Waterfront vacation rentals in North Side
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in North Side
Guests agree: these waterfront rentals 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
4.93 out of 5 average rating, 46 reviewsThe Holiday House by the Lake! 2br/2bth
Dec 4 – 11
Apartment in Chicago
4.86 out of 5 average rating, 29 reviewsElegant 2-bed/2-bath in the heart of Uptown
Nov 18 – 25
Apartment in Evanston
4.86 out of 5 average rating, 29 reviewsModern|Spacious|New Renovation|1BR|Evanston
Jun 18 – 25
Apartment in Chicago
4.82 out of 5 average rating, 87 reviewsCozy 1 BR Apartment in South Loop
Jul 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, 124 reviewsExecutive Apartment on Lake Michigan with parking
Sep 9 – 16
Apartment in Evanston
4.78 out of 5 average rating, 127 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Sep 25 – Oct 2
Apartment in Chicago
4.54 out of 5 average rating, 39 reviewsHUGE & BRAND NEW BEACH Apartment is Ready For You!
Oct 22 – 29
Waterfront house rentals
Home in Chicago
5.0 out of 5 average rating, 53 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Sep 19 – 26
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
Aug 13 – 20
Home in Deerfield
4.96 out of 5 average rating, 26 reviewsLake Forest Country Estate
May 23 – 30
Home in Barrington
5.0 out of 5 average rating, 26 reviewsON RIVER Barrington Home + Deck & Views
Mar 2 – 9
Home in Westmont
4.95 out of 5 average rating, 22 reviewsWestmont,Il 4/3 on the Lake
Oct 16 – 23
Home in Schaumburg
4.89 out of 5 average rating, 44 reviewsSprawling private fenced home with pond view!
Oct 22 – 29
Home in Chicago
4.74 out of 5 average rating, 23 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
Dec 28 – Jan 4
Home in Chicago
4.82 out of 5 average rating, 61 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Sep 26 – Oct 3
Waterfront condo rentals
Condo in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
Dec 29 – Jan 5
Condo in Chicago
4.96 out of 5 average rating, 56 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Jul 22 – 29
Condo in Chicago
4.67 out of 5 average rating, 170 reviewsStudio flat in the heart of Chicago's Gold Coast
Aug 3 – 10
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Nov 3 – 10
Condo in Chicago
4.89 out of 5 average rating, 9 reviewsCozy Studio 1BR Apt near the lake on the Northside
Sep 3 – 10
Condo in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Mar 12 – 19
Condo in Chicago
4.75 out of 5 average rating, 12 reviewsSpacious Wicker Park Hideaway with Parking!
Mar 6 – 13
Condo in Chicago
4.8 out of 5 average rating, 10 reviewsLovely 1 Bedroom with Fireplace and Home Office
Jul 10 – 17
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Waterfront rentals Downtown Chicago
- Waterfront rentals Milwaukee
- Waterfront rentals Illinois
- Beachfront rentals North Side
- Rentals with a balcony North Side
- Family-friendly rentals North Side
- Bed and breakfasts North Side
- Rentals with a fire pit North Side
- Smoking-friendly rentals North Side
- Condo rentals North Side
- Guesthouse rentals North Side
- Rentals with a hot tub North Side
- Monthly Rentals North Side
- Loft rentals North Side
- Rentals with an EV charger North Side
- Rentals with a fireplace North Side
- Townhouse rentals North Side
- Rentals with pools North Side
- Private suite rentals North Side
- House rentals North Side
- Pet-friendly rentals North Side
- Rentals with breakfast North Side
- Apartment rentals North Side
- Rentals with outdoor seating North Side
- Rentals with beach access North Side
- Hotel rentals North Side
- Rentals with lake access North Side
- Fitness-friendly rentals North Side
- Kid-friendly rentals North Side
- Rentals with a patio North Side
- Rentals with a washer and dryer North Side
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom