Holiday Rentals in Lakeside

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Our top choices for Lakeside holiday rentals

Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
New Buffalo
10.0 out of 10, Exceptional, (16 reviews)
"Great cozy place with great yard and activity space"
United States
Derek E.
The price is €338
includes taxes & fees
3 Mar - 4 Mar
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Michigan City
9.6 out of 10, Exceptional, (49 reviews)
"It was a wonderful stay. The house is cozy and spacious in a wonderful neighborhood. It was very peaceful. "
United States
B E.
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach
Michigan City
10.0 out of 10, Exceptional, (1 review)
"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 €225
includes taxes & fees
5 Feb - 6 Feb
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Michigan City
9.4 out of 10, Exceptional, (34 reviews)
"Enjoyed our stay. Lots of room, easy to find, close to Lake Michigan, and received clear and helpful communication from the property manager/owner before and during our stay. "
United States
Daniel A.
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Scenic Southwest Michigan Awaits!

Scenic Southwest Michigan Awaits!
Baroda
10.0 out of 10, Exceptional, (134 reviews)
"Amazing location, beautiful home, clean, quiet neighborhood. Very happy with the stay will definitively be going back! "
United States
Kyle C.
The price is €159
includes taxes & fees
5 Feb - 6 Feb
Scenic Southwest Michigan Awaits!

The Boutique at Midtown Central / Hot Tub / Pet Friendly

The Boutique at Midtown Central / Hot Tub / Pet Friendly
Michigan City
9.8 out of 10, Exceptional, (11 reviews)
"We loved staying here. Jason was a great communicator and made sure our needs were met. Plenty of beds for our family of 8 adults. 10 minutes to the national park and its pristine beaches. "
United States
Cindy W.
The price is €257
includes taxes & fees
5 Feb - 6 Feb
The Boutique at Midtown Central / Hot Tub / Pet Friendly

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

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Michigan City
9.2 out of 10, Wonderful, (127 reviews)
"Hot tub was great! "
United States
Caitlin R.
The price is €237
includes taxes & fees
3 Mar - 4 Mar
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Brand New Cottage Walkable to All Downtown Michigan City & Beach!

Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Michigan City
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and feels like home! Great location too! "
United States
Michelle T.
The price is €264
includes taxes & fees
5 Feb - 6 Feb
Brand New Cottage Walkable to All Downtown Michigan City & Beach!

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (29 reviews)
"Highly recommend very clean, beautiful kitchen my family enjoyed staying there and my dog enjoyed the fenced in backyard"
United States
Mary B.
The price is €385
includes taxes & fees
3 Mar - 4 Mar
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Grand Reunion House 1 / Hot Tub / Pet Friendly / Duplex

Grand Reunion House 1 / Hot Tub / Pet Friendly / Duplex
Michigan City
9.8 out of 10, Exceptional, (7 reviews)
"We had a great stay! Jason was quick to respond to any messages and sent us detailed communications leading up to our stay. Space was perfect for me, my husband, and our two dogs. Location is super close to the beach, casino, and outlet shopping. Would for sure recommend!"
United States
Missy S.
The price is €239
includes taxes & fees
5 Feb - 6 Feb
Grand Reunion House 1 / Hot Tub / Pet Friendly / Duplex

Heart of Historical Dist.*Parking*Claw Tub*A/C #4

Heart of Historical Dist.*Parking*Claw Tub*A/C #4
Michigan City
10.0 out of 10, Exceptional, (7 reviews)
"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 €199
includes taxes & fees
5 Feb - 6 Feb
Heart of Historical Dist.*Parking*Claw Tub*A/C #4

Singing Sands Trl | Hot Tub Retreat | Dogs OK

Singing Sands Trl | Hot Tub Retreat | Dogs OK
Michigan City
9.8 out of 10, Exceptional, (25 reviews)
"I absolutely loved it there the beds were comfy the hot tub was nice we enjoyed a fire and we got a chance to relax and catch up very great birthday thanks a lot "
United States
Britni S.
The price is €205
includes taxes & fees
5 Feb - 6 Feb
Singing Sands Trl | Hot Tub Retreat | Dogs OK

Romantic Cozy Home in "America’s Nicest Town"

Romantic Cozy Home in "America’s Nicest Town"
Buchanan
9.8 out of 10, Exceptional, (15 reviews)
"Was the perfect location for our trip to Niles/Buchanan area "
United States
Kathy J.
Romantic Cozy Home in "America’s Nicest Town"

Secluded Country Cabin

Secluded Country Cabin
Berrien Springs
10.0 out of 10, Exceptional, (74 reviews)
"Awesome people and a awesome place to stay we have been there 4 times and just love it and love the owners......Thank you for this place God bless you "
United States
Kevin & Susan O.
The price is €164
includes taxes & fees
8 Feb - 9 Feb
Secluded Country Cabin

3 Bed 3 Ba Screenporch/Sunset Lake Views

3 Bed 3 Ba Screenporch/Sunset Lake Views
LaPorte, Indiana, US
10.0 out of 10, Exceptional, (68 reviews)
"Gorgeous fall break get-away! Minutes into town for Mama T's breakfast or Enzo's for dinner. Quiet lake view setting with running/biking trails. Easy 35 minute drive into South Bend for a Notre Dame game. Lots of space for our 3 teenage boys to spread out. 10/10 recommend!"
United States
Erin H.
3 Bed 3 Ba Screenporch/Sunset Lake Views

Duplex | Firepit | Game Room | Hot Tub-all year

Duplex | Firepit | Game Room | Hot Tub-all year
Michigan City
8.6 out of 10, Excellent, (17 reviews)
"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 €176
includes taxes & fees
5 Feb - 6 Feb
Duplex | Firepit | Game Room | Hot Tub-all year

Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Michigan City
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful overnight stay! Comfy house with clean amenities. Great experience! "
United States
Leah K.
The price is €202
includes taxes & fees
8 Feb - 9 Feb
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

Stay in downtown Three Oaks overlooking the main street!

Stay in downtown Three Oaks overlooking the main street!
Three Oaks
9.8 out of 10, Exceptional, (162 reviews)
"Had a nice stay, in this nice, clean and spacious Vrbo. "
United States
Matthew W.
The price is €235
includes taxes & fees
8 Feb - 9 Feb
Stay in downtown Three Oaks overlooking the main street!

Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach

Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (20 reviews)
"Great stay, loved the place!"
United States
Ryan J.
The price is €349
includes taxes & fees
5 Feb - 6 Feb
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach

Indoor Pool & Gym. Free Breakfast Buffet Included!

Indoor Pool & Gym. Free Breakfast Buffet Included!
Benton Harbor
Indoor Pool & Gym. Free Breakfast Buffet Included!
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, apart-hotels, 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 €167 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?

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!: This highly rated holiday home rental in Lakeside is located on a lake, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Lakeside?

With 46 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.