Entire home
The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
Photo gallery for The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!





3 bedrooms 2+ bathrooms 153.3 sq m
Popular amenities
Explore the area
Highwood, IL
- Chicago Botanic Garden7 min drive
- Lake Forest College9 min drive
- Naval Base Great Lakes18 min drive
- Chicago, IL (PWK-Chicago Executive)19 min drive
Rooms & beds
3 bedrooms
*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 and 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.
The Pleasant Hill Cottage unfolds across three levels, with three bedrooms (including a quaint attached sleeping 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 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 from the porch, the living and dining rooms, the tiny “Rapunzel Room” arched window, & through 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 strong...
with warmth,
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 and 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.
The Pleasant Hill Cottage unfolds across three levels, with three bedrooms (including a quaint attached sleeping 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 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 from the porch, the living and dining rooms, the tiny “Rapunzel Room” arched window, & through 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 strong...
with warmth,
Your Cottage Keepers
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Gym
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House Rules
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
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
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
We should mention
This property does not have any lifts
About the area
Highwood
Highwood is home to this cottage. The area's natural beauty can be seen at Lake Michigan and Kent Fuller Air Station Prairie, while Ravinia Park and Ravinia Pavilion are cultural highlights. Travelling with kids? Consider Northbrook Sports Complex, 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
- Ravinia Park - 7 min drive - 6.7 km
- Chicago Botanic Garden - 7 min drive - 9.2 km
- Ravinia Pavilion - 8 min drive - 7.1 km
- Lake Forest College - 9 min drive - 7.7 km
- Naval Base Great Lakes - 18 min drive - 15.4 km
Getting around
Restaurants
- Starbucks at NorthShore Highland Park Hospital - 3 min drive
- 28 Mile Vodka Company - 15 min walk
- La Plancha Loca - 17 min walk
- Wooden Nickel - 16 min walk
- Denny's - 4 min drive
Frequently asked questions
Reviews
Reviews
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About the host
Hosted by Terri

Languages:
English
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