Waterfront vacation rentals in North Side
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Top-rated waterfront accommodations in North Side
Guests agree: these waterfront accommodations 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 North Side waterfront rentals
Waterfront apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 29 reviewsElegant 2-bed/2-bath in the heart of Uptown
Oct. 29 – Nov. 5
Apartment in Chicago
4.82 out of 5 average rating, 87 reviewsCozy 1 BR Apartment in South Loop
Jul. 3 – 10
Apartment in Evanston
4.86 out of 5 average rating, 28 reviewsModern|Spacious|New Renovation|1BR|Evanston
Jun. 18 – 25
Apartment in Lisle
4.65 out of 5 average rating, 78 reviewsTranquility and comfort in private condo
Aug. 11 – 18
Apartment in Chicago
4.94 out of 5 average rating, 123 reviewsExecutive Apartment on Lake Michigan with parking
Oct. 30 – Nov. 6
Apartment in Evanston
4.78 out of 5 average rating, 127 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Aug. 6 – 13
Apartment in Chicago
4.54 out of 5 average rating, 39 reviewsHUGE & BRAND NEW BEACH Apartment is Ready For You!
Sep. 9 – 16
Apartment in Chicago
4.6 out of 5 average rating, 133 reviewsBoutique Flat in Lincoln Park with Free Parking!
Nov. 7 – 14
Waterfront house rentals
Home in Chicago
5.0 out of 5 average rating, 52 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Sep. 15 – 22
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
Sep. 21 – 28
Home in Highland Park
4.92 out of 5 average rating, 39 reviewsWitness Sunrise Over Lake Michigan
Oct. 1 – 8
Home in McHenry
5.0 out of 5 average rating, 3 reviewsThe Acorn @ Oaks on The Fox
Sep. 8 – 15
Home in Westmont
4.95 out of 5 average rating, 22 reviewsWestmont,Il 4/3 on the Lake
Jan. 25 – Feb. 1
Home in Barrington
5.0 out of 5 average rating, 25 reviewsON RIVER Barrington Home + Deck & Views
Jun. 4 – 11
Home in Deerfield
4.96 out of 5 average rating, 26 reviewsLake Forest Country Estate
May 18 – 25
Home in Wauconda
4.98 out of 5 average rating, 65 reviewsAdjacent to Bangs Lake and steps to Main Street
Aug. 5 – 12
Waterfront condo rentals
Condo in Chicago
4.87 out of 5 average rating, 92 reviewsUpscale Penthouse Private Balconies Amazing Views
Jul. 14 – 21
Condo in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
Oct. 20 – 27
Condo in Chicago
4.96 out of 5 average rating, 55 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Jul. 1 – 8
Condo in Chicago
4.67 out of 5 average rating, 169 reviewsStudio flat in the heart of Chicago's Gold Coast
Jul. 28 – Aug. 4
Condo in Chicago
4.89 out of 5 average rating, 9 reviewsCozy Studio 1BR Apt near the lake on the Northside
Sep. 2 – 9
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Jan. 29 – Feb. 5
Condo in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Mar. 8 – 15
Condo in Chicago
4.75 out of 5 average rating, 12 reviewsSpacious Wicker Park Hideaway with Parking!
Dec. 28 – Jan. 4
Destinations to explore
- Downtown Chicago Vacation rentals
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- Monthly Rentals North Side
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