Vacation rentals in Lake County

Re-imagined 1880s cottage by Highwood, Metra, Lake

Step inside Step back in time Cozy, 1880 built, re-imagined, ravine edged garden cottage Your home away from home. Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage yet modern, Mere Cottage has so much to offer. Inside: You'll enjoy updated amenities in harmony with a distinctive vintage charm. The common area has an open layout, perfect for socializing. The kitchen and pantry (my favorite room!) are new from top to bottom and are fully stocked with any cooking gadgets you may need. Two bedrooms are joined by a Jack & Jill bathroom. The living room has a sofa that pulls out into full size bed. Outside: Jordan and I had fun redesigning the grounds from front to back. Enjoy the front garden from the rocking chair on our wrap around porch. Out back we've added a vegetable and perennial garden for you to take in. Dinner out on the back deck overlooking the garden is highly recommended! Guests have access to the entire home and grounds. Jordan and I live in the neighborhood and will be available if you need us! Our cottage is located in Highland Park, about 25 miles north of Chicago on Lake Michigan. We like to think we have the best of both worlds- being in a quiet residential neighborhood with walking access to numerous amenities right around the corner. We're a quick 5 minute walk to Highwood (the north shore’s restaurant district) and an 8 minute walk to the Metra train that can take you from Chicago to Kenosha and any place in between. We're also right on the North Shore bike path (bring your bikes!). Fort Sheridan is also close by and worth exploring for its interesting history, architecture, and nature trails. On foot: Many errands can be done on foot. We have some of the best restaurants and watering holes north of Chicago within walking distance. There is also a Walgreens convenience store 2 blocks away. By car: Getting around by car is also easy. Parking is readily available almost anywhere you'll visit. You can get to downtown Chicago in 30 minutes in ideal traffic. Train: The Metra (our train system) can also conveniently get you to and from various attractions including downtown Chicago (a scenic 45 minute ride), Ravinia music venue, the Chicago Botanic Gardens, Great Lakes Naval Base and many more. Bike: Pack your bikes! We're located on the north shore bike trail. Head north on the trail to check out the beautiful Fort Sheridan, Lake Forest, and quaint Lake Bluff. Head south to Ravinia, Chicago Botanic Garden, and numerous other beautiful villages along Lake Michigan. I bike often and will gladly point you to some great hidden gems! If you're flying into O'hare, we recommend taking an Uber to our cottage. We're about a 30 minute drive from the airport. Six Flags Great America is also a 25 minute drive away. Keep in mind that the bathroom is a Jack & Jill and is accessed from either bedroom. There is no access from the common area, so it could pose an issue at night when sleeping our max number of 6. Please keep things tidy and wash any dishes used during your stay. Out of respect for our neighbors (this home is located in a quiet residential neighborhood), no parties or large gatherings are allowed. No pets allowed.

Family · Location · Backyard

Cozy Mother inlaw Suite. Private. Next to beach.

30 minutes away from the Navy Base(Graduates). 5 minutes away from the newly renovated Beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags. This Mother in Law suite has tons of natural light. Private access and no shared indoor space. Safe and quiet neighborhood with plenty of wildlife right in the back yard. For nature lover’s this unit is close to the beach and there are walking trails nearby.

Location · Family · Walkability

Cozy 2 bedroom home with a study

This newly remodeled chicken Coop turned into a 2 bedroom A frame home is fifty miles from Milwaukee, forty-seven miles from Chicago, and ten miles from the Naval Station. We are a couple minutes away from City of Hope, Six Flags Great America, Bristol Renaissance Faire, Great Wolf Lodge, Casinos, and the beach. There is also a Target and Starbucks down the road, what more can you ask for! The stairs to the bedrooms are steep and narrow so please be careful. Please enjoy the home to yourselves

Location · Family · Comfort

Kalo House | Mid-Century Modern Retreat with Pool

A beautifully preserved mid-century modern home with pool designed by noted architect Edward Humrich. The Kalo House blends iconic architecture with warm, curated interiors. Clean lines, expansive windows, and thoughtful design throughout. Peaceful and stylish, it’s the perfect retreat for design lovers visiting Chicago’s North Shore, Lake Michigan, or nearby Great Lakes Naval Station. Thoughtfully, curated and hosted with care…Perfect for Navy graduation stays and gathering families together.

Location · Family · Sleep quality

Modern 4BR Lake Retreat • Walk to Beach & Main St

Lakeside Haven, a 4BR retreat on Bangs Lake. Steps from Main Street’s dining, shopping, and beaches, this modern home offers:
 🌊 Lake views & open living spaces 💻 High-speed Wi-Fi & workspace 🍳 Fully equipped kitchen & laundry 🚤 Nearby hiking, boat rentals, & events 🛏️ King & queen beds 🪟 Blackout screens Perfect for families, Navy graduations, and long stays. Enjoy the Triathlon, farmers market, cruise nights, ice fishing derby, and more. Dates fill quickly in every season. Book today!

Location · Family · Sleep quality

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Value · Family · Cleanliness

"Magnolia Farmhouse" inspired 4-bedroom home

Enjoy a spacious, open floor plan on a quiet, dead-end street! This "Magnolia Farmhouse" inspired 4-bedroom ranch home is set on one acre. Located 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! Minutes away for the Great Lakes Naval Station (9mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here, make Boyce Lane your home away from home today!

Location · Family · Parks

Historical Hideaway near Naval Base

Step back in time at The Pilothouse, a charming historic 1854 home located in Waukegan’s historical district, just 12 minutes from Naval Station Great Lakes. This beautifully preserved home features Navy and aviation-themed décor, 3 cozy bedrooms, a sunroom filled with lush plants, a fully equipped kitchen, and a spacious backyard with a gazebo, large patio, and grill—ideal for relaxing outdoors. Experience the perfect blend of vintage charm and modern comfort in this serene retreat.

Location · Family · Getting around

Your relaxing stay in Highland Park

Whether you are looking to escape the city hustle and bustle, visiting Lake Forest College, the Naval Station or moving cross country, our bright and spacious suite is the perfect spot to check in and relax for a few nights. Featuring a separate entrance and a beautiful, private newly remodeled bathroom. 43 4K Smart HDTV with Netflix and Prime and super fast WiFi available for streaming. Kitchenette with a microwave, mini fridge, sink and cups/plates/010/053/2026cutlery.

Location · Family · Getting around

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Family · Location · Accuracy

Wonderful Mineola Bay Lakefront Cottage 4adu+4kids

Book a romantic weekend or bring the whole family to this cozy, clean and well-appointed lake house that has plenty of room for fun. Embrace lake-life at its finest when you call this Fox Lake cottage on Mineola Bay your home away from home! We have a dock to park your boat, so bring it. Access to restaurants, bars, convenience and grocery stores, boat launches and more. Or hang out and soak in the sunshine while paddle boarding, boating, kayaking, swimming and nature hikes.

Location · Family · Getting around

King Suite | Sleeps 8 | Near Navy Base & Six Flags

Welcome to your peaceful woodland escape right in the heart of Waukegan! Backing directly onto a lush, private nature preserve, this freshly updated 3-bedroom, 2.5-bath home offers the ultimate blend of suburban convenience and serene privacy. Whether you are in town celebrating a Navy Boot Camp graduation, visiting Six Flags, or simply seeking a quiet family getaway, this 1,800+ sq ft retreat gives your group plenty of room to spread out, relax, and recharge.

Location · Family · Bathroom