Chain O' Lakes, IL

Chain O' Lakes Vacation Rentals

Browse our managed portfolio of lakefront properties near Chicago. Book direct to bypass platform service fees and save up to 16%.

50 miles from Chicago  ·  Lake County, IL  ·  Antioch & Spring Grove

Lakefront homes, historic cottages, and private lake retreats, all on the Chain O' Lakes system

3
Managed Properties
15
Connected Lakes
$150–$600
Per Night
5★
Guest Reviews
Save 12–16% Instantly

Avoid Platform Markup Fees

When you book through major online travel agencies like Airbnb or VRBO, you pay an extra 12–16% guest service fee on top of the nightly rate. When you book directly through our official resort sites, that fee disappears completely. You get the exact same property, the exact same host team, and the exact same experience—for less.

  • Zero Guest Service Fees: The price you see is the price you pay.
  • Best Rate Guarantee: We match or beat any rate found on platform listings.
  • Local Expertise & Support: Deal directly with our lakefront experts.
  • Flexible Policies: More accommodating cancellation and rescheduling terms.
Browse Properties & Book Direct

Platform vs. Direct Cost Comparison

Here is what the exact same 3-night stay looks like at checkout:

Nightly Rate (3 nights) $300 × 3 = $900
Airbnb Guest Service Fee (~14%) +$126
Total via Platforms $1,026
Total Booking Direct $900

You Save: $126 on this stay!

Easy 3-Step Process

How to Secure Your Direct Savings

1

Choose Your Lake Vibe

Explore our distinct properties listed below: the modern wellness-focused Petite Lake Resort, the historic beach cottages of Cypress Resort & Marine, or the expansive Grandview Estates.

2

Search Availability Instantly

Enter your dates in the search bar above to see live availability across our portfolio, or check dates directly on the specific resort websites.

3

Reserve Securely with No Middleman

Use our official, secure booking checkout links. Your payment will be processed securely, and your custom Guest Guide and access codes will be emailed to you instantly.

All Managed Properties

All Managed Properties

Three distinct lakefront experiences on the Chain O' Lakes. Each property has its own character, choose the one that fits your group.

Petite Lake Resort beachfront lake view, Petite Lake Antioch IL
Modern Lakefront Homes

Petite Lake Resort

📍 Petite Lake  ·  Antioch, IL

5 Rental Homes Up to 8 Guests $150–$450/night 4 Seasons

Modern lakefront vacation homes on Petite Lake with a 6-person Nordic cedar sauna, private concrete boat launch with trailer parking, and direct access to the Chain O' Lakes system.

Nordic Sauna Boat Launch Sandy Beach Dog Friendly Kayaks Fire Pit
Cypress Resort 480ft private beach on Petite Lake, Antioch IL
Historic Cottages

Cypress Resort & Marine

📍 Petite Lake  ·  Antioch, IL

7 Historic Cottages Up to 10 Guests $175–$600/night

Historic 1940s cypress wood cottages on Petite Lake with a 480ft private beach, shared hot tub, and a 125-guest Boat House wedding and event venue.

480ft Beach Hot Tub Wedding Venue Dog Friendly Kayaks Fire Pit
Grandview Estates on Lake Catherine waterfront, Chain O' Lakes Antioch IL
Historic Lakefront Estate

Grandview Estates on Lake Catherine

📍 Lake Catherine  ·  Antioch, IL

6 Bedrooms + Cottage Up to 21 Guests 192ft Waterfront

A 1942 lakefront estate on Lake Catherine with 192 feet of private waterfront, hot tub, private dock, seasonal Boat House, and Coach House apartment. An adjacent 2-bedroom cottage sleeps 4-5 for extended groups.

Hot Tub Private Dock Boat House Dog Friendly Fire Pit Fireplace
Booking Questions

Common Booking Questions

Quick answers before you reserve your Chain O' Lakes getaway.

  • How do I book one of the Dockside-managed properties?

    Each property has its own direct booking page: petitelakeresort.com, cypressofantioch.com, and Grandview Estates (plus the Grandview Cottage). We recommend booking direct to avoid the platform service fee, you'll work directly with our team and get the same high-quality stay at a lower total cost.

  • What's included in the rental, do I need to bring anything?

    All Dockside-managed properties come fully equipped: linens, towels, a fully stocked kitchen, cookware, coffee, and a welcome kit with starter supplies. Outdoor amenities like kayaks, paddleboards, and fire pit wood are included at properties where they're listed. You don't need to bring anything beyond personal items and groceries for your stay. Each property listing specifies exactly what's included, check the amenities section before booking if you have specific questions.

  • What's the check-in and check-out process?

    All properties use keypad or smart lock entry, no physical key pickup required. You'll receive a unique access code and detailed check-in instructions via email a few days before your arrival. Standard check-in is 4:00 PM and check-out is 10:00 AM. Early check-in or late checkout may be available depending on the booking calendar, reach out to us at docksidevacation@gmail.com and we'll do our best to accommodate. Our team is available by phone and text throughout your stay.

  • Can I bring my boat?

    Yes, several of our properties have boat launch or slip access. Petite Lake Resort has a private concrete boat launch with trailer parking, making it ideal for guests trailering their own boat. Cypress Resort guests have access to Petite Lake via the resort's water frontage. Note that the Chain O' Lakes is a no-wake zone in certain areas and all watercraft must comply with Illinois DNR boating regulations. Fishing licenses are required for anyone 16 and older fishing Illinois waters.

What Are You Looking For?

Can't Find What You're Looking For?

Guests: visit our Area Guide for more on what to do in the Chain O' Lakes region. Property owners: find out what your home could earn under professional management.

Explore the Area Guide I'm a Property Owner →