Owner Direct Vacation
Rentals in Near North Side
The Best Owner Direct Vacation Rentals in Near North Side. Explore thousands of vacation home rentals, large cabins, and villas near Near North Side
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Explore the Best Near North Side Vacation Homes
Looking for the perfect place to stay in Near North Side? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Near North Side character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Near North Side Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Near North Side
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Wheelchair Accessible
- Accessibility
- Air Conditioner
- Parking
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Accessibility
- Security/Safety
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Accessibility
- Security/Safety
Popular Neighborhoods for Near North Side Vacation Rentals
What are the best areas to stay in Near North Side
Discover the top neighborhoods in Near North Side and choose a place that suits your stay.
Thursday Jan 22
Near North Side, Chicago
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Near North Side vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Near North Side
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How to Reserve Your Near North Side Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Near North Side Vacation Rental FAQs
1. What are the top vacation rentals in Near North Side?
There are a lot of options in Near North Side. If you plan on staying in the Near North Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Near North Side:
- Magic Factory Loft 2West
- Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
- Brilliant Downtown Chicago 3-Bedroom Condominium
- Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
- City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
- Gorgeous 3BR River North Condo - Free Parking
- Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.
- LOCATION! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
- Downtown Guild #3 | Mag Mile Gold Coast The Lake!
2. How many vacation rentals have private pools in Near North Side?
There are 22 vacation rentals with private pools near Near North Side. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Near North Side are best for families?
If you are looking for a family-friendly vacation home in Near North Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Near North Side:
4. How many vacation rentals are available in Near North Side?
Currently, the total number of properties listed in 2026 is over 1214 in the Near North Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Near North Side.