Lakeside Vacation Rentals

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Our top choices for Lakeside vacation rentals

Secluded Country Cabin

Secluded Country Cabin
Berrien Springs
10.0 out of 10, Exceptional, (75 reviews)
"We had a great stay! We loved the privacy and the wedding gift the owners gave to us!"
United States
Savannah L.
$180 nightly
The price is $180
May 7 - May 8
Total with taxes and fees
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.
$428 nightly
The price is $479
May 7 - May 8
Total with taxes and fees
Treehouse Bungalow- Quaint and Cozy Getaway!

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, (19 reviews)
"The backyard/garage area was awesome! So much to do. The house was very clean and the beds were super comfortable! The host was also extremely response!"
United States
Franny
$564 nightly
The price is $571
May 12 - May 13
Total with taxes and fees
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!
Michigan City
8.8 out of 10, Excellent, (23 reviews)
"Good location great pool host was nice to deal with. Had a good time"
United States
T H.
$455 nightly
The price is $509
May 7 - May 8
Total with taxes and fees
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
$327 nightly
The price is $355
May 17 - May 18
Total with taxes and fees
Newly Renovated / Dog Friendly / Sleeps 6

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, (130 reviews)
"This place is so warm and cozy. Like walking back in time with the old kitchen appliances. Perfect for a winter getaway with a hot tub & amazing massage chair. The city is so beautiful to explore from Bennett’s Antique Store to Tavern on 12. Highly recommended will be booking again soon. Host was super responsive and respectful. "
United States
Jessi B.
$171 nightly
The price is $192
May 7 - May 8
Total with taxes and fees
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

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.
$218 nightly
The price is $229
May 7 - May 8
Total with taxes and fees
Romantic Cozy Home in "America’s Nicest Town"

Accessible Studio Suite w/ Kitchen & Breakfast

Accessible Studio Suite w/ Kitchen & Breakfast
Benton Harbor
$182 nightly
The price is $199
May 25 - May 26
Total with taxes and fees
Accessible Studio Suite w/ Kitchen & Breakfast

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, (31 reviews)
"Very nice place and all as advertised. Would stay here again"
United States
Murray
$408 nightly
The price is $416
May 12 - May 13
Total with taxes and fees
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
9.6 out of 10, Exceptional, (15 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.
$283 nightly
The price is $301
May 7 - May 8
Total with taxes and fees
The Boutique at Midtown Central / Hot Tub / Pet Friendly

Newely Remodeled Studio!

Newely Remodeled Studio!
Michigan City
9.0 out of 10, Wonderful, (16 reviews)
"It was amazing and close by the dunes for our National Park and hiking day. Nice area with lots of restaurants around, and the place was super clean and cozy!"
United States
JoC S.
$132 nightly
The price is $147
May 11 - May 12
Total with taxes and fees
Newely Remodeled Studio!

King Suite w/ Private Bedroom & Free Breakfast

King Suite w/ Private Bedroom & Free Breakfast
Benton Harbor
$153 nightly
The price is $168
May 10 - May 11
Total with taxes and fees
King Suite w/ Private Bedroom & Free Breakfast

Game room/ Hot Tub / Pet Friendly / Duplex

Game room/ Hot Tub / Pet Friendly / Duplex
Michigan City
10.0 out of 10, Exceptional, (5 reviews)
"The house was perfect for and we enjoyed the hot tub."
United States
Mistre S.
$300 nightly
The price is $321
May 7 - May 8
Total with taxes and fees
Game room/ Hot Tub / Pet Friendly / Duplex

Be Our -Country- Guest

Be Our -Country- Guest
New Carlisle
10.0 out of 10, Exceptional, (6 reviews)
"Great location!! "
United States
Kathy P.
$221 nightly
The price is $247
May 10 - May 11
Total with taxes and fees
Be Our -Country- Guest

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.
$349 nightly
The price is $367
May 7 - May 8
Total with taxes and fees
The 1888 House-Beach Town Luxury

No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Michigan City
9.8 out of 10, Exceptional, (25 reviews)
"We enjoyed the location and appreciated that the kitchen had the needed cookware for cooking!"
United States
Marijke W.
$223 nightly
The price is $250
May 10 - May 11
Total with taxes and fees
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

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.
$366 nightly
The price is $410
May 13 - May 14
Total with taxes and fees
Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center

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.
$364 nightly
The price is $407
May 7 - May 8
Total with taxes and fees
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

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.
$277 nightly
The price is $310
May 10 - May 11
Total with taxes and fees
Brand New Cottage Walkable to All Downtown Michigan City & Beach!

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, (173 reviews)
"Excellent location and lovely apartment! We loved our stay and will be back!!"
United States
Leslie C.
$269 nightly
The price is $283
May 18 - May 19
Total with taxes and fees
Stay in downtown Three Oaks overlooking the main street!
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lakeside vacation 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 low season months. For more hustle and bustle, you may prefer to visit Lakeside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $192 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Lakeside rentals

At Expedia, we put the best Lakeside vacation 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 vacation.

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 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?

Breezy Pad, Close to the Lake, with Hot Tub: This vacation home rental near Lakeside is located on a river and has a patio, a garden, and a barbecue grill 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 vacation with amenities like a selection of games.

How many vacation rentals will I find in Lakeside?

With 50 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.