A nighttime city skyline reflected in a calm body of water, with illuminated buildings and a bridge.

Holiday Homes in North Side

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for North Side holiday homes

A cozy living room with a neon sign, a fireplace, a television, and a guitar.

1. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (44 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is €589
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

2. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is €628
includes taxes & fees
4 Nov - 5 Nov
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

3. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is €1,234
includes taxes & fees
11 Oct - 12 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

4. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
Premier 9BR Art Deco manor with garage.
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

5. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is €470
includes taxes & fees
5 Oct - 6 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

6. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is €555
includes taxes & fees
7 Oct - 8 Oct
Game Room • Fire-pit • Playground • Gym • Billiard
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

7. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (9 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is €895
includes taxes & fees
5 Oct - 6 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

8. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is €203
includes taxes & fees
27 Oct - 28 Oct
Master qtr close to nature & easy urban facilities
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

9. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is €277
includes taxes & fees
12 Oct - 13 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Room

10. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is €728
includes taxes & fees
7 Oct - 8 Oct
Arcade • Theater • Gym • Office • Sleeps 15
Communal lounging

11. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.0 out of 10, Wonderful, (4 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is €387
includes taxes & fees
15 Oct - 16 Oct
Cozy Studio Suite, Steps from River North & Shops
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

12. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €202
includes taxes & fees
26 Oct - 27 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

13. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
Chicago Riverhouse with private fenced in oasis
A single-story house with a covered porch, a front door, and a small garden area.

14. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern living room with a sectional sofa, a coffee table, and a TV.

15. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is €208
includes taxes & fees
5 Oct - 6 Oct
Attractive Coach House Apartment for rent in Oak Park.
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

16. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (63 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is €331
includes taxes & fees
6 Oct - 7 Oct
LUXE 3 BR, 2 BA + Hot Tub
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

17. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (31 reviews)
"Super clean great location short drive to everything we wanted to see!"
United States
eric p.
The price is €495
includes taxes & fees
14 Oct - 15 Oct
ENVITAE Hotel, 4BR Luxury Modern Apartments
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

18. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €278
includes taxes & fees
5 Oct - 6 Oct
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

19. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (24 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is €294
includes taxes & fees
3 Nov - 4 Nov
Cozy Home by O'Hare + EV Plug
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

20. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is €429
includes taxes & fees
4 Nov - 5 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top North Side Hotel Reviews

The Den Hotel

The Den Hotel

8/10 Good
"Good for a short stay, but would not consider this to be “a hotel’ as compared to the hospitality offerings typically available within the Select Services category of similar properties."
Anthony 3-night trip
Posted 22 hours ago
The Den Hotel

Find out more about North Side

North Side Holiday Homes information

Number of reviews
366
Accommodation
45 Holiday Homes
Lowest Price
€202
Highest Price
€1,234

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