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Popular Lakeside Vacation Rentals

Find the perfect Lakeside vacation rental

House Lakeside
from $556 per night
House ∙ 8 guests ∙ 3 bedrooms

138 m² House

4.2
Very good(25 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
House Lakeside
-15%
$656
from $491 per night
House ∙ 8 guests ∙ 3 bedrooms

138 m² House

4.2
Very good(25 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vacasa
Details
Lodge Lakeside
from $1,343 per night
Lodge ∙ 25 guests ∙ 13 bedrooms

836 m² Lodge

4.9
Outstanding(107 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
House Lakeside
from $1,113 per night
20 guests ∙ 7 bedrooms

House

5.0
Outstanding(57 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
Cottage Lakeside
from $177 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

116 m² Cottage

4.0
Very good
Lakeside, Chikaming Township, Michigan, United States
Vacasa
Details
House Lakeside
from $325 per night
16 guests ∙ 6 bedrooms

House

4.9
Outstanding(24 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
House Lakeside
from $902 per night
House ∙ 16 guests ∙ 6 bedrooms

279 m² House

5.0
Outstanding(104 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
Cottage Lakeside
from $354 per night
Cottage ∙ 20 guests ∙ 9 bedrooms

325 m² Cottage

4.6
Excellent(67 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
Farmhouse Lakeside
from $860 per night
Farmhouse ∙ 14 guests ∙ 7 bedrooms

390 m² Farmhouse

5.0
Outstanding(69 ratings)
Lakeside, Chikaming Township, Michigan, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Lakeside
from $176 per night
House ∙ 9 guests ∙ 4 bedrooms

153 m² House

4.8
Outstanding(29 ratings)
Lakeside, Chikaming Township, Michigan, United States
Pool
Vacasa
Details
House  Lakeside
from $2,477 per night
House ∙ 18 guests ∙ 6 bedrooms

452 m² House

4.9
Outstanding(22 ratings)
Lakeside, Chikaming Township, Michigan, United States
Pool
Vacasa
Details
House  Lakeside
from $1,139 per night
House ∙ 16 guests ∙ 8 bedrooms

418 m² House

4.9
Outstanding(30 ratings)
Lakeside, Chikaming Township, Michigan, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

Cottage  Lakeside
from $489 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

232 m² Cottage

5.0
Outstanding(18 ratings)
Lakeside, Chikaming Township, Michigan, United States
Pet-friendly
Vrbo
Details
Cottage  Lakeside
from $215 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

96 m² Cottage

4.7
Excellent(40 ratings)
Lakeside, Chikaming Township, Michigan, United States
Pet-friendly
Vrbo
Details
House  Lakeside
from $351 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(8 ratings)
Lakeside, Chikaming Township, Michigan, United States
Pet-friendly
Vrbo
Details
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Vacation rentals with a balcony

House  Lakeside
from $407 per night
House ∙ 12 guests ∙ 4 bedrooms

250 m² House

5.0
Outstanding(26 ratings)
Lakeside, Chikaming Township, Michigan, United States
Balcony
HomeToGo
Details
House  Lakeside
from $843 per night
House ∙ 14 guests ∙ 5 bedrooms

546 m² House

5.0
Outstanding(4 ratings)
Lakeside, Chikaming Township, Michigan, United States
Balcony
Vacasa
Details
House  Lakeside
from $517 per night
House ∙ 10 guests ∙ 4 bedrooms

261 m² House

5.0
Outstanding(23 ratings)
Lakeside, Chikaming Township, Michigan, United States
Balcony
Vrbo
Details
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Frequently Asked Questions

What is the average price per night for accommodation in Lakeside?

Vacation rentals in Lakeside are priced starting at $158 per night.

Is it possible to find vacation rentals in Lakeside?

Tripping.com offers great selection on vacation rentals with 789 offers currently available in Lakeside.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Lakeside Information

About Lakeside

Located on the shores of Lake Michigan, the town of Lakeside in Berrien Country is part of what is known as Harbor Country, a small area with eight charming towns of Lakeside, New Buffalo, Union Pier, Harbert, Warren Dunes, Sawyer, Three Oaks, and Michiana. Lakeside is known for its lovely scenery and rustic lifestyle, which provide great reasons for a weekend getaway. Lakeside is located in the southwest corner of Michigan and is very close to Chicago. This has made Lakeside a popular destination for Chicago residents since the 1920s. True to its name, Lakeside sits on the shores of Lake Michigan, with slightly warmer weather than Chicago. Visitors can drive to freshwater beaches to build sandcastles or go swimming.

Things to do in Lakeside

If you’re visiting Lakeside in the warmer months of the year, go to the beach! You’ll have a lovely time sitting in the warm sand relaxing or reading, and cooling off with a swim in the lake. Walk around the town center to see the coffee shops and boutiques, or to treat yourself to some ice cream in the afternoon. Visitors can also take a boat out on the water (weather permitting) and spend the afternoon sailing. If you are interested in exploring the shoreline or are looking for more of an active day, go kayaking along the lake or in one of the nearby rivers. Even in lower temperatures, a walk along the sandy dunes is always a pleasant and relaxing time. Avid golfers should check out the Chikaming Country Club, a well-maintained 18-hole course that has been open since 1913 and is currently managed by John Phillips, PGA. Once you have played through Chikaming, explore Whittaker Woods Golf Club or Grand Beach Golf Course just a couple of miles south.

Day Trips From Lakeside

For a nearby day trip, tourists have the opportunity to visit the 1,950-acre Warren Dunes State Park. The park is open throughout the entire year and has numerous small paths for walking (bikes are not permitted). In addition to the usual beachside activities, visitors have the freedom to choose to hang-glide in the park, where sand dunes can be as tall as 240 feet. Finally, visitors can also explore any of the other eight towns of Harbor Country, all of which are along a fifteen-mile stretch on the shores of Lake Michigan. Each town is quaint and full of rustic charm, and most of them are tiny enough for the visitors to see within one day.

Lakeside Accommodations

Lakeside has many different accommodation options including cottages and vacation rentals that make for the perfect big city getaway. Most of these accommodations include top notch amenities such as a hot tub, fireplace, and hammocks. Visitors can also opt for bed and breakfast establishments, inns, and small hotels. Try to stay as close to the lake as possible so that you can watch the magnificent sunset.

Transportation In Lakeside

Visitors to Lakeside will need to bring their own car or rent one from the nearest rental service. Alternatively, biking is a great way to explore the green countryside of Lakeside and Harbor Country. A backroads bikeway system of 20 paved bike trails offers cyclists the option to go on self-guided tours ranging from 5 to 60 miles.

Popular Day Trips Near Lakeside

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