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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 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.
A mirror with a decorative frame, a wooden dresser, and a vase with flowers.
A dining area with a white table set with glassware and plates, a gold-rimmed lamp, and a white cabinet with silver bowls.

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

Popular amenities

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

Explore the area

View map
Highwood, IL
  • Place, Moraine Park
    ‪18 min walk‬
  • Place, Naval Base Great Lakes
    ‪22 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

Add dates for prices

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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 Par-King Skill Golf, 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 - 22 min drive - 18.6 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 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 August 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 August 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
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