Entire home
The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
Family-friendly cottage with water park and fitness centre
Photo gallery for The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
3 bedrooms2+ bathroomsSleeps 101650 sq ft
Popular amenities
Explore the area
Highwood, IL
- Place, Highland Park Ambulatory Care Center11 min walk
- Place, Highland Park Country Club4 min drive
- Place, Park Avenue Boating-Fishing Beach4 min drive
- Airport, Chicago, IL (PWK-Chicago Executive)18 min drive
Rooms & beds
3 bedrooms (sleeps 10)
*The Gilded Lily Suite*
1 Queen Bed
*The Revived Relic Suite*
2 Double Beds
*The Storybook Suite*
1 King Bed and 2 Single Beds
2 bathrooms, 1 half bathroom
*Powder Room*
Towels provided · Toilet
*Washroom I*
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
*Washroom II*
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden
Dining area
About this property
The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
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
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
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Gym
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House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Not childproofed - please mind & store breakables.
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Please close all windows.
Please place used towel in bathtubs.
Belongings unclaimed will be donated after 7 days.
Failure to complete these may result in a negative review from the host.
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
We should mention
This property does not have any lifts
About the area
Highwood
Located in Highwood, this cottage is near theme parks. The area's natural beauty can be seen at Lake Michigan and Middlefork Savanna Forest Preserve, while Ravinia Park and Ravinia Pavilion are cultural highlights. Travelling with kids? Consider Par-King Skill Golf, or check out an event or a game at Welsh-Ryan Arena. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Highwood, IL
What's nearby
- Highland Park Ambulatory Care Center - 11 min walk - 1.0 km
- Moraine Park - 18 min walk - 1.5 km
- Highland Park Country Club - 4 min drive - 2.9 km
- Park Avenue Boating-Fishing Beach - 4 min drive - 2.5 km
- Naval Base Great Lakes - 16 min drive - 19.0 km
Getting around
Restaurants
- NorthShore Highland Park Hospital - 3 min drive
- 28 Mile Vodka Company - 15 min walk
- Starbucks at NorthShore Highland Park Hospital - 3 min drive
- Tala Coffee Roasters - 12 min walk
- Wooden Nickel - 16 min walk
Frequently asked questions
About the host
Hosted by Terri
Greetings!✨️
A nickname my family & friends gave me long ago "Fairy Terri"✨️ a name born from a passion of turning the simplest moments into something magical & full of wonder.✨️ It’s how I move through the world.✨️
Being able to welcome guests from so many corners of the world & sprinkle a little magic near & far is such a dream & honor. I’m forever grateful for the chance to be a small part of our guests’ stories & them a small part of ours.✨
A nickname my family & friends gave me long ago "Fairy Terri"✨️ a name born from a passion of turning the simplest moments into something magical & full of wonder.✨️ It’s how I move through the world.✨️
Being able to welcome guests from so many corners of the world & sprinkle a little magic near & far is such a dream & honor. I’m forever grateful for the chance to be a small part of our guests’ stories & them a small part of ours.✨
Why they chose this property
A quiet little village tucked into Chicago’s North Shore, Highwood is one of those rare places that feels both alive and at peace all at once. The town dances with live music, world-class restaurants, and a colorful lineup of festivals that fill the streets with laughter and light all year long. Perched right on top of Lake Michigan, Highwood has become the heartbeat of the North Shore, where locals and all the neighboring towns gather for incredible dining, vibrant nightlife, and community events that truly celebrate the art of living well.
What makes Highwood special, though, isn’t just its energy, it’s the people. It’s the kind of town where neighbors wave, small business owners know your name, and every corner has a story. Just beyond the lively downtown, our street rests in a peaceful pocket of town that borders the beautiful Exmoor Country Club Golf Course. It’s a charmingly quiet block, wrapped in old trees and golden light, where you can hear the crickets and the sway of the trees at night.
From our doorstep, you can stroll to the lake, explore scenic nature preserves, or wander into town for brunch, coffee, live music, or handmade pasta under twinkling lights. Whether you’re here to unwind or explore, Highwood has a way of making you feel instantly at home, an incredible little world where small-town charm meets the culture and elegance of Chicago’s North Shore. ♡
What makes Highwood special, though, isn’t just its energy, it’s the people. It’s the kind of town where neighbors wave, small business owners know your name, and every corner has a story. Just beyond the lively downtown, our street rests in a peaceful pocket of town that borders the beautiful Exmoor Country Club Golf Course. It’s a charmingly quiet block, wrapped in old trees and golden light, where you can hear the crickets and the sway of the trees at night.
From our doorstep, you can stroll to the lake, explore scenic nature preserves, or wander into town for brunch, coffee, live music, or handmade pasta under twinkling lights. Whether you’re here to unwind or explore, Highwood has a way of making you feel instantly at home, an incredible little world where small-town charm meets the culture and elegance of Chicago’s North Shore. ♡
What makes this property unique
Every home has a story, but ours feels like it was written in a fairytale. Perched on a gentle hill in the heart of Highwood’s historic cottages, our cottage is both timeless and thoughtfully reimagined, blending old-world charm with updated conveniences. From the moment you arrive, the feeling is hard to describe… sunlight filters through her oversized window panes, music may hum sofly from a sweet italian neighbor, and every corner seems to hold a touch of warmth and magic.
We’ve poured our hearts into every detail, from the curated antiques and designer furnishings to the custom artwork, linens, and lighting that make each room glow uniquely its own. The kitchen, wrapped in spa-blue herringbone tile and gleaming silvers, was designed to inspire lingering breakfasts and late-night laughter. Upstairs, the Rapunzel Room feels like something straight out of a storybook, while the Storybook, Gilded Lily and Revived Relic Suites each offer their own sense of charm and nostalgia.
Outside, boxwood-lined stairs, gardens, rocking chairs, and a bonfire invite guests to slow down and breathe. The cottage is surrounded by mature trees and peaceful walking paths and sidewalks that lead to Lake Michigan, forest preserves and town. We’ve created spaces meant for connection... bridal parties preparing for their big day, families reuniting by the fire, and travelers seeking a bit of calm between adventures.
What truly makes the cottage unique isn’t just its design, but the feeling it gives. Guests often tell us it feels “alive”... as if the walls have witnessed countless happy memories and are ready to hold yours, too. It’s a place that reminds people how good it feels to belong, to rest, and to be surrounded by beauty made with love. ♡
We’ve poured our hearts into every detail, from the curated antiques and designer furnishings to the custom artwork, linens, and lighting that make each room glow uniquely its own. The kitchen, wrapped in spa-blue herringbone tile and gleaming silvers, was designed to inspire lingering breakfasts and late-night laughter. Upstairs, the Rapunzel Room feels like something straight out of a storybook, while the Storybook, Gilded Lily and Revived Relic Suites each offer their own sense of charm and nostalgia.
Outside, boxwood-lined stairs, gardens, rocking chairs, and a bonfire invite guests to slow down and breathe. The cottage is surrounded by mature trees and peaceful walking paths and sidewalks that lead to Lake Michigan, forest preserves and town. We’ve created spaces meant for connection... bridal parties preparing for their big day, families reuniting by the fire, and travelers seeking a bit of calm between adventures.
What truly makes the cottage unique isn’t just its design, but the feeling it gives. Guests often tell us it feels “alive”... as if the walls have witnessed countless happy memories and are ready to hold yours, too. It’s a place that reminds people how good it feels to belong, to rest, and to be surrounded by beauty made with love. ♡
Languages:
English
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