
Cottage vacation rentals in Lakeside
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Top-rated cottage rentals in Lakeside
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Lakeside cottage rentals
Lakefront cottage rentals

Lake Shore Cottage at Stone Lake-Serenity

Barron Lake front Cottage. Notre Dame Nearby!

Stylish Lakehouse, Sandy Beach Includes lux Boat!

Lakeside Getaway

Lakefront A-Frame - Beach, Kayaks & Pontoon Rental

Channel House on Indian Lake

Lake House 11 miles from Notre Dame

Private Vandalia Beach Front Cottage
Cottage rentals with a hot tub

Cozy Cottage Steps to Beach, Pool, Hot Tub & More

Charming Cottage - Hot Tub, Sauna, Large Yard

Casa Playa New House in Union Pier w/ Private Spa

Cottage near Hagar Beach Pet friendly with Hot tub

Hot tub! Red Tin Cottage of Harbor Country!

J’s Beach House: Hot Tub & short walk to beach!

Blueberry Fields/ House and Retreat

Hot tub open year round in modern/rustic cottage!
Pet-friendly cottage rentals

Northwind Llama retreat 'Loft Cottage'

New Buffalo retreat - Perfect year-round getaway!

"The Pines" in Union Pier: Year-round getaway

DKM Cottage - 15 minute walk to Lake Michigan

The Happy Cozy-Pets Welcome, Fire Pit, Privacy

Camp Wanderlust-Cozy lodge-20 minute walk to beach

Twin Cottage A- Walk to Beach & Town!

Cottage with Character
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- Millennium Park
- Navy Pier
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- University of Notre Dame
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Potato Creek State Park
- Willis Tower
- Lincoln Park
- Chicago Cultural Center
- Silver Beach Carousel
- Promontory Point
- Washington Park Zoo
- Point O' Woods Golf & Country Club
- Skydeck Chicago
- Deep River Waterpark
- South Bend Country Club
- Maggie Daley Park
- Museum of Contemporary Art Chicago
- Family travel hub Tips and inspiration
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- Kid-friendly state parks Check out these family-friendly hikes