The Pleasant Hill Cottage A Charmed Storybook Stay

Step into one of the North Shore’s most enchanting cottages, where every room feels as if an oil painting awoke from its canvas. Spend days on Lake Michigan’s luxury beaches, exploring its idyllic towns, the Botanic Garden, Bears Camp, the Naval Base, or hop a train to Chicago! Evenings glow w/ golden sunsets, candlelight & bonfires; stroll to Highwood’s live music, global dining & breweries or catch a star-lit concert at the legendary Ravinia! All set in the heart of a kind close-knit village.♡ The space *Greetings from The Pleasant Hill Cottage Keepers!* Built in the 1930s, she carries nearly a century of stories within her sturdy bones, that 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 the morning light dances through the leaves as the boxwood-lined stairway guides you toward her custom arched, castle feeling 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 feels like stepping into a vintage dollhouse, where every perfectly placed detail whispers stories of the past, in hopes of gently awakening the childlike wonder you may have tucked away. Here, curiosity finds room to wander, imagination is nourished, and the clock seems to loosen its grip, letting each moment linger The Pleasant Hill Cottage unfolds across three levels, with three bedrooms (including a quaint attached sleeping room) along with three bathrooms. Each bath and the kitchen have been lovingly renovated to honor her original bones while offering modern comforts. The creaks in the floor were intentionally left untouched... the soft, familiar soundtrack of a home well-lived and well-loved over the decades. Nature wraps around her in every season. Wild gardens bloom like paintings beyond each window, mature trees stand guard, and you may spot a neighborhood cat sunning itself in the afternoon. Mornings begin with a chorus of birdsong drifting through the windows; evenings are for sunsets from the porch, the living room, dining room, the tiny “Rapunzel Room” arched window or from the front door. 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. Cheers, -Your Cottage Keepers Guest access During your stay, you’ll have full, private access to the 12 rooms of The Pleasant Hill Cottage, every nook thoughtfully designed for comfort, charm, and a touch of magic: *Living Room – Sunlight pours in through large windows framed by mature greenery, offering a cozy retreat for conversation, reading, or simply gazing out at nature. *Dining Room – Perfect for shared meals, board games, or a cup of tea in the afternoon glow. *Kitchen – Fully equipped and thoughtfully stocked with both essentials and a few extras to inspire your inner chef. *3.5 Guest Rooms – Three full bedrooms, plus a charming attached sleeping room ideal for children or extra guests. *2.5 Bathrooms – Beautifully updated with modern comforts, luxury soaps, shampoos, conditioners, blow dryers, Q-tips, non-slip shower mats, and 100% cotton bath linens. *Basement Bonus Room – A versatile space for movies, games, or simply relaxing. *Designated Workspace – An inspiring corner for those working remotely. *Laundry Room – Washer, dryer, laundry orgizning drawers, iron & ironing board, steamer, and laundry supplies. Outdoor Spaces: *Front porch *Front yard *Back patio *Backyard *South side yard ***Kind Note: The shed and north side yard are reserved for owner storage only, please do not go in these areas. *Parking – On-site parking for 2 small to medium vehicles in the driveway, with easy street parking available for more. Please let us know if you'll be bringing more than 2 vehicles so we can make arrangements for you. Amenities & Extras For Families: *Travel crib (Pack ’n Play) with fresh organic cotton linens - available for you to use if you need it *Baby bath hammock - available for you to use if you need it *Highchair - available for you to use if you need it *Baby gates for safety - available for you to use if you need them *Kids’ books & reading nooks with floor cushions *Kids’ indoor lanterns in reading nooks *Toys, drawing pads, and games (sanitized between stays) Outdoor Fun: *Beach toys, football, volleyball, basketball, frisbee cornhole, bocce ball, tennis rackets, pickleball paddles *Hammock & sun loungers *Six rocking chairs *Bistro tables (front porch & back patio) *Firepit with s’mores sticks *Flat-top griddle grill *Solar-lit landscaping and stair lights Entertainment: *Bluetooth speaker *x4 Tv's *Books displayed throughout *World globes & educational décor *Board games, card games, and puzzles *Beach gear (including beach towels) Comfort & Wellness: -Plush throw blankets in every room, freshly laundered -100% cotton bed linens -Pillow options in each bedroom -Non-toxic cleaning & laundry products -Essential oil peppermint spray for bugs or refreshing rooms -Clay-based paint on all walls & trim throughout the cottage, for a healthier environment -Small hand weights for a quick workout -Charging station plugs in each room for USB, USB-C, and standard plug cords that you bring -Spa service recommendations & at-home booking options in the Welcome Book -Seasonal cold plunge opportunities at nearby beaches -All guests are required to take their shoes off at the door, to keep the home fresh, clean, and welcoming for every guest -Smoke & Carbon monoxide alarms on each level of the cottage Kitchen & Dining: *Fully stocked cookware, utensils, and baking essentials *Toaster oven, small blender, tea kettle, French press, & manual juicer *Olive oil, salt, pepper, & toothpicks provided *Fire blanket (in cabinet to the right of the stove) Other things to note Upon your arrival, you’ll discover a beautifully organized and beyond detailed Welcome Book, thoughtfully prepared to guide you through the cottage, it's grounds, the charming town and beyond. Within its pages are not just directions and tips for a seamless stay, but also our favorite hidden gems, local treasures, and little sparks of inspiration to make your visit truly unforgettable... like a trusted friend sharing their best-kept secrets to help you enjoy every moment of your stay with ease. We’ve also curated a thoughtful collection of local, surrounding, and Chicago-area recommendations, including: *Restaurants featuring global cuisine - with a few of our personal menu favorites * Our favorite breathtaking beaches nearby and the best times to visit *Charming lakeside towns worth exploring along Lake Michigan - including Lake Bluff, Lake Forest, Highwood, Highland Park, Glencoe, and Winnetka (yes, the town where the movie Home Alone was filmed!) *Parks, forest preserves, and scenic trails we love to walk or bike *Coffee shops we love for a morning stroll or afternoon pick-me-up *Ravinia - Just minutes away, the legendary Ravinia Festival invites you to sip champagne under the stars as world-class performers take the stage. Pack a gourmet picnic or indulge in on-site fine dining, and experience music as it was meant to be - surrounded by candlelight, lush gardens, and the magic of a summer night on the North Shore. Unforgetable! *Chicago Botanic Garden - Just minutes away... Lose yourself in 385 acres of pure floral wonder at the Chicago Botanic Garden, where 27 enchanting gardens and four natural habitats bloom in every season. From serene Japanese gardens to dazzling rose displays, every path invites awe, beauty, and inspiration. *Train routes & Metra stops - perfect for easy day trips into downtown Chicago *Chicago Bears Training Camp - tips for fans hoping to catch a glimpse of the action. *Great Lakes Naval Training Facility - from one soldier to another, we deeply appreciate your service and dedication to keeping our great country & freedoms secure. Thanking you isn't big enough. Home to the U.S. Navy’s only boot camp, the Great Lakes Naval Station offers a proud glimpse into American maritime tradition. Families visiting graduating sailors will find our cottage the perfect nearby retreat - warm, comfortable, and just minutes from the your cherished solider. *Local festival calendar — featuring events here in town and in Lake Bluff, Lake Forest, Highland Park, Glencoe, Winnetka, and beyond. *Six Flags - for all you thrill seekers! *Outdoor Activities - including water, nature & sports *THE BEST PIZZA spots around (we take this very seriously!) *Spas & wellness spots nearby and our favorites in Chicago - including how to book services that come right to the cottage. *Boutique shopping districts in the surrounding towns filled with hidden gems. *Art galleries, museums, and cultural attractions both local and in the city *Live music venues, wine bars, and local breweries for a memorable night out *Staying In: Cozy Days & Relaxing Nights... Not every day needs an itinerary. For those slower-paced moments, your manual includes a collection of our favorite ways to unwind right here at the cottage. Whether it’s a slow morning with coffee or a candlelit evening by the fireplace, we’ve got you covered. Want to Pre-Book Something Before You Arrive? We’re happy to help if ample time is provided and if we're able! Whether you're dreaming of a spa day, craving a specific dish, booking a concert, or planning a special outing, just reach out. We’ll work with you and send you curated options ahead of your arrival. Whether you’re here to unwind, explore, or indulge, your guide is designed to help you settle in like a local and make the most of every moment of your stay here. We take great pride in offering impeccable, insider recommendations, the kind we’d share with our dearest family and friends. With decades of experience living throughout Chicago and the North Shore, we’re excited to help you explore the very best the area has to offer. We would be beyond thrilled to host you! Happy Travels! :) — The Pleasant Hill Cottage Team