Holiday Homes in North Side

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in North Side

Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!
Desk, iron/ironing board, free WiFi, bed sheets

Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay! The property was perfect for kids — safe, clean, and had plenty of space to play. The outdoor space is perfect for morning coffee, lounging, afternoon cocktails, and dinner under the stars. This location was unbeatable, close to everything we wanted to do. Couldn’t have asked for a better spot for a family getaway in the city. Highly recommend!"
Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!
Great 3 bedroom rental unit near Logan Square
Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (51)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, coffee machine, and microwave.

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (10)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym
New home w/view & party deck - 2nd Floor
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the outdoors.

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (22)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor
Lincoln Park Living - Suite 1
Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, sink, and coffee maker.

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (30)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1
Lincoln Park Living - Suite 2!
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and dishwasher.

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (39)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
Kitchen features white cabinetry, stainless steel appliances, and a herringbone-patterned backsplash.

Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

9.2 out of 10, Wonderful, (15)
"The house was very nice. Great neighborhood."
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
Chic and Spacious Bi-level 3BD in Bucktown!
Enjoy cooking in this well-lit kitchen with sleek cabinetry, a dishwasher, and oven.

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
10.0 out of 10, Exceptional, (6)
"This house was in a really convenient location - relatively close to the airport and within walking distance of downtown Bucktown. The home was very clean, the beds were really comfortable (not always the case in vacation rentals!), the communication was thorough and quick. It was perfect for me and my 3 friends!"
Chic and Spacious Bi-level 3BD in Bucktown!
Beautiful duplex in the heart of bucktown.
Terrace/patio

Beautiful duplex in the heart of bucktown.

10.0 out of 10, Exceptional, (2)
"Great location and host was very responsive."
Beautiful duplex in the heart of bucktown.
Wrigley Field/Lakeview -Entire Home- Large Groups!
Fully equipped kitchen with a stove, microwave, and coffee maker, featuring a granite countertop and black cabinetry.

Wrigley Field/Lakeview -Entire Home- Large Groups!

9.8 out of 10, Exceptional, (80)
"This property is clean, spacious and well appointed. It was better than the photos, and in an excellent location. It was very nice to have a parking space in the garage as well. Highly recommend."
Wrigley Field/Lakeview -Entire Home- Large Groups!
Spacious Luxury Townhouse - Old Town by AllSet Turnover
Kitchen features a large island with a sink and countertop, complemented by a staircase leading to an upper level.

Spacious Luxury Townhouse - Old Town by AllSet Turnover

8.4 out of 10, Very good, (18)
"Fantastic property in a charming location. Perfect walking score with top notch restaurants! Home was spacious with everything you need for a relaxing stay. Will return without a doubt! Easy communication with quick responses. "
Spacious Luxury Townhouse - Old Town by AllSet Turnover
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Stylish corner building with a unique architectural style, featuring a prominent entrance and multiple windows on each floor.

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

9.8 out of 10, Exceptional, (36)
"Great location. Great place to stay. "
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
BoHo House - A Chic, 1903 Chicago Workers Cottage
Enjoy al fresco dining and socializing in this outdoor patio area, featuring a barbecue grill, bench, and table.

BoHo House - A Chic, 1903 Chicago Workers Cottage

10.0 out of 10, Exceptional, (13)
"Highly recommend this property! It’s close to everything, our dog felt at home, and communication with the property owner was top notch! We will definitely stay here again when we find ourselves in Chicago next."
BoHo House - A Chic, 1903 Chicago Workers Cottage
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Enjoy the serene beach scene with a lighthouse in the distance and a pier extending into the calm sea.

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

9.8 out of 10, Exceptional, (172)
"Great place for our large group. Lots of room for the bridal girls to get ready for the wedding. "
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park Living - 3 Queen Beds - Sleeps 6!
Relax in an outdoor space with a wicker sofa, table, and chair.

Lincoln Park Living - 3 Queen Beds - Sleeps 6!

9.6 out of 10, Exceptional, (13)
"Nice area! Very clean! Would stay again"
Lincoln Park Living - 3 Queen Beds - Sleeps 6!
Stunning / Spacious 6BD Home + garage - Bucktown!
Kitchen with sleek design, featuring dark cabinets, stainless steel range hood, and white backsplash.

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (38)
"The house was very nice. It had a wonderful kitchen-living area for gathering. The location and neighborhood were perfect for our needs. We walked the area several times, finding great food and breweries. It was close enough to downtown as well."
Stunning / Spacious 6BD Home + garage - Bucktown!
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Relax in this stylish living room with a leather sofa, coffee table, and dining table.

The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

9.6 out of 10, Exceptional, (169)
"Great place to stay to experience Wrigley."
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Classic two-story building with arched windows and a prominent entrance, set amidst a charming urban setting.

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

9.8 out of 10, Exceptional, (25)
"Great location that was walking distance to everything we needed. There was more than enough room for our group and it was a comfortable stay."
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and wooden cabinetry.

Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.

10.0 out of 10, Exceptional, (13)
"Everything was easy and perfect. The house is conveniently located, spacious, perfect for a large family or group"
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.
Eddy House, Roscoe Village Haven
Kitchen features a stove, sink, and window with a doorway to another room.

Eddy House, Roscoe Village Haven

10.0 out of 10, Exceptional, (14)
"Great house . "
Eddy House, Roscoe Village Haven
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

Hotel Lincoln

Hotel Lincoln

10/10 Excellent
"We went to a concert at the Salt shed, and it was very close to hotel Lincoln. We loved the corner room we had overlooking Lincoln Park & Lake Michigan 😎"
Michael 1-night trip
Posted 2 days ago
Hotel Lincoln