.The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining

Greetings from The Pleasant Hill Cottage Keepers!

Built in the 1930s, she carries nearly a century of stories within her charactered bones, stories she wears with pride. From the moment you arrive, there’s a quiet sense you’ve stepped out of time. Even the crabapple tree arches its limbs over the pathway to greet you, while morning light dances through the leaves & the boxwood-lined stairway as they guide you toward her custom arched castle-like front door.

Cross the threshold, and it feels as though the warmth of the past 100 years gently wraps around you, welcoming, familiar, and timeless. Guests often say it’s like stepping into a vintage dollhouse, where every perfectly placed detail whispers stories of the past, hoping to awaken the childlike wonder you may have tucked away. Here, curiosity finds room to wander, imagination is nourished, and the clock loosens its grip, letting each moment linger longer.

The Pleasant Hill Cottage unfolds across three levels, with three bedrooms (in addition, a quaint attached sleeping room with 2 twin beds "The Rapunzel Room") and three bathrooms. Each bath and the kitchen have been lovingly renovated to honor her original charm while offering modern comforts. The creaks in the floor remain, an intentional choice, adding a familiar soundtrack of a home well-lived in and well-loved for decades.

Nature wraps around her in every season. Wild gardens bloom like paintings beyond each window, mature trees stand guard, and a neighborhood cat may sun itself in the distance in the afternoon. Mornings begin with a chorus of birdsong and evenings are for sunsets. The golden glow floods it's light on the feont porch, through the front door, living room, dining room, and the sweet “Rapunzel Room's” arched window.

The Pleasant Hill Cottage welcomes you with a quiet enchantment, wrapping you in her timeless embrace. We hope you depart with a heart full of inspiration, a spirit restored, and a gentle balance that lingers long after you’ve returned home.

Should you choose her as your haven, we’d be honored to weave your chapter into her endless tale...

a story nearly 100 years in the making…
and still unfolding strong...

with warmth & gratitude,
Your Cottage Keepers