Lakeside Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 8 - Aug 9
Tomorrow
Aug 9 - Aug 10
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Lakeside

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

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

9.2 out of 10, Wonderful, (63)
"this was a great place needed to have some cast iron skillets rather than the other pans thank you for letting us enjoy your place "
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
The Neighborhood Hotel - Grand Beach
Suite 1 - Three Bedroom | 3 bedrooms, premium bedding, memory foam beds, blackout drapes

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (55)
"Had a wonderful stay at cottage 13, all necessary amenities were available and nice quaint location. Very nice stay overall. "
The Neighborhood Hotel - Grand Beach
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
Outdoor dining

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

10.0 out of 10, Exceptional, (72)
"This house is a great setup and well taken care of. The owners are very responsive and location is close to everything."
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
Sunset Dunes Vacation Villas
Standard Villa | Private kitchenette | Fridge, microwave, oven, stovetop

Sunset Dunes Vacation Villas

3.0 star property
10.0 out of 10, Exceptional, (8)
"This is an attractive, comfortable, well-maintained, and conveniently located rental. We enjoyed our stay and would stay here again."
Sunset Dunes Vacation Villas
Walkable cozy cottage, Outlet Mall across street!
Interior

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (17)
"Loved the cottage it had everything we needed very nice!"
The price is ￥16,810
￥45,447 total
includes taxes & fees
Sep 3 - Sep 4
Walkable cozy cottage, Outlet Mall across street!
Cozy Cottage with view of Lake Michigan
Fridge, microwave, oven, stovetop

Cozy Cottage with view of Lake Michigan

10.0 out of 10, Exceptional, (45)
"A very nice little house near the lake. Greg is a great host."
Cozy Cottage with view of Lake Michigan
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
A heated pool

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

10.0 out of 10, Exceptional, (194)
"We loved our stay here. I can’t wait to come back in the summer months"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Property grounds

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

9.4 out of 10, Exceptional, (116)
"Very nice relaxing stay. "
The price is ￥18,368
￥35,384 total
includes taxes & fees
Sep 2 - Sep 3
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach nearby

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"Unsafe parking, uncomfortable couch and beds. We didn’t stay the night due to the poor conditions."
The price is ￥39,542
￥64,366 total
includes taxes & fees
Aug 10 - Aug 11
Treehouse Bungalow- Quaint and Cozy Getaway!
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Terrace/patio

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

10.0 out of 10, Exceptional, (168)
"This property is beautiful with a lot of space, bedrooms, and bathrooms. The location was perfect for walking to the beach, restaurants, and shopping. Can't wait to visit again!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Breezy Pad, Close to the Lake, with Hot Tub
Smart TV, DVD player, books

Breezy Pad, Close to the Lake, with Hot Tub

9.2 out of 10, Wonderful, (89)
"We had a great time and appreciated the little touches that made our stay great! "
The price is ￥35,119
￥44,573 total
includes taxes & fees
Aug 14 - Aug 15
Breezy Pad, Close to the Lake, with Hot Tub
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Fridge, microwave, oven, stovetop

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

10.0 out of 10, Exceptional, (56)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.
On the beach

Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

7.6 out of 10, Good, (22)
"Had a great time and enjoyed our stay "
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Outdoor pool, a heated pool

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

9.2 out of 10, Wonderful, (65)
"Had the best weekend at this house. The house was clean, updated, and had everything we could need. Will be staying again. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
3BR Condo Close To The Beach! In/OutDoor Pools
Interior

3BR Condo Close To The Beach! In/OutDoor Pools

10.0 out of 10, Exceptional, (96)
"Lovely condo in great location"
3BR Condo Close To The Beach! In/OutDoor Pools
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
TV, fireplace, books, stereo

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

8.6 out of 10, Excellent, (82)
"Great house, beautiful view, very clean"
The price is ￥37,470
￥91,009 total
includes taxes & fees
Aug 25 - Aug 26
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room
Outdoor dining

Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

10.0 out of 10, Exceptional, (209)
"We had a great stay; the layout was great for our family vacation."
Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Interior

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

9.8 out of 10, Exceptional, (140)
"Just perfect!! 4 levels. Plenty of back yard room and the beach was fantastic!!Everything was as stated in information!!Recommend to anybody. !!!"
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
Property grounds

7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

9.0 out of 10, Wonderful, (61)
"We had a fantastic time together."
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
Smart TV, fireplace, DVD player, printers

Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

9.4 out of 10, Exceptional, (100)
"Our family spent the holiday at this incredible house and everything was perfect. We would definitely stay here again and highly recommend it. "
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
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
Sign in
Sign up, it's free

Top Lakeside Hotel Reviews

Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

10/10 Excellent
"Good central spot for beach exploring"
Marcos 1-night trip
Posted 1 day ago
Quality Inn Near Interstate I94

Frequently asked questions

Are there vacation rentals in Lakeside?

Yes, you can find vacation rentals near popular attractions in Lakeside, or you can choose a secluded option if you're looking for relaxation. 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 vacation home rentals that Lakeside has to offer?

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants : This vacation home rental near Lakeside is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a terrace, and a garden so you can immerse yourself in your vacation.

How many vacation rentals will I find in Lakeside?

With 45 Expedia vacation rentals, you're sure 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 vacation rentals like in Lakeside?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Lakeside. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.