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Rogers Park holiday rentals

We found 185 holiday rentals — enter your dates for availability

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Dates

Calendar
Flexible dates

September 2025

October 2025

Discover a selection of 40 apartments, 15 flats and other holiday rentals in Rogers Park that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include a hot tub and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Rogers Park

Showing deals for:19 Dec - 26 Dec

Very good

(9 reviews)

✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨

Evanston, IL

8% off

for 7 nights, 1 home

S$519 per night

includes taxes & fees

Exceptional

(24 reviews)

3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville

Chicago, IL

12% off

for 7 nights, 1 room

S$889 per night

includes taxes & fees

Exceptional

(52 reviews)

Cozy Northside Apt near Transp, Loyola&NW, Beach, Sep Entrance&Free Street Park

Chicago, IL

7% off

for 7 nights, 1 apartment

S$264 per night

includes taxes & fees

Exceptional

(17 reviews)

Classic Chicago 2 Flat transformed into a Parisian plant lovers paradise

Chicago, IL

7% off

for 7 nights, 1 home

S$453 per night

includes taxes & fees

Exceptional

(38 reviews)

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Evanston, IL

6% off

for 7 nights, 1 apartment

S$305 per night

includes taxes & fees

Exceptional

(30 reviews)

Great Evanston Home- great for traveling families! Parking Included

Evanston, IL

16% off

for 7 nights, 1 apartment

S$730 per night

includes taxes & fees

Exceptional

(28 reviews)

100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!

Chicago, IL

7% off

for 7 nights, 1 home

S$569 per night

includes taxes & fees

Large kitchen with open floor plan, hardwood floor throughout.

Exceptional

(184 reviews)

Walking distance to restaurants, shops and Lake Michigan,

Chicago, IL

7% off

for 7 nights, 1 apartment

S$382 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Rogers Park

Premier Host

Roomy 3BR Apartment near Beach

Sleeps 6 · 3 bedrooms · 1 bathroom

Cozy Northside Apt near Transp, Loyola&NW, Beach, Sep Entrance&Free Street Park

Sleeps 6 · 1 bedroom · 1 bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Rogers Park?

The most sought-after types of holiday rentals in Rogers Park are condos. Looking for something different? Vrbo offers a variety of options to match our guests' needs, so you'll see holiday properties in all sizes and shapes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a holiday rental in Rogers Park?

Length of stay, property type and season are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your dream escape. From quaint country cottages to expansive luxury villas, all Vrbo holiday rentals offer amazing value.

How much does it cost to rent a beach house in Rogers Park?

The average price for a holiday rental by the beach in Rogers Park depends on when you're going and the style and size of property you're looking for. You can easily and quickly find prices on Vrbo by entering your preferred travel dates and destination. Then use the handy filters to select the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.

Are there pet-friendly holiday rentals in Rogers Park?

With 14 properties that welcome pets, your furry best friend can also come along on your Rogers Park getaway. Use the filter tool to search our pet-friendly holiday rentals and find your pawfect pad on Vrbo.

What are popular rental amenities in Rogers Park?

When it comes to rental amenities that guests are searching for in Rogers Park, a firepit, a lake view and nearby museums rank the highest. With Vrbo holiday rentals, you'll enjoy choices to suit your style and taste, whether you're going away with relatives, friends or even pets.

Are there large group holiday rentals in Rogers Park?

Yes, you can pick from one of 11 properties in Rogers Park that can sleep five or more people. From family get-togethers to a special event, these stays have ample space to kick back with the people you love.

Are there holiday rentals in Rogers Park that welcome kids?

Rogers Park has 14 family-friendly holiday rentals to pick from. And tracking down a stay that welcomes kiddos is easy with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll enjoy access to perks and conveniences such as multiple bedrooms, full kitchens and yards.

What are the top attractions for families in Rogers Park?

There's a ton of amazing things to see and do with the family in Rogers Park, such as:

Navy Pier
Chicago Riverwalk
Lincoln Park Zoo

Can I find two-bedroom holiday rentals in Rogers Park?

Rogers Park has five two-bedroom holiday properties that you can choose from. Go for a holiday home with all the privacy and comfort you're looking for at a fantastic price on Vrbo.

Are there holiday rentals with WiFi in Rogers Park?

Whether you want to keep up with the headlines, look over emails or surf social networks, there are 10 holiday homes with WiFi in Rogers Park. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find holiday rentals with air conditioning in Rogers Park?

Pick your travel dates and then make use of the filters to look for holiday rentals with ac in Rogers Park on Vrbo. With 13 air-conditioned properties available, you can enjoy a cool and comfortable trip.

How old do you have to be to rent a holiday rental in Rogers Park?

We recommend you check with the Rogers Park holiday rental you're looking at on Vrbo as the minimum age varies. However, generally it's 16, 18 or 21.

How long can I rent a holiday rental in Rogers Park for?

The length of time you can book a holiday rental in Rogers Park is down to the property. Just enter your selected travel dates to look at a list of options offering extended stays. With plenty of amenities such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get somewhere perfect to call your home away from home in Rogers Park.