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

Q: How much does it cost per night to stay in Highwood cottage?

Best-rates for the Highwood cottage starts from $1,014 per night with includes Security/Safety, Sports/Activities, Bedding/Linens, Ocean View, Balcony/Terrace, Wellness Facilities, Barbecue/Outdoor Cooking, Child Friendly, Entertainment, Air Conditioner, View, Fireplace/Heating, Guest Services, Internet, Kitchen, Laundry, Parking, TV with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

New | 3 Bedrooms 2 Bathrooms 10 Guests

New Listing

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

3 Bedroom Cottage in Highwood

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

The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! is located in Highwood. The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! provides accommodation, featuring Balcony/Terrace, Wellness Facilities, Barbecue/Outdoor Cooking, among other amenities. This Cottage features Balcony/Terrace, Wellness Facilities, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! has 3 Bedrooms , 2 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Highwood has interesting places to visit. If you want to learn more about the Cottage in Highwood, such as places to visit and things to do nearby, you can check below to learn more.

Amenities

Air Conditioner
Parking
TV
View
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Policies

Event Policy No events allowed

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

Child Policy Children are welcome. note from host: not childproofed - please mind & store breakables.

Pet Policy Pets not allowed

Smoking Policy Smoking is not permitted

Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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 this property uses eco-friendly cleaning products

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FAQ's

Is this Highwood cottage pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Highwood cottage have a swimming pool?

No, this Highwood cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Highwood cottage?

Best-rates for the Highwood cottage starts from $1,014 per night with includes Security/Safety, Sports/Activities, Bedding/Linens, Ocean View, Balcony/Terrace, Wellness Facilities, Barbecue/Outdoor Cooking, Child Friendly, Entertainment, Air Conditioner, View, Fireplace/Heating, Guest Services, Internet, Kitchen, Laundry, Parking, TV with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Highwood cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Highwood cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Highwood cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Highwood cottage?

Based on the information reported by the owner or manager, the Highwood cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Highwood cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the Highwood cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check Cottage Availability

Nightly rates from:

US $1,014