Lakeside Vacation Rentals

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Our top choices for Lakeside vacation rentals

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

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Michigan City
9.4 out of 10, Exceptional, (126)
"Was as described great stay"
United States
Amber C.
$179 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

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, (19)
"Great stay, loved the place!"
United States
Ryan J.
$329 nightly
The price is $334
Dec 15 - Dec 16
Total with taxes and fees
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach

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)
"It was a lovely stay! Very clean and it was awesome I could take my dog with me :)"
United States
Roxie
$281 nightly
The price is $286
Dec 15 - Dec 16
Total with taxes and fees
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Breezy Pad, Close to the Lake, with Hot Tub

Breezy Pad, Close to the Lake, with Hot Tub
St Joseph
9.2 out of 10, Wonderful, (106)
"We stayed at the Breezy pad for a family vacation and it was wonderful. We were able to bring our dog with and the house was very dog and family friendly. We loved that it was close to plenty of beaches and the neighborhood was very family friendly and quiet. We will definitely be making this a yearly family vacation. "
United States
Anna E.
$155 nightly
The price is $162
Dec 11 - Dec 12
Total with taxes and fees
Breezy Pad, Close to the Lake, with Hot Tub

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)
"Cozy house close to New Buffalo. Yard was great and game room was great additional space to hang out in. Would definitely go back!"
United States
Liz W.
$300 nightly
The price is $305
Dec 11 - Dec 12
Total with taxes and fees
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

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, (33)
"Nice"
United States
Maryellen W.
$319 nightly
The price is $357
Dec 14 - Dec 15
Total with taxes and fees
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Equipped Studio | Free Daily Breakfast, Indoor Pool + Fitness Center

Equipped Studio | Free Daily Breakfast, Indoor Pool + Fitness Center
2.0 star property
Benton Harbor
10.0 out of 10, Exceptional, (1)
"Very clean, nice breakfast. No hot tub and remote for tv didnt work. Otherwise good. Amazingly clean. "
United States
Amanda M.
$121 nightly
The price is $132
Jan 2 - Jan 3, 2026
Total with taxes and fees
Equipped Studio | Free Daily Breakfast, Indoor Pool + Fitness Center

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, (18)
"Loved our stay! Was a great landing spot for us while we were out exploring Indiana Dunes with our pups. Close to everything we needed, including the winery we treated ourselves to during our stay!"
United States
Katelyn S.
$159 nightly
The price is $178
Dec 11 - Dec 12
Total with taxes and fees
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

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)
"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.
$216 nightly
The price is $230
Dec 11 - Dec 12
Total with taxes and fees
Heart of Historical Dist.*Parking*Claw Tub*A/C #4

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)
"It was very cozy and perfect! "
United States
Tommy W.
$145 nightly
The price is $162
Dec 18 - Dec 19
Total with taxes and fees
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown

Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown
New Buffalo
9.6 out of 10, Exceptional, (5)
"Fun spot, close to many activities to enjoy."
United States
Jody W.
$452 nightly
The price is $457
Dec 14 - Dec 15
Total with taxes and fees
Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown

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

Grand Reunion House 1 / Hot Tub / Pet Friendly / Duplex
2.0 star property
Michigan City
9.8 out of 10, Exceptional, (7)
"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.
$257 nightly
The price is $273
Dec 11 - Dec 12
Total with taxes and fees
Grand Reunion House 1 / Hot Tub / Pet Friendly / Duplex

The Loft Buchanan - Chic Industrial Loft in Historic Downtown

The Loft Buchanan - Chic Industrial Loft in Historic Downtown
Buchanan
10.0 out of 10, Exceptional, (4)
"The property was extremely clean and perfectly described. Very cute inside. It was the perfect size for our group of 4 women. The loft was fine for us but might be difficult for some people to access. "
United States
Kelly D.
$245 nightly
The price is $253
Dec 11 - Dec 12
Total with taxes and fees
The Loft Buchanan - Chic Industrial Loft in Historic Downtown

Romantic Cozy Home in "America’s Nicest Town"

Romantic Cozy Home in "America’s Nicest Town"
Buchanan
9.8 out of 10, Exceptional, (14)
"Was the perfect location for our trip to Niles/Buchanan area "
United States
Kathy J.
$195 nightly
The price is $205
Dec 11 - Dec 12
Total with taxes and fees
Romantic Cozy Home in "America’s Nicest Town"

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)
"Home very well stocked, very cute and clean inside. We're able to walk to restaurants and Sheridan beaches. Very friendly and safe area. Wine tasting, golfing and excellent restaurants nearby."
United States
Marie H.
$191 nightly
The price is $202
Dec 11 - Dec 12
Total with taxes and fees
Duplex | Firepit | Game Room | Hot Tub-all year

Beachfront Hot Tub All Year | Outdoor Grill | Waves on Lake Michigan

Beachfront Hot Tub All Year | Outdoor Grill | Waves on Lake Michigan
Michigan City
10.0 out of 10, Exceptional, (1)
"We had a great trip. Location with direct access to the beach was a must for us and this home did not disappoint. Plenty of room for all of us. It was our kids and a few of their friends. Loved that we had space to spread out. The kids had the downstairs and we could relax upstairs. House was clean. Kitchen was well stocked. Beds were super comfortable. Plenty of parking. The screened in porch was a great place for morning coffee and evening wine."
United States
Brook W.
$490 nightly
The price is $513
Dec 11 - Dec 12
Total with taxes and fees
Beachfront Hot Tub All Year | Outdoor Grill | Waves on Lake Michigan

Secluded Country Cabin

Secluded Country Cabin
Berrien Springs
10.0 out of 10, Exceptional, (74)
"We thoroughly enjoyed our stay. Charming, family-friendly and with gracious hosts. Check-in and check-our was a breeze. Thank you!"
United States
Joshua J.
$181 nightly
The price is $189
Dec 11 - Dec 12
Total with taxes and fees
Secluded Country Cabin

5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022

5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022
Michigan City
8.0 out of 10, Very Good, (2)
"It was very close to the casino peaceful "
United States
darnell
$388 nightly
The price is $435
Dec 11 - Dec 12
Total with taxes and fees
5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022

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, (10)
"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.
$279 nightly
The price is $297
Dec 11 - Dec 12
Total with taxes and fees
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)
"Beautiful and feels like home! Great location too! "
United States
Michelle T.
$263 nightly
The price is $295
Dec 11 - Dec 12
Total with taxes and fees
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
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 $200 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?

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.: This vacation home rental near Lakeside offers a balcony, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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.