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 Sawyer
4.93 out of 5 average rating, 210 reviewsNorthwind Llama retreat “Chicken coop”
Dec 9 – 16
Cottage in Three Oaks
4.88 out of 5 average rating, 281 reviewsCottage with Character
Sep 4 – 11
Cottage in Union Pier
4.97 out of 5 average rating, 186 reviews"The Pines" in Union Pier: Year-round getaway
Nov 12 – 19
Cottage in Union Pier
4.93 out of 5 average rating, 284 reviewsSteps to the Beach! Screened in Porch & Firepit!
Oct 26 – Nov 2
Cottage in Lakeside
4.98 out of 5 average rating, 138 reviews5 BR Lk Michigan Cottage for Family & Friends
Oct 17 – 24
Cottage in Union Pier
4.96 out of 5 average rating, 173 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
Nov 28 – Dec 5
Cottage in Sawyer
4.89 out of 5 average rating, 406 reviewsWine Country Cottage—walk to Lake Michigan/Dunes
Jan 15 – 22
Cottage in New Buffalo
4.93 out of 5 average rating, 322 reviewsTwin Cottage A- Walk to Beach & Town!
Feb 25 – Mar 4
Lakeside house rentals
Home in Lakeside
4.94 out of 5 average rating, 145 reviewsAnnie's Attic, great place for friends and family
Sep 3 – 10
Home in Three Oaks
4.98 out of 5 average rating, 225 reviewsSycamore Cottage - Hot Tub - Steps to Downtown 2BR
Nov 14 – 21
Home in Union Pier
4.93 out of 5 average rating, 112 reviewsBarn & Beach - main house ( front)
Feb 21 – 28
Home in Union Pier
4.94 out of 5 average rating, 193 reviewsCASA TICA Serenity Amongst Nature Dog Friendly
Oct 13 – 20
Home in Harbert
4.98 out of 5 average rating, 149 reviewsEntertain, Play & Relax in Harbert w/ Hot Tub
Dec 1 – 8
Home in Michigan City
4.94 out of 5 average rating, 414 reviewsSugar Babe Beach Retreat with Hot Tub!
Apr 4 – 11
Home in Sawyer
4.96 out of 5 average rating, 133 reviewsDarling Home + Hot Tub, Big Yard, by Warren Dunes
Nov 24 – Dec 1
Home in Three Oaks
4.98 out of 5 average rating, 106 reviewsCasa Gitana - Boutique Style Stay in Three Oaks
May 22 – 29
Lakeside fishing vacation rentals
Cabin in Michiana
5.0 out of 5 average rating, 203 reviewsRomantic Getaway in the Dunes for a Couple—Hüüsli
Oct 18 – 25
Cabin in Michiana
4.96 out of 5 average rating, 114 reviewsSteps to the beach at luxury cabin 1hr to Chicago
Feb 1 – 8
Apartment in Stevensville
4.91 out of 5 average rating, 702 reviewsQuiet Grand Mere Coach House on Lake Michigan
Sep 4 – 11
Villa in Michigan City
4.9 out of 5 average rating, 127 reviewsSteps from the beach. Entire beach villa renovated
Oct 26 – Nov 2
Guest suite in Decatur
4.98 out of 5 average rating, 257 reviewsRomantic Couples Lake Escape
Oct 12 – 19
Apartment in La Porte
4.93 out of 5 average rating, 452 reviewsSecond Floor Apartment sitting on Pine Lake
May 12 – 19
Cottage in Valparaiso
4.88 out of 5 average rating, 497 reviewsFlint Lake Cottage.
Sep 11 – 18
Home in Three Oaks
4.96 out of 5 average rating, 148 reviewsThe Walnut House, Michigan Woods Retreat
Nov 25 – Dec 2
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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