Lakeside house rentals
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Top-rated house rentals in Lakeside
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Other great vacation rentals in Lakeside
Cottage in Lakeside
4.99 out of 5 average rating, 101 reviewsPebble Path Cottage - Less than a block to beach!
Guesthouse in Sawyer
4.92 out of 5 average rating, 151 reviewsHeron's Rest hideaway close to beaches, breweries
Guesthouse in New Buffalo
4.99 out of 5 average rating, 274 reviewsRainbows End 🌈 Bourgeois
Cabin in Union Pier
4.96 out of 5 average rating, 293 reviewsMcComb's Cabin, Union Pier, MI
Farm stay in Sawyer
4.98 out of 5 average rating, 340 reviewsYour SW Michigan Modern Farmhouse Cottage Awaits
Guesthouse in New Buffalo
4.98 out of 5 average rating, 701 reviews"Tiny House" Guest House Under the Oak Trees
Cottage in Union Pier
4.98 out of 5 average rating, 150 reviewsUnion Pier Cottage—Steps to lake, hot tub, sauna!
Farm stay in La Porte
4.99 out of 5 average rating, 442 reviewsCabin on Swede Hill
Lakeside cottage rentals
Cottage in Sawyer
4.93 out of 5 average rating, 210 reviewsNorthwind Llama retreat “Chicken coop”
Cottage in Union Pier
4.93 out of 5 average rating, 285 reviewsSteps to the Beach! Screened in Porch & Firepit!
Cottage in Union Pier
4.97 out of 5 average rating, 186 reviews"The Pines" in Union Pier: Year-round getaway
Cottage in Lakeside
4.98 out of 5 average rating, 138 reviews5 BR Lk Michigan Cottage for Family & Friends
Cottage in Union Pier
4.96 out of 5 average rating, 173 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
Cottage in Three Oaks
4.88 out of 5 average rating, 281 reviewsCottage with Character
Cottage in Sawyer
4.89 out of 5 average rating, 406 reviewsWine Country Cottage—walk to Lake Michigan/Dunes
Cottage in Sawyer
4.94 out of 5 average rating, 185 reviewsBright Modern Designer Maple Street Beach House
Lakeside fishing house rentals
Home in Michigan City
4.97 out of 5 average rating, 232 reviewsHouse of Zen: Peaceful Modern Cabin on Tryon Farm
Home in Three Oaks
4.96 out of 5 average rating, 148 reviewsThe Walnut House, Michigan Woods Retreat
Home in Three Oaks
4.9 out of 5 average rating, 103 reviewsLuxe Life | Heated Pool | Hot Tub| Sleeps 10
Home in Benton Harbor
4.99 out of 5 average rating, 124 reviewsLake Michigan Panoramic View/Private Beach/Hot Tub
Home in Sawyer
4.93 out of 5 average rating, 125 reviewsDunes Beach Retreat House
Home in Michigan City
4.92 out of 5 average rating, 283 reviewsCharming Getaway House near Beach
Home in New Buffalo
4.92 out of 5 average rating, 141 reviewsThe Pump House Downtown New Buffalo
Home in New Buffalo
4.85 out of 5 average rating, 495 reviewsDebs Michigan hot tub house, open all year
Your guide to Lakeside
Introduction
Chicago residents have been escaping to the southeast coast of Lake Michigan for a century, and hidden among the tree-lined beaches of Lakeside are thousands of rustic cottages and inns. This is a retreat designed for relaxation: You can hike in the woods, swim, bike, go wine tasting, or just do nothing — many people are here specifically to soak up the sun and spend long afternoons reading amid the trees. Many shops, bars, and antique stores along Red Arrow Highway cater to urban tastes, and the mood is serene and friendly. (Lakeside is not an isolated getaway, however, and if you need to buy supplies, Michigan City, just over the Indiana border, is only 20 minutes away.)
The best time to stay in a vacation rental in Lakeside
If you prefer gentle climates, May through September are definitely the best months to visit the southern Lake Michigan coast. The lake tempers the heat during the summer, but temperatures in the 80s Fahrenheit are still common. As July segues into August the humidity goes up — you’ll want to make frequent trips to the lake to cool down. (Essential protections: sunglasses, sunblock, and bug spray.)
Autumn, which begins in mid-September, is a magnificent time to stay in one of the area’s cottage rentals, with crisp air and brilliantly colored foliage. Winters stretch from early December to the beginning of March. During those months, temperatures below the 40s Fahrenheit are the norm, and the lakeshore effect brings freezing winds and snows to much of southern Michigan and northern Indiana.
Top things to do in Lakeside
Warren Dunes State Park
Warren Dunes is kind of the Riviera of the southern coast, with miles of fine-sand beach that fills up with castle-builders and sun-seeking teenagers. If you hear excited screaming, look up to see kids who have climbed to the top of a 250-foot sand dune flying or rolling down.
Red Arrow Highway
This north-south road connects the towns of the southeastern Michigan coast, and the stretch from New Buffalo to Bridgeman is lined with galleries, craft stores, and antique shops selling both knickknacks and high-end furniture. You can also find welcoming cafes, roadhouses, and a beloved Turkish restaurant.
Three Oaks
The town of Three Oaks, just a few miles inland from Lakeside, is the center of the region’s biking culture. You can rent bikes from little cruisers to heavy-duty mountain bikes, and there’s a bike museum. Three Oaks has created 20 bike routes that range from short and flat to September’s Apple Cider Century bike tour of wine and orchard country.
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