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!





Entire home
3 bedrooms3 bathrooms153 sq m
Popular amenities
- Outdoor space
- Barbecue grill
- Kitchen
- Fireplace
- Washer
- Dryer
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
Room options
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About the area
Highwood
With a stay at this cottage in Highwood, you'll be within a 5-minute drive of Lake Michigan and Moraine Park. .This family-friendly cottage is 9.4 mi (15.1 km) from Naval Base Great Lakes and 14.2 mi (22.8 km) from Northwestern University.
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
- Highwood Station - 12 min walk
- Chicago, IL (PWK-Chicago Executive) - 24 min drive
Restaurants
- NorthShore Highland Park Hospital
- Starbucks at NorthShore Highland Park Hospital - 3 min drive
- 28 Mile Vodka Company - 15 min walk
- Wooden Nickel - 16 min walk
- Tala Coffee Roasters - 12 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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
Make yourself comfortable in this air-conditioned cottage, which features a fireplace and a Smart TV. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Enjoy recreation amenities such as a fitness center or take in the view from a garden.
Guests will find features like internet access and onsite parking.
Property amenities
Beach
- Beach towels
Internet
- Available in the cottage: Free WiFi
Parking and transport
- Parking on site
Kitchen
- Blender
- Coffee grinder
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Electric kettle
- Hob
- Lobster/crab pot
- Oven
- Paper towels
- Refrigerator
- Spices
- Toaster
Dining
- Dining table
Bedrooms
- 3 bedrooms
- Bedsheets provided
Bathroom
- 2.5 bathrooms
- Bathtub or shower
- Hair dryer
- Shampoo
- Soap
- Toilet paper
- Towels provided
Living spaces
- Dining table
- Fireplace
- Separate dining area
Entertainment
- Books
- Games
- Smart TV with cable/satellite channels
- Stereo
Outdoor areas
- Barbecue grill
- Firepit
- Garden
- Outdoor furniture
- Patio
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Computer monitor
- Desk
- Desk chair
Comfort
- Air conditioning
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
- 12 steps to reach entrance
- Area rugs in public areas
- Cobblestone flooring in public areas
- Hardwood flooring in public areas
- No lift
- Tile flooring in public areas
- Well-lit path to entrance
- Smoke-free property
Services and conveniences
- Iron/ironing board
Location highlights
- Near a health/beauty spa
- Near a hospital
- Near the marina
Things to do
- Gym
- Basketball nearby
- Birdwatching nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Ice skating nearby
- Jet skiing nearby
- Kayaking nearby
- Motor boating nearby
- Sailing nearby
- Swimming nearby
- Water tubing nearby
- Wildlife walks nearby
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- First aid kit
- Fire extinguisher
- Deadbolt lock
General
- At least 80% lighting from LEDs
- Eco-friendly cleaning products used
- Energy-saving switches in guestrooms
- Garden
- Recycling
- Unit size: 1,650 square feet
- Water-efficient toilets
Policies
Check-in
Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 21
Check-out
Check-out before 11:00 AM
Contactless check-out available
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Check-out instructions
The host requires you complete the following before checking out:
Load the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
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.
Pets
Pets not allowed
Children and extra beds
Children are welcome
Note from host: Not childproofed - please mind & store breakables.
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
Onsite parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
This property does not have elevators
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