
Vacation rentals in Lakeside
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Top-rated vacation rentals in Lakeside
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Popular amenities for Lakeside vacation rentals
Lakeside fishing vacation rentals

Steps to Beach & Starbucks! Private Yard, Firepit!

The Pines Cottage on Birchwood

Cozy Green Cottage with Private Beach

Pet friendly, lakefront home directly on Pine Lake

The Walnut House, Michigan Woods Retreat

Designer Cottage Relax Pool Beach & Spa—Windjammer

House of Zen: Peaceful Modern Cabin on Tryon Farm

Superhost, hot tub, golf cart, fire pit, large!
Lake side house rentals in Lakeside

Splash (Pool! Hot Tub!) at Aqua House by the Lake

Lake House Retreat with a Pool

Arcade/Game Room • Private Beach Access • Fire Pit

Three Oaks Creek House Perfect

Lake Michigan•Private Beach•Amazing View•Hot Tub

Hot tub! In the heart of Three Oaks!

Pure Michiana - Rustic & Cozy - near the stateline

Beach! Hot Tub! New Buffalo! Firepit! King Bed!
Lakeside fishing house rentals

Lakefront 4BR w/private beach & panoramic views

The Luna Cottages - Unit 3 - Private Beach Access!

Land & Lake Getaway!

Renovated 3BR Lakefront | Balcony | Firepit | W/D

Private Island-Foot bridge to island-Sister Lakes-

Private! Cherry Beach Pool House

Sunrise Cottage on Clear Lake!

Updated-Private Beach-Lake Views-Hot Tub-Fire Pit
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.
Destinations to explore
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- Lincoln Park
- Millennium Park
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Oak Street Beach
- Warren Dunes State Park
- The Field Museum
- University of Notre Dame
- Washington Park Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Silver Beach Carousel
- Potato Creek State Park
- Chicago Cultural Center
- Deep River Waterpark
- Adler Planetarium
- DuSable Museum of African American History
- Chicago History Museum
- Woodlands Course at Whittaker
- The Dunes Club
- Buckingham Fountain
- Family travel hub Tips and inspiration
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