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Top Holiday Rentals in Lakeside

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

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

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

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!

9.6 out of 10, Exceptional, (17)
"Loved the cottage it had everything we needed very nice!"
The price is £237
includes taxes & fees
3 Sept - 4 Sept
Walkable cozy cottage, Outlet Mall across street!

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

10.0 out of 10, Exceptional, (193)
"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.

9.4 out of 10, Exceptional, (116)
"It was quiet and clean and very enjoyable for me and my fiance! Will be going again!"
The price is £184
includes taxes & fees
2 Sept - 3 Sept
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

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 £337
includes taxes & fees
12 Aug - 13 Aug
Treehouse Bungalow- Quaint and Cozy Getaway!

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

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 £163
includes taxes & fees
7 Aug - 8 Aug
Breezy Pad, Close to the Lake, with Hot Tub

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.

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!

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

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

8.6 out of 10, Excellent, (82)
"Great house, beautiful view, very clean"
The price is £476
includes taxes & fees
25 Aug - 26 Aug
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

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

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!

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

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.
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Top Lakeside Hotel Reviews

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?

Breezy Pad, Close to the Lake, with Hot Tub: This holiday home rental outside of Lakeside is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.