of 10, Exceptional, (134)
"Very comfortable, steps to a dock, use of canoe, fishing, hot tub, Firepit for roasting marsh mellows. Very pleasant stay."
United States
Kenneth
Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Sunset Dunes Vacation Villas

3.0 star property
Bridgman
9.6 out of 10, Exceptional, (12)
"The apartment was wonderful, close to the Red Bud Race track, restaurants, and of course, the beach! We would definitely stay here again. "
United States
NANCY
Sunset Dunes Vacation Villas

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

New Buffalo
9.2 out of 10, Wonderful, (70)
"Great backyard space to hang out. Awesome location to walk and explore the area and an easy drive to other spots along the lake. The few minor issues we had were quickly communicated and addressed with the owner, so the trip went on without a hitch."
United States
Laura P.
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Michigan City
8.6 out of 10, Excellent, (88)
"This place has a beautiful view over housetops of the lake. Lots of seating on two decks for the view. Plenty of parking.The house accommodated our group of 15, with spaces to eat, put together a puzzle, play board games and be in the same area. A short walk to the beach. The host answered our questions quickly before arrival. The place is older but clean. The kitchen was supplied with nice pans and basic dishes."
United States
Marilyn H.
The price is AU$680
includes taxes & fees
8 Dec - 9 Dec
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

New Buffalo
9.4 out of 10, Exceptional, (12)
"We were pleased with all amenities at the house. Wish beach on Lake Michigan had been easier to access."
United States
Glenda F.
Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Michigan City
10.0 out of 10, Exceptional, (119)
"The place was even better than the photos. It was a great place to stay."
United States
Alex B.
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
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.

Black Friday Sale

Save up to 40% on select hotels
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$254 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?

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.: This holiday home rental outside of Lakeside offers a balcony, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.