Lakeside Vacation Rentals

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Our top choices for Lakeside vacation rentals

Indoor Pool & Gym. Free Breakfast Buffet Included!

Indoor Pool & Gym. Free Breakfast Buffet Included!
Benton Harbor
The price is CA $164
CA $209 total
includes taxes & fees
Mar 29 - Mar 30
Indoor Pool & Gym. Free Breakfast Buffet Included!

Secluded Country Cabin

Secluded Country Cabin
Berrien Springs
10.0 out of 10, Exceptional, (74 reviews)
"We had a great stay! We loved the privacy and the wedding gift the owners gave to us!"
United States
Savannah L.
The price is CA $192
CA $260 total
includes taxes & fees
Mar 25 - Mar 26
Secluded Country Cabin

Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (55 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is CA $246
CA $655 total
includes taxes & fees
Apr 1 - Apr 2
Treehouse Bungalow- Quaint and Cozy Getaway!

Saint Joe & Stevensville Shenanigans

Saint Joe & Stevensville Shenanigans
St. Joseph
10.0 out of 10, Exceptional, (51 reviews)
"Great stay, clean house, clean property. Had everything provided for us that we could have neeeded."
United States
Justin G.
The price is CA $177
CA $485 total
includes taxes & fees
Mar 25 - Mar 26
Saint Joe & Stevensville Shenanigans

Romantic Cozy Home in "America’s Nicest Town"

Romantic Cozy Home in "America’s Nicest Town"
Buchanan
9.8 out of 10, Exceptional, (16 reviews)
"Was the perfect location for our trip to Niles/Buchanan area "
United States
Kathy J.
The price is CA $159
CA $312 total
includes taxes & fees
Mar 25 - Mar 26
Romantic Cozy Home in "America’s Nicest Town"

Breezy Pad, Close to the Lake, with Hot Tub

Breezy Pad, Close to the Lake, with Hot Tub
St Joseph
9.0 out of 10, Wonderful, (116 reviews)
"Loved the quiet surroundings, yet being close to shopping and restaurants as well as the lake. "
United States
Jess B.
The price is CA $191
CA $271 total
includes taxes & fees
Mar 29 - Mar 30
Breezy Pad, Close to the Lake, with Hot Tub

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, (167 reviews)
"Excellent location and lovely apartment! We loved our stay and will be back!!"
United States
Leslie C.
The price is CA $185
CA $387 total
includes taxes & fees
Mar 25 - Mar 26
Stay in downtown Three Oaks overlooking the main street!

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.
The price is CA $119
CA $529 total
includes taxes & fees
Mar 25 - Mar 26
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

1 Bedroom | Free Daily Breakfast, Indoor Pool

1 Bedroom | Free Daily Breakfast, Indoor Pool
Benton Harbor
The price is CA $183
CA $230 total
includes taxes & fees
Mar 31 - Apr 1
1 Bedroom | Free Daily Breakfast, Indoor Pool

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

Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
New Buffalo
9.8 out of 10, Exceptional, (17 reviews)
"Great cozy place with great yard and activity space"
United States
Derek E.
The price is CA $157
CA $773 total
includes taxes & fees
Mar 30 - Mar 31
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

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, (30 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 CA $178
CA $565 total
includes taxes & fees
Mar 30 - Mar 31
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

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, (12 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 CA $167
CA $411 total
includes taxes & fees
Mar 25 - Mar 26
The Boutique at Midtown Central / Hot Tub / Pet Friendly

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)
"Cute place, extremely clean, comfortable and well-outfitted. It's very convenient, with easy parking and great proximity to downtown Michigan City. "
United States
Heather O.
The price is CA $161
CA $421 total
includes taxes & fees
Mar 26 - Mar 27
Brand New Cottage Walkable to All Downtown Michigan City & Beach!

The 1888 House-Beach Town Luxury

The 1888 House-Beach Town Luxury
Benton Harbor
9.4 out of 10, Exceptional, (9 reviews)
"We had a great weekend. Place was clean and host was very quick to respond."
United States
Abel H.
The price is CA $283
CA $501 total
includes taxes & fees
Mar 29 - Mar 30
The 1888 House-Beach Town Luxury

Scenic Southwest Michigan Awaits!

Scenic Southwest Michigan Awaits!
Baroda
10.0 out of 10, Exceptional, (135 reviews)
"Perfect home for a small family. Love that it had 2 bathrooms."
United States
April S.
The price is CA $154
CA $294 total
includes taxes & fees
Mar 31 - Apr 1
Scenic Southwest Michigan Awaits!

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK
Michigan City
9.8 out of 10, Exceptional, (40 reviews)
"We had a great stay. The house was warm, cozy and quiet. We were close to everything we wanted. "
United States
Jerilyn M.
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center

Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
New Carlisle
9.6 out of 10, Exceptional, (25 reviews)
"Everything matched the description. Jacqueline was an excellent host and we highly recommend her along with this property!"
United States
Tim S.
The price is CA $302
CA $559 total
includes taxes & fees
Apr 4 - Apr 5
Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center

UncleLarry's LakePlace, Hot Tub

UncleLarry's LakePlace, Hot Tub
La Porte
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful lake house stay, very refreshing! Lovely views of the lake and quiet area when we were there in November. Super comfy beds, great hot tub, and amazing view. Would definitely stay here again!"
United States
Jessica E.
The price is CA $315
CA $801 total
includes taxes & fees
Mar 29 - Mar 30
UncleLarry's LakePlace, Hot Tub

Brand New House with Hot Tub! Gameroom! Workspace!

Brand New House with Hot Tub! Gameroom! Workspace!
Michigan City
9.4 out of 10, Exceptional, (6 reviews)
"Check in was very easy and convenient. Kitchen was stocked with everything we needed. We will definitely stay here again."
United States
Donna M.
The price is CA $230
CA $556 total
includes taxes & fees
Mar 25 - Mar 26
Brand New House with Hot Tub! Gameroom! Workspace!

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, (129 reviews)
"Hot tub was great! "
United States
Caitlin R.
The price is CA $144
CA $323 total
includes taxes & fees
Mar 26 - Mar 27
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lakeside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!: This Lakeside vacation home rental is located on a lake and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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.