Holiday rentals in Countryside Lake

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Top-rated holiday rentals in Countryside Lake

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

The exterior of a mid-century A-frame house showcases its striking triangular shape and steep slanted roof. Large glass doors provide a view of the interior, framed by an inviting deck area. Lush greenery surrounds the home, enhancing its connection with nature.

Cabin in Crystal Lake

4.92 out of 5 average rating, 25 reviews

The Fox Den / Midcentury A-frame

Our A-Frame is a mid-century gem with everything you envision in a cabin, plus all the comforts of home. It features a private dock with access to the Fox River and the Chain of Lakes, as well as direct entry to the Silver Creek Conservation Area. Located between the Fox River and the northern end of the Silver Creek Conservation Area, it’s only 1:15 from Chicago and 1:30 from Milwaukee. The ideal spot for a couple’s retreat, a small family adventure, or a solo escape to reconnect with nature.

Guest favourite

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Flat in West Dundee

4.91 out of 5 average rating, 185 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Top guest favourite

A modern two-story home is showcased from an aerial perspective, featuring a neatly trimmed yard and a fenced area. The property is positioned near a marina, with views of parked boats on the lake. An attached garage is visible, along with a spacious driveway.

Home in Wauconda

4.99 out of 5 average rating, 78 reviews

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!

Top guest favourite

The backyard features a well-maintained lawn surrounded by gray gravel. A patio area includes a dining table and umbrella. The house is painted in a soft blue, while a grill is positioned near the side of the house. A condo building is visible in the background.

Home in Wauconda

4.97 out of 5 average rating, 101 reviews

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

Guest favourite

Home in McHenry

4.97 out of 5 average rating, 31 reviews

Pet Friendly, Fenced In Yard, Lots to do Nearby!

Entire home included in your stay, big fenced in yard that is pet friendly! Updated, clean, 2 bedroom with 2 queen beds. 1 full bathroom. Laundry room with W/D. All hard surface flooring throughout (no carpet), kitchen has new appliances, dishwasher, coffee maker, toaster, microwave, fridge/freezer, quartz counters, all utensils stocked and available. There's a dining space with 4 chairs. Comfortable living room with couch and recliner, and wall mounted Smart TV. Patio, grill, outdoor space!

Top guest favourite

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

Guest suite in Riverwoods

4.95 out of 5 average rating, 504 reviews

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.

Guest favourite

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

4.96 out of 5 average rating, 238 reviews

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Top guest favourite

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

5 out of 5 average rating, 208 reviews

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!

Guest favourite

A charming bungalow exterior presents a warm facade with well-maintained landscaping. Features include a welcoming front staircase with wrought iron railings, potted flowers under large windows, and a flag hanging from the porch. A lush green lawn surrounds the home, enhancing its inviting presence.

Bungalow in Mundelein

4.87 out of 5 average rating, 247 reviews

Quaint Bungalow, near Great Lakes Naval Base

This cozy bungalow is located 41 miles north of Chicago; 60 miles south of Milwaukee, WI; and just 12 miles west of Great Lakes Naval Base. Nearby train stations make Chicago just a 45-minute train ride away. O'Hare Airport is a 30-40 minute commute from our home. Additional nearby sites include Great America, and shopping venues--from outlet malls in Gurnee and Kenosha, to quaint downtowns, like Libertyville. Location makes this home an ideal venue for Midwest sightseeing.

Top guest favourite

Home in Waukegan

5 out of 5 average rating, 7 reviews

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.

Top guest favourite

A charming cottage is framed by lush greenery and colorful flower planters. The white exterior features multiple windows, allowing ample natural light. A welcoming front porch leads to the entrance, adorned with patriotic bunting, inviting guests to enjoy the serene surroundings.

Cottage in Barrington

4.99 out of 5 average rating, 140 reviews

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Guest favourite

A cozy bedroom features a black metal bed frame adorned with soft pillows in pink and green hues. Textured white bedding is spread across the bed. Natural light filters through the large windows, complemented by light-colored curtains, and a nightstand sits beside the bed.

Guest house in Lake Forest

4.81 out of 5 average rating, 126 reviews

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage