Lakefront Vacation Rentals
on the Chain O' Lakes
Three fully managed properties 50 miles from Chicago. Book direct and skip the platform fee! Or, talk to us about putting your lakefront property to work.
Lake County, IL · Chain O' Lakes · Antioch · Spring Grove · Fox Lake
50 miles from Chicago · 45 min from O'Hare · 65 min from Milwaukee · One of Illinois' highest-demand STR markets
Managed Properties on the Chain O' Lakes
Three distinctive lakefront properties, each fully managed by Dockside. Every one is available for direct booking.
Petite Lake Resort
Nordic cedar sauna, private boat launch, sandy beach, dog-friendly. Modern lakefront living at its finest.
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Cypress Resort & Marine
Historic 1940s cypress cottages, 480ft private beach, hot tub, and a 125-guest Boat House wedding venue.
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Grandview Estates on Lake Catherine
A 1942 lakefront estate with private dock, hot tub, seasonal Boat House, and Coach House. An adjacent 2-bedroom cottage sleeps 4–5 for extended groups.
View Property →Every Property is Professionally Managed. That's the Difference.
Dockside-managed properties aren't just listed. They're run. That means a better stay for every guest and a better return for every owner.
No Surprises at Check-In
Every listing is photographed by professionals. What you see is what you get, accurate photos of every room, view, and amenity. For owners, professional imagery means more clicks and stronger nightly rates.
Hotel-Standard Turnover
Vetted cleaning teams on every stay, inspected after every turnover, fresh linens throughout. Guests arrive to a property that's genuinely ready. Owners build the consistent reviews that drive repeat bookings.
Real People, Real Response Times
Questions before you arrive, issues during your stay, covered by a local team that knows these properties. For owners, 24/7 guest communication handled end-to-end means you never field a late-night call.
Maintained Year-Round
Every property is actively cared for between seasons. If something breaks, our local vendor network fixes it before the next guest arrives. Owners get maintenance coordination without ever picking up the phone.
Book Direct and Keep the Savings
Booking through Dockside directly skips the 12-16% Airbnb guest service fee. Guests pay less. Owners earn a higher share of the same nightly rate. Everyone wins except the platform.
Frequently Asked Questions
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What's the difference between booking here vs. Airbnb?
When you book directly through Dockside you skip Airbnb's 12–16% guest service fee and pay the same nightly rate. You also get direct communication with the local team that manages the property, not a platform chatbot. Same property, lower total price, better support. -
Where exactly are the properties located?
All three properties are on the Chain O' Lakes in Antioch, Illinois, Lake County. Petite Lake Resort and Cypress Resort & Marine are both on Petite Lake. Grandview Estates is on Lake Catherine. All are within 5 miles of each other and within 50 miles of Chicago. -
How far in advance should I book?
Summer weekends on the Chain O' Lakes book 60–90 days out, especially Memorial Day through Labor Day. Holiday weekends (4th of July, Labor Day) book even earlier. For shoulder season (spring and fall) you often have more flexibility, but popular weekends around Venetian Night, the fishing derbies, and fall foliage go fast. -
Are the properties dog-friendly?
Yes. Petite Lake Resort and select cottages at Cypress Resort & Marine welcome well-behaved dogs with prior notice. These properties charge a flat pet fee of $50 per dog for the entire stay (2 dog maximum) and include a welcome dog basket. Check the individual property page or contact us directly to confirm policies before booking. -
What's included with a stay?
All properties include full access to their shared amenities at no extra charge. Petite Lake Resort includes the Nordic cedar sauna, private boat launch, sandy beach, and kayaks. Cypress Resort includes the 480ft beach, shared hot tub, kayaks, SUPs, and canoes. Grandview Estates includes private waterfront access and dock on Lake Catherine. See each property page for the full list. -
Can I bring my boat?
Yes. Petite Lake Resort has a private boat launch with trailer parking. The Chain O' Lakes system connects 15 lakes, so you can boat extensively from any of the properties. If you don't have a boat, our local partner OTC Rentals offers tritoon and pontoon rentals near the resorts.
What Our Guests Say
"The grounds are perfect for a family trip. So many helpful amenities — life vests, floaty toys, hot tub... it's just incredibly above-and-beyond. We've already made it a family tradition!"
"The cottage was wonderful, comfortable, clean, and relaxing. The location is perfect with the best beach and every water toy we could have wanted. We cannot say enough about the hospitality!"
"Our stay at the Cypress Beach cottage was great! We got to enjoy the beach, paddle board with our dog, and even book a beach massage. We will absolutely be back!"
What Does a Managed Lake Property Actually Earn?
A typical 3-bedroom lakefront home under full Dockside management on the Chain O' Lakes. Based on comparable properties in our portfolio.
Numbers based on a 3BR lakefront home at 25% management fee. Actual results vary by property, amenities, and season.
The Dockside Blog
Market data, management tips, and guest guides for the Chain O' Lakes.
How Much Can You Earn Renting Your Chain O' Lakes Property? (2026 Data)
Revenue ranges by bedroom count, waterfront access, and seasonal demand. Real numbers from the Chain O' Lakes market.
Read the Guide →7 Things to Ask Before Hiring a Vacation Rental Manager on the Chain O' Lakes
Fee transparency, local knowledge, cleaning standards, and more. What separates great managers from average ones.
Read the Guide →First Time on the Chain O' Lakes? The Complete Guest Guide
Lakes, fishing, boating, restaurants, and seasonal events. Everything first-timers need to know before they arrive.
Read the Guide →Ready to See What Your Property Could Earn?
Tell us about your property and we'll put together a custom revenue projection based on comparable managed properties on the Chain O' Lakes. No commitment required.