Lakeside house rentals
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Top-rated house rentals in Lakeside
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Popular amenities for Lakeside vacation rentals
Lakeside vacation rentals
Cabin in Union Pier
McComb's Cabin, Union Pier, MI
Guesthouse in New Buffalo
Rainbows End 🌈 Bourgeois
Guesthouse in Sawyer
Heron's Rest hideaway close to beaches, breweries
Cottage in Lakeside
Pebble Path Cottage - Less than a block to beach!
Farm stay in La Porte
Cabin on Swede Hill
Rental unit in Sawyer
Ozzie’s Hideaway-Smack between Three Oaks & Sawyer
Rental unit in Bridgman
Beachcomber Suite - Beaches, Dunes, Golf, Wine Tr
Farm stay in Sawyer
Your SW Michigan Modern Farmhouse Cottage Awaits
Lakeside cottage rentals
Cottage in Sawyer
Wishing Well Cottage
Cottage in Michiana Shores
The Pines Cottage on Birchwood
Cottage in Union Pier
Steps to the Beach! Screened in Porch & Firepit!
Cottage in Sawyer
Wine Country Cottage—walk to Lake Michigan/Dunes
Cottage in Union Pier
Union Pier Cottage—Steps to lake, hot tub, sauna!
Cottage in Three Oaks
Cottage with Character
Cottage in Sawyer
Northwind Llama retreat “Loft Cottage”
Cottage in Union Pier
J’s Beach House: Hot Tub & short walk to beach!
Lakeside fishing house rentals
Home in Rolling Prairie
Pure Michiana - Rustic & Cozy - near the stateline
Home in Michigan City
Midcentury marvel steps from beach! Pups
Home in Three Oaks
The Walnut House, Michigan Woods Retreat
Home in Michigan City
Charming Getaway House near Beach
Home in Three Oaks
Heated Pool IS OPEN!| Hot Tub| Sleeps 10
Home in Sawyer
Dunes Beach Retreat House
Home in Bremen
"SERENITY COTTAGE" Picturesque lake front w/3 bdr!
Home in New Buffalo
Debs 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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