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.The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining

Photo gallery for .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining

A stone house with a dark blue door, a metal staircase, and a star-shaped light fixture above the door.
A dining area with a white table set with glassware and plates, a gold-rimmed lamp, and a white cabinet with silver bowls.
A stone house with a triangular roof, surrounded by a well-maintained garden with various shrubs and a small tree.
A cozy living room with a fireplace, comfortable seating, and large windows.
A modern kitchen with white cabinetry, a stainless steel range hood, and a window with blue-tiled frames.

Reviews

10 out of 10
Exceptional

Highlights

  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Discover nearby landmarks
    Close to Lake Michigan
3 bedrooms2+ bathroomsSleeps 10

Popular amenities

  • Patio
  • Toys
  • Dog-friendly
  • On-site fitness centre
  • Barbecue grill
  • Air-conditioning

Explore the area

View in a map
Highwood, IL
  • Place, Moraine Park
    ‪18 min walk‬
  • Place, Naval Base Great Lakes
    ‪20 min drive‬
  • Place, Six Flags Great America
    ‪31 min drive‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪43 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. North Shore Beaches Ravinia Weddings Families Dining

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

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Not childproofed - please mind & store breakables.
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Events

No events allowed
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Pets

Pets allowed: dogs less than 9 kg per pet (limit 2 pets total)
Pets welcome 2 max; disclose before booking. Fees.
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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.
We kindly ask that you remove your shoes when in the cottage. Thank you!
We Kindly ask that you only put toilet paper down the toilet, nothing else please. The cottage has an old system and is very sensitive. Thank you!
Please don't put suitcases or bags on the beds, we have all white linens. We have multiple luggage racks in each room, please use them. Thank you!

Important information

You need to know

Property # 4752161vb
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
Long-term renters welcome
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

About the area

Highwood

Located in Highwood, this cottage is near theme parks and near a water park. 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 Northbrook Sports Complex, or check out an event or a game at Welsh-Ryan Arena. Take in the nearby slopes with cross-country skiing, or try out other outdoor activities such as ice skating.
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Map
Highwood, IL

What's nearby

  • Moraine Park - 18 min walk - 1.5 km
  • Naval Base Great Lakes - 20 min drive - 16.9 km
  • Northwestern University - 25 min drive - 21.8 km
  • Six Flags Great America - 31 min drive - 28.1 km
  • Donald E. Stephens Convention Center - 40 min drive - 40.9 km

Getting around

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

Restaurants

  • ‪NorthShore Highland Park Hospital - ‬3 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Tala Coffee Roasters - ‬12 min walk
  • ‪Starbucks - ‬4 min drive

Frequently asked questions

Is .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 9 kg per pet.

How much does it cost to stay at .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining?

As of 11 Oct, 2026, prices found for a 1-night stay for 2 adults at .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining on 12 Oct, 2026 start from S$2,659, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining?

On-site parking is available at the property.

What time is check-in at .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining?

Check-in begins at 3:00 PM.

What time is check-out at .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining?

Checkout is at 11:00 AM.

Where is .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining located?

This family-friendly Highwood cottage is within 2 mi (3 km) of Lake Michigan and Highland Park Ambulatory Care Center. Rosewood Beach and Forest Park Beach are also within 6 miles (10 km). Highwood Station is 12 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

9.6/10

Check-in

10/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this cottage. The property was absolutely immaculate, and the host was incredibly responsive and communicated everything very clearly throughout our visit.The cottage itself is beautiful and located in a quiet, peaceful neighborhood, which made it a great place to relax after a busy day. We also really appreciated the thoughtful touch of the complimentary cupcakes—they were delicious!Everything about our stay was comfortable, welcoming, and well cared for. We would absolutely stay here again and highly recommend it to anyone visiting the area.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely AMAZING house, host, and neighborhood. We let Terri know we were celebrating and we arrived to the house decorated special just for us- so incredibly thoughtful. Everything was so above and beyond, and the house has everything you could possibly need and more. I can't wait to stay here again some time! Pleasant, whimsical & perfect!!
Stayed 2 nights in May 2026
Response from VrboOwner on 17 May, 2026
Awww! Emma! 🥹🫶✨️ ...your review absolutely made our hearts glow!!! 🥹💖✨ Thank you so much for your beyond kind words. 🫶 It truly means the world to us that you & your lovely friends chose to celebrate such a beautiful chapter of your life here at The Pleasant Hill Cottage. 🥂✨🎈💍 We’re so happy the little touches & whimsy of the cottage made your weekend feel extra special! 🩷🥂✨ It’s always our honor & goal to create meaningful stays filled with warmth, beauty & unforgettable moments. 🧚‍♀️✨🏡💐 You were an absolute joy to host, and we would welcome you back with open arms anytime!!! 🫶☺️✨ Wishing you so much happiness & beautiful adventures ahead in this next exciting season of life! 💖🥂✨ Cheers! 🥂 with warmth & gratitude, ✨ -🧚‍♀️Terri & The Pleasant Hill Cottage Team🪄
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved our stay at Pleasant Hill Cottage! The home is so inviting, cozy, and comfortable, and you can immediately tell how much thoughtful care the owners have put into every detail. There were so many wonderful amenities and little touches throughout the cottage that made it truly feel like a home away from home.The location was great, the house was beautifully decorated and well-equipped, and everything about our stay exceeded our expectations. Terri was an incredibly gracious and welcoming host and made sure we had everything we needed.We’ve stayed at many vacation rentals over the years, and Pleasant Hill Cottage is truly one of our favorites. We would absolutely stay here again and highly recommend it!
Stayed 5 nights in Aug 2026
Response from VrboOwner on 17 Aug, 2026
Kathryn…🥹🩷✨ Thank you from the bottom of our hearts for this absolutely beautiful review!💗 Reading that The Pleasant Hill Cottage has become one of your favorite vacation rentals after so many stays elsewhere is truly one of the greatest compliments we could ever receive!🥹🫶✨ We loved having you and your family here, and knowing the cottage felt every bit as cozy, welcoming & special as we hoped it would makes us smile SO big!💗 Thank you for noticing all the tiny details, for appreciating the heart behind them, and especially for being such wonderful guests!💗 We feel incredibly lucky when lovely guests like you find their way to our sweet little pocket of the North Shore. 🧚🏼‍♀️💗🏡☕️💐✨ Our cottage door will always be happily waiting to welcome you back anytime...🌷🏡✨ ...to add another happy chapter to her endless tale. 🏡🗝️📖💗✨ with warmth & heartfelt gratitude,✨ 🧚‍♀️Terri & The Pleasant Hill Cottage Team🪄
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous home! Loved the decor and all the special touches. Very generous host. We adored our time here and highly recommend.
Stayed 2 nights in Aug 2026
Response from VrboOwner on 4 Aug, 2026
Aw, Elena... 💗 Thank you so much for taking the time to leave us such a beautiful 5-star review! 💗 It truly means the world to us! 💗 Reading that you loved our cottage & adored your time here is one of the greatest compliments we could ever receive! 💗 Thank you so much for making our day with your incredibly kind words! 💗 It was such a joy to host you & your family!💗 We hope whenever life brings you back to the North Shore, you'll know that you always have a cozy little cottage waiting to welcome you back.💗 Thank you again for staying with us!💗 Have a lovely summer ahead! ☀️ with warmth & heartfelt gratitude, ✨️🧚‍♀️Terri & The Pleasant Hill Cottage Team

About the host

Hosted by Terri

Host profile image
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.✨

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 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. ♡

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