Lakeside vacation rentals
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Top-rated vacation rentals in Lakeside
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Other great vacation rentals in Lakeside
Cottage in Union Pier
4.97 out of 5 average rating, 184 reviews"The Pines" in Union Pier: Year-round getaway
Sep 25 – Oct 2
Cottage in Three Oaks
4.88 out of 5 average rating, 281 reviewsCottage with Character
Sep 18 – 25
Cottage in Union Pier
4.96 out of 5 average rating, 172 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
Nov 20 – 27
Cottage in Union Pier
4.81 out of 5 average rating, 205 reviewsThe Koi Cottage - Union Pier- Dog Friendly!
Oct 18 – 25
Cottage in Grand Beach
4.9 out of 5 average rating, 134 reviewsBeachglass Cottage - Family Friendly Kids and Pets
Dec 7 – 14
Cottage in Sawyer
4.94 out of 5 average rating, 185 reviewsBright Modern Designer Maple Street Beach House
Oct 23 – 30
Cottage in Michiana Shores
4.98 out of 5 average rating, 106 reviewsThe Pines Cottage on Birchwood
Sep 14 – 21
Cottage in Three Oaks
4.9 out of 5 average rating, 105 reviewsPrivate, Sun-filled Union Pier Cottage
Mar 18 – 25
Lakeside house rentals
Home in Union Pier
4.92 out of 5 average rating, 106 reviewsBarn & Beach - main house ( front)
Oct 24 – 31
Home in Harbert
4.98 out of 5 average rating, 146 reviewsEntertain, Play & Relax in Harbert w/ Hot Tub
Nov 22 – 29
Home in Sawyer
4.92 out of 5 average rating, 298 reviewsCozy Mid-Century Mod By Lake MI&Dunes with Hot Tub
Jan 5 – 12
Home in Michigan City
4.89 out of 5 average rating, 442 reviewsBeautiful beach bungalow with hiking and hot tub!
Mar 25 – Apr 1
Home in Sawyer
4.96 out of 5 average rating, 132 reviewsDarling Home + Hot Tub, Big Yard, by Warren Dunes
Aug 16 – 23
Home in Three Oaks
4.98 out of 5 average rating, 224 reviewsSycamore Cottage - Hot Tub - Steps to Downtown 2BR
Feb 19 – 26
Home in Union Pier
4.94 out of 5 average rating, 193 reviewsCASA TICA Serenity Amongst Nature Dog Friendly
Jan 2 – 9
Home in La Porte
4.94 out of 5 average rating, 208 reviewsCamp Knotty Pine
May 31 – Jun 7
Lakeside fishing vacation rentals
Cabin in Michiana
5.0 out of 5 average rating, 202 reviewsRomantic Getaway in the Dunes for a Couple—Hüüsli
Oct 1 – 8
Cabin in Michiana
4.97 out of 5 average rating, 110 reviewsSteps to the beach at luxury cabin 1hr to Chicago
Dec 9 – 16
Tiny home in Sawyer
4.8 out of 5 average rating, 122 reviewsAfter Dune Delight
Oct 9 – 16
Villa in Michigan City
4.9 out of 5 average rating, 127 reviewsSteps from the beach. Entire beach villa renovated
Oct 18 – 25
Apartment in Stevensville
4.91 out of 5 average rating, 699 reviewsQuiet Grand Mere Coach House on Lake Michigan
Oct 22 – 29
Guesthouse in Berrien Springs
4.93 out of 5 average rating, 229 reviewsMake Lasting Memories at Beautiful Lake Chapin
Sep 11 – 18
Home in Three Oaks
4.96 out of 5 average rating, 146 reviewsThe Walnut House, Michigan Woods Retreat
Jun 13 – 20
Home in Rolling Prairie
4.96 out of 5 average rating, 173 reviewsRustic Elegance in the Michiana area
Aug 15 – 22
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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