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, 185 reviews"The Pines" in Union Pier: Year-round getaway
Jun 16 – 23
Cottage in Michiana Shores
4.98 out of 5 average rating, 106 reviewsThe Pines Cottage on Birchwood
Oct 15 – 22
Cottage in Lakeside
4.98 out of 5 average rating, 138 reviews5 BR Lk Michigan Cottage for Family & Friends
Jan 2 – 9
Cottage in Union Pier
4.96 out of 5 average rating, 172 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
Nov 1 – 8
Cottage in Sawyer
4.94 out of 5 average rating, 185 reviewsBright Modern Designer Maple Street Beach House
Sep 30 – Oct 7
Cottage in Three Oaks
4.88 out of 5 average rating, 281 reviewsCottage with Character
Aug 29 – Sep 5
Cottage in Grand Beach
4.9 out of 5 average rating, 135 reviewsBeachglass Cottage - Family Friendly Kids and Pets
May 14 – 21
Cottage in Bridgman
4.79 out of 5 average rating, 154 reviewsCozy 1 BR & Loft Cottage: Lake Mich Dunes Wineries
May 6 – 13
Lakeside house rentals
Home in Union Pier
4.94 out of 5 average rating, 193 reviewsCASA TICA Serenity Amongst Nature Dog Friendly
Mar 30 – Apr 6
Home in Lakeside
4.94 out of 5 average rating, 144 reviewsAnnie's Attic, great place for friends and family
Sep 18 – 25
Home in Three Oaks
4.98 out of 5 average rating, 224 reviewsSycamore Cottage - Hot Tub - Steps to Downtown 2BR
Nov 12 – 19
Home in Union Pier
4.93 out of 5 average rating, 108 reviewsBarn & Beach - main house ( front)
Nov 29 – Dec 6
Home in Harbert
4.98 out of 5 average rating, 147 reviewsEntertain, Play & Relax in Harbert w/ Hot Tub
Nov 12 – 19
Home in Michigan City
4.94 out of 5 average rating, 414 reviewsSugar Babe Beach Retreat with Hot Tub!
Mar 12 – 19
Home in Michigan City
4.98 out of 5 average rating, 229 reviewsHouse of Zen: Peaceful Modern Cabin on Tryon Farm
Sep 3 – 10
Home in Three Oaks
4.99 out of 5 average rating, 111 reviewsDog Friendly Downtown Three Oaks Cottage! Fenced!
Mar 12 – 19
Lakeside fishing vacation rentals
Villa in Michigan City
4.9 out of 5 average rating, 127 reviewsSteps from the beach. Entire beach villa renovated
Feb 13 – 20
Cabin in Michiana
5.0 out of 5 average rating, 203 reviewsRomantic Getaway in the Dunes for a Couple—Hüüsli
Sep 10 – 17
Cabin in Michiana
4.97 out of 5 average rating, 111 reviewsSteps to the beach at luxury cabin 1hr to Chicago
Jan 5 – 12
Guesthouse in Berrien Springs
4.93 out of 5 average rating, 229 reviewsMake Lasting Memories at Beautiful Lake Chapin
Nov 25 – Dec 2
Apartment in Stevensville
4.91 out of 5 average rating, 699 reviewsQuiet Grand Mere Coach House on Lake Michigan
Nov 18 – 25
Home in Three Oaks
4.9 out of 5 average rating, 102 reviewsLuxe Life | Heated Pool | Hot Tub| Sleeps 10
Nov 10 – 17
Cottage in New Buffalo
4.99 out of 5 average rating, 206 reviewsThe Birdhouse – quiet luxury, walk everywhere
Sep 1 – 8
Apartment in La Porte
4.93 out of 5 average rating, 452 reviewsSecond Floor Apartment sitting on Pine Lake
Dec 10 – 17
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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