Vacation Homes in Galewood, Chicago: House Rentals & More

Discover a selection of vacation rentals in Galewood that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the amenities you expect for your stay, which might include parking and a fireplace. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

Find the best place to stay - Galewood

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Sleeps 20 · 5 bedrooms · 2+ bathrooms

Top rated rentals - Galewood

Premier Host

Great Stay!

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Frequently asked questions

What is the most popular type of vacation rental accommodation in Galewood?

Houses are the most popular type of vacation rental in Galewood, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in all sizes and shapes. Browse our options to find your perfect pad.

How much does it cost to rent a vacation rental in Galewood?

The average price for a vacation rental in Galewood depends on a number of factors, like length of stay, property type and season. Whether you prefer a sprawling villa with space for extended family or a quaint cottage for just you and your sweetheart, just add your travel dates to find stays with fantastic value.

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

When you travel and the size and style of the property will help determine the cost of your beachside escape. Click on your Galewood travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you need.

What are the top attractions for families in Galewood?

Keep the kids entertained at these awesome family-friendly attractions in Galewood:

Humboldt Park Beach
Ukrainian National Museum
Chicago Center for the Performing Arts

How old do you have to be to rent a vacation rental in Galewood?

The minimum age can differ across properties on Vrbo, so be sure to look at the rules of the vacation rental in Galewood you're considering. But normally, it's 16, 18 or 21.

How long can I rent a vacation rental in Galewood for?

How long you can book a vacation rental in Galewood depends on the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With lots of features like full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find the perfect place to call your home away from home in Galewood.