Book Holiday Homes in Lakeside

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Featured Holiday Homes in Lakeside

Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!

Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!

Lakeside
Stay at this vacation home in Lakeside. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Four Winds Casino New Buffalo and Burnison Galleries ...
Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
Breezy Pad, Close to the Lake, with Hot Tub

Breezy Pad, Close to the Lake, with Hot Tub

St Joseph
The price is NZ$361 per night from 1 Apr to 2 Apr
NZ$361
includes taxes & fees
1 Apr - 2 Apr
Book a stay at this golf vacation home in Saint Joseph. Enjoy free WiFi, a garden, and patios. Popular attractions Silver Beach and Box Factory for the Arts ...
Breezy Pad, Close to the Lake, with Hot Tub
Sweet Stay By-The-Lake in Michigan City with AC, WiFi

Sweet Stay By-The-Lake in Michigan City with AC, WiFi

2 out of 5
Michigan City
Stay at this vacation home in Michigan City. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Blue Chip Casino and Canada Park ...
Sweet Stay By-The-Lake in Michigan City with AC, WiFi
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Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub

Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub

New Buffalo
Stay at this vacation home in New Buffalo. Enjoy a garden, patios, and in-room fireplaces. Popular attractions Four Winds Casino New Buffalo and Blue Chip Casino ...
Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub
Pool Vibes Retreat | Hot Tub | Poker | Fire Pit

Pool Vibes Retreat | Hot Tub | Poker | Fire Pit

Stevensville
Stay at this vacation home in Stevensville. Enjoy private pools, a garden, and an in-room coffeemaker. Popular attractions Silver Beach and Grand Mere State ...
Pool Vibes Retreat | Hot Tub | Poker | Fire Pit
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Michigan City
Book a stay at this family-friendly vacation home in Michigan City. Enjoy tennis courts, a pool table, and patios. Popular attractions Blue Chip Casino and Waterfall ...
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Game Room, 4 Min to Warren Dunes, Fire Pit and More!

Game Room, 4 Min to Warren Dunes, Fire Pit and More!

Sawyer
Stay at this vacation home in Sawyer. Enjoy patios and air conditioning. Popular attractions Warren Dunes State Park Beach and Cherry Beach are located ...
Game Room, 4 Min to Warren Dunes, Fire Pit and More!
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13

Michigan City
Book a stay at this beach vacation home in Michigan City. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Blue Chip Casino and Putting Green ...
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

New Buffalo
Book a stay at this golf vacation home in New Buffalo. Enjoy free WiFi, private pools, and a garden. Popular attractions Four Winds Casino New Buffalo and Local ...
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
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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.

Lakeside Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Lakeside vacation homes are the perfect way for you to wing it.

Holiday houses in Lakeside let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Lakeside in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Lakeside adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Lakeside with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Lakeside vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Lakeside Holiday Homes essential information

Accommodation
1072 Holiday Homes
Lowest Price
NZ$201
Highest Price
NZ$361
Popular accommodation
Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!, Breezy Pad, Close to the Lake, with Hot Tub, Sweet Stay By-The-Lake in Michigan City with AC, WiFi, Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub, Pool Vibes Retreat | Hot Tub | Poker | Fire Pit, Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart, Game Room, 4 Min to Warren Dunes, Fire Pit and More!, BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13, Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

Top trending hotels in Lakeside

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
Stay at this vacation home in Lakeside. Enjoy free WiFi, a garden, and patios. Popular attractions Four Winds Casino New Buffalo and Burnison Galleries are located ...
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
Book a stay at this family-friendly cottage in Lakeside. Enjoy free WiFi, private pools, and a garden. Popular attractions Four Winds Casino New Buffalo and ...
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
The price is NZ$244 per night from 1 Apr to 2 Apr
NZ$244
includes taxes & fees
1 Apr - 2 Apr
Stay at this 3.5-star spa hotel in Michigan City. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
Blue Chip Casino Hotel and Spa
Save an average of 15% on thousands of hotels when you're signed in
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road, New Buffalo, MI
Fully refundable
The price is NZ$201 per night from 1 Apr to 2 Apr
NZ$201
includes taxes & fees
1 Apr - 2 Apr
Stay at this 3.5-star business-friendly hotel in New Buffalo. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
Four Winds Casino Resort – New Buffalo
Don't see what you're looking for?
See all available properties in Lakeside
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.