Beachfront holiday rental in North Side
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Top-rated beachfront accommodation in North Side
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Holiday rentals for every style
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Popular amenities for North Side beachfront rentals
Pet-friendly beachfront home rentals
Room in Chicago
4.77 out of 5 average rating, 129 reviewsBasic accomodation equipped for short terms stays.
3–10 Jul
Apartment in Chicago
4.94 out of 5 average rating, 85 reviews420 at Cheltenham 4BR
2–9 Sep
Apartment in Chicago
4.86 out of 5 average rating, 100 reviewsRock Star Beach Pad on Lake Michigan with parking
30 Mar – 6 Apr
Apartment in Chicago
4.91 out of 5 average rating, 183 reviewsStone Mansion Sleeps 10-20 Free parking & TV
15–22 Nov
Apartment in Chicago
4.88 out of 5 average rating, 86 reviewsCannabis Condo 4BR
19–26 Oct
Townhouse in Chicago
4.8 out of 5 average rating, 155 reviewsHistoric lux Townhouse on Chicago's Gold Coast
18–25 Nov
Apartment in Chicago
4.94 out of 5 average rating, 124 reviewsExecutive Apartment on Lake Michigan with parking
8–15 Mar
Condo in Chicago
4.69 out of 5 average rating, 16 reviewsModern Duplex Condo With Advanced 4K LED TV’s/PS5
24 Nov – 1 Dec
Private beachfront home rentals
Condo in Chicago
4.9 out of 5 average rating, 235 reviewsMAG MILE 2/2 Gold Coast Gem (+Parking/Rooftop)
10–15 May
Condo in Chicago
4.87 out of 5 average rating, 242 reviewsMAG MILE 2/2 w/ Lake VIEWS! (+Rooftop)
17–24 Jun
Apartment in Evanston
4.98 out of 5 average rating, 42 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
9–16 Oct
Guest suite in Evanston
4.85 out of 5 average rating, 86 reviewsHistoric Manor House Private Guest Suite Evanston
12–19 Jun
Apartment in Evanston
4.8 out of 5 average rating, 83 reviewsModern|Aesthetic|2BR|Evanston|Near Beach
30 Oct – 6 Nov
Apartment in Evanston
4.71 out of 5 average rating, 113 reviews✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
23–30 Sep
Luxury beachfront home rentals
Apartment in Chicago
5.0 out of 5 average rating, 5 reviewsGold Coast Pristine Paradise 3BR/2BA. Free Parking
16–23 Jan
Townhouse in Chicago
5.0 out of 5 average rating, 210 reviewsSpacious 4-Level/4-Bedroom Townhouse in West Loop
10–17 Dec
Townhouse in Chicago
4.8 out of 5 average rating, 155 reviewsHistoric lux Townhouse on Chicago's Gold Coast
18–25 Nov
Home in Chicago
4.86 out of 5 average rating, 28 reviewsOnly Urban Beach House in Chicago
17–24 Feb
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Beachfront rentals Chicago
- Beachfront rentals Downtown Chicago
- Beachfront rentals Illinois
- Rentals with a balcony North Side
- Family-friendly rentals North Side
- Bed and breakfasts North Side
- Waterfront rentals 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 washing machine and dryer North Side
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