
Cottage vacation rentals in Lakeside
Find and book unique cottages on Airbnb
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
Cottage rentals with a hot tub

Charming Cottage on the Lake

The Cottage of Harbor Country - Close to it all!

The Lemonade Cottage, New Buffalo. Walk to beach!

Cottage near Hagar Beach Pet friendly with Hot tub

Hot tub! Red Tin Cottage of Harbor Country!

Blueberry Fields/ House and Retreat

Lake View Cottage

Michiana Cottage
Pet-friendly cottage rentals

Northwind Llama retreat 'Loft Cottage'

Bright Designer Warren Dunes Maple St Beach House

The Koi Cottage - Union Pier- Dog Friendly!

Vintage Romance Finds Cozy Charm at Depot Cottage

New Buffalo retreat - Perfect year-round getaway!

The Rail House, Lakeside MI

DKM Cottage - 15 minute walk to Lake Michigan

Family friendly new house in woods /great for kids
Private cottage rentals

Family Friendly Private Beach Home New Carlisle

Rosie’s Cottage close to Warren Dunes (w pool)

2 updated Cottages for one price close to beach

Cozy 2 bedroom cottage steps from Lake Michigan

Elephant Walk- Cottage 5

Charming 3BD cottage-1 block to Journeyman & town

Van Auken Lake cottage rental

Lakefront A-Frame - Beach, Kayaks & Pontoon Rental
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- Millennium Park
- Navy Pier
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Lincoln Park
- Washington Park Zoo
- Museum of Science and Industry
- Willis Tower
- Lincoln Park Zoo
- Potato Creek State Park
- Silver Beach Carousel
- Chicago Cultural Center
- Adler Planetarium
- Chicago History Museum
- Buckingham Fountain
- DuSable Museum of African American History
- Deep River Waterpark
- Culver Academies Golf Course
- Maggie Daley Park
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes