
Holiday rentals in Lakeside
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Top-rated holiday rentals in Lakeside
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Lakeside holiday rentals
Other great holiday rentals in Lakeside

Home in Lakeside
4.6 out of 5 average rating, 10 reviews2BR garden-style cottage with beach access

Home in Three Oaks
5 out of 5 average rating, 3 reviewsJust Updated in Lakeside | Pool + Hot Tub + Porch!
Superhost

Home in Lakeside
4.67 out of 5 average rating, 21 reviewsRenovated 3BR Lakefront | Balcony | Firepit | W/D
Top guest favourite

Cottage in Union Pier
5 out of 5 average rating, 31 reviewsCharming Cottage - Hot Tub, Sauna, Large Yard

Home in Lakeside
5 out of 5 average rating, 3 reviewsLee's Cottage in Lakeside
Guest favourite

Cottage in Lakeside
4.98 out of 5 average rating, 41 reviewsLakeside House w/ Private Beach Access
Guest favourite

Home in Union Pier
5 out of 5 average rating, 41 reviewsModern Beachfront Home With Hot Tub , The Nest
Superhost

Cottage in Lakeside
4.89 out of 5 average rating, 75 reviewsCharming Writer’s Cottage on 10 Acres of Land
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Northeast Ohio Holiday rentals
- Platteville Holiday rentals
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- Detroit Holiday rentals
- Louisville Holiday rentals
- Columbus Holiday rentals
- Southern Indiana Holiday rentals
- Cleveland Holiday rentals
- Cincinnati Holiday rentals
- Lincoln Park
- Millennium Park
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- 875 North Michigan Avenue
- 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
- Deep River Waterpark
- Chicago Cultural Center
- DuSable Museum of African American History
- Adler Planetarium
- Chicago History Museum
- Buckingham Fountain
- Woodlands Course at Whittaker
- The Dunes Club