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The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

Family-friendly stay near Lake Michigan

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Fridge, oven, stovetop, dishwasher
Smart TV, fireplace, books, stereo
Property grounds
Exterior
Property grounds

Entire home

3 bedrooms3 bathrooms1650 sq ft

Popular amenities

  • Outdoor Space
  • Barbecue grill
  • Kitchen
  • Fireplace
  • Washer
  • Dryer

Explore the area

View in a map
Highwood, IL
  • Chicago Botanic Garden
    ‪7 min drive‬
  • Lake Forest College
    ‪9 min drive‬
  • Naval Base Great Lakes
    ‪18 min drive‬
  • Chicago, IL (PWK-Chicago Executive)
    ‪19 min drive‬

Room options

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About the neighborhood

Highwood

In Highwood .You'll find Lake Michigan and Moraine Park within 2 miles (3 km) of this cottage. Highland Park Ambulatory Care Center and Park Avenue Boating-Fishing Beach are also within 2 miles (3 km).

What's nearby

  • Ravinia Park - 7 min drive - 4.2 miles
  • Chicago Botanic Garden - 7 min drive - 5.7 miles
  • Ravinia Pavilion - 8 min drive - 4.4 miles
  • Lake Forest College - 9 min drive - 4.8 miles
  • Naval Base Great Lakes - 18 min drive - 9.6 miles

Getting around

  • Highwood Station - 12 min walk
  • Chicago, IL (PWK-Chicago Executive) - 24 min drive

Restaurants

  • ‪Starbucks at NorthShore Highland Park Hospital - ‬3 min drive
  • ‪Starbucks - ‬4 min drive
  • ‪28 Mile Vodka Company - ‬15 min walk
  • ‪La Plancha Loca - ‬17 min walk
  • ‪Wooden Nickel - ‬16 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

Similar properties

Property amenities

Beach

  • Beach towels

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Family friendly

  • Children's books
  • Children's dinnerware
  • Children's games
  • Children's toys
  • High chair
  • Stair gate
  • Travel crib

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Lobster/crab pot
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • 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

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 elevator
  • Tile flooring in public areas
  • Well-lit path to entrance

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

Contactless check-in available

Check-out

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.
Failure to complete these may result in a negative review from the host.

Children and extra beds

  • Children are welcome.

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 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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 uses eco-friendly cleaning products. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Frequently asked questions

How close is The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! to the airport?

This cottage is 13.4 mi (24-min drive) away from the Chicago, IL (PWK-Chicago Executive) airport, the closest popular airport to the property.

Does The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! to the beach?

This cottage is 2 mi (8-min drive) from Park Avenue Boating-Fishing Beach and 3.6 mi (13-min drive) from Rosewood Beach. Don't forget your sunscreen!

Does The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!?

No, there is no casino at this cottage, but The Temporary by American Place (19-min drive) is nearby.

Is there free parking at The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!?

Free parking is not available at this cottage.

Does The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! have a pool?

This cottage does not have a pool.

Does The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! have a spa?

There are no spa services available at this cottage.

How close is The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! to downtown Highwood?

This cottage is 0.6 mi away from Highwood.

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