Top 5 Airbnb Vacation Rentals In Highland Park, Illinois - Updated 2021

airbnb highland park

You probably heard of Highland Park because it hosts the famous Ravinia Music Festival. This music festival is the oldest among all music festivals in the country and stages the widest range of artists from different music genres. This city is also renowned for its architectural marvels by notable architects such as Frank Lloyd Wright, John S. Van Bergen, and David Adler whose works are listed in the National Register of Historic Places. To add, nature enthusiasts will love trailing and biking around the parks, gardens, and preserves which are covered in unadulterated land and water bodies. More so, family vacationers are always welcome to have a good time in the city’s pristine beaches. To have a full experience of the city’s posh lifestyle, check out the following Airbnb vacation rentals in Highland Park, Illinois.

1. Classy private home with a pool (from USD 420)

Continue to live a luxurious life even when you are on vacation as you stay in this beautiful 2-acre (0.8 hectares) property located in one of the city’s areas with architectural treasures. Every part of the house is spacious, bright, and decorated with minimalist décor that adds to the house’s sophistication. You can prepare your family’s feast with ease in the full kitchen. Also, your family can have fun bonding moments in the basement with a fireplace. Outside, you can see the vast private backyard and the heated pool which is opened during summer. The house is near Ravinia and botanical gardens. The other amenities include WiFi, cable TV, heating system, air conditioning, essentials, and four bathrooms, one of which has a tub.

Safe private retreat on two acres with heated pool
Highland Park, Illinois, United States
43 reviews
Entire house 6 Beds 6 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
with 6 bedrooms and 4 bathrooms it easily accommodated our family
first the good stuff:the beds were really comfortable and the furniture inside was really nice and well decorated
gorgeous stylish home plenty of room for our group of 8
we were immediately impressed with the size and beautiful decor and gourmet well stocked kitchen
highly recommended clean great bbq grill great pool lots of house space beautiful property
this was an amazing clean relaxing place to stay
beautiful spacious and spotlessly clean home in an excellent location
home is very clean and spacious
the place was very clean and had all of the necessities for a few nights stay
the house was wonderful just as described it was very neat and clean and had welcoming touches
kailash was an outstanding host
amazing stay very thoughtful host
the host was amazing checked on us during our stay to make sure we didn’t need anything
kailash is a wonderful host this was by far my best airbnb experience
this place was beyond gorgeous and kailash was very helpful and responsive he even stopped by to assist us
beautiful area/ trails for walking and running nice trails close to house
great place and perfect location and distance from navy yard and airport
the neighborhood is quiet and is in a perfect location
great house for families great location
fantastic location close to restaurants shopping great lakes navy base and so much more
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2. Exquisite four-bedroom retreat (from USD 385)

Take a breather and relax with your family in this spacious zen house. The interior of this home is well-lit thanks to floor-to-ceiling windows which enable natural lighting from the outside to flood in. There are splashes of colors here and there and natural touches throughout this lovely home. The kitchen is immaculate. You can cook your family’s favorite dishes without a hassle on days when you all prefer to not dine out at the nearby restaurants. There is an outdoor patio with comfortable seating, perfect for early morning coffee sips and afternoon book indulgences. The amenities include air hockey in the basement, WiFi, a cable TV, an indoor fireplace, air conditioning, heating, baby needs, a bathtub, essentials, an outdoor barbecue grill, and free parking on the premises.

Rejuvenate and Relax in the North Shore
Highland Park, Illinois, United States
49 reviews
Entire house 7 Beds 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the kids liked the air hockey and tv in the downstairs area
all beds were comfortable and we lacked for nothing as far as supplies and amenities
the beds are very comfortable and the linen closet is well stocked
the beds are comfortable and the linens are high quality
my family loved all the rooms with beautiful bedding
it is extremely clean and thoughtfully decorated
the house is spacious well stocked and clean
the place was clean spacious and in a good location
comfy clean well located good communication
the hallway closet upstairs was packed full of clean towels
the hosts were very helpful
lana and luca are great hosts
communicative and courteous host
they were quick and responsive when we had questions
lana and luca were great hosts very responsive to all our questions before and during our stay
it is an easy walk to very good restaurants
this is a wonderful property in a great location
the location was perfect for our needs and the house was too
the house is in a very nice area and centrally located within highland park
we found this house to be a nice place to stay in highland park
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3. Room in a homey oasis nestled on a quiet residential street (from USD 48)

This 1920s house is located near restaurants and shops so you can eat and dine as you wish with ease. The room you will be renting has two comfortable beds and can fit two people quite well. It is also only a short walking distance to Lake Michigan where you can take peaceful afternoon walks. Moraine Beach is also nearby. More so, the train station is only a short drive away so you can visit Chicago during your stay here. You will be sharing the rest of the house with the very accommodating owners, but it will not be a problem because your comfort is their top priority. The amenities they offer include WiFi, heating, essentials, and free parking.

Highland Park Oasis
Highland Park, Illinois, United States
128 reviews
Private room in house 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
i also enjoyed the amish rocking chair in my room next to a little reading lamp
it's quiet in the evenings and the bed was very comfortable - perfect for a good nights' rest
my stay with her was incredibly comfortable and restful
the two beds make it a perfect spot for a friends trip
the room was clean cozy and quiet
room was clean with plenty of space
there is a shared bathroom - comfortable and clean
the bedroom was quaint clean and comfortable
the room was so clean and smelled fresh and the bed was comfy
the host was amazing
thank you for being a great host
marjorie is a great host
marjorie was very responsive
marjorie is a very gracious host
great location and affordable price
good location for work
wonderful location for those getting away from the hustle and bustle
this is a great location in highland park
great location good value for money
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4. Elegant yet comfortable historic chateau (from USD 265)

You will feel like living in a museum when you rent this ritzy home called Le Petite Chateau because various paintings are displayed throughout the house. The house itself is even a work of art. Built in 1932, this splendid home has been renovated for it to be livable and cozy. Its authentic architecture has been restored to retain the house’s original charm and splendor. Your comfort is never compromised when you stay in this unique home. The rooms are tidy and elegantly styled. You may choose to cook in their fully equipped kitchen or to dine out in the nearby restaurants. Even the yard is beautifully maintained. WiFi, TV, heating, air conditioning, an indoor fireplace, essentials, and free parking on the premises are also provided.

Le Petite Chateau
Highland Park, Illinois, United States
18 reviews
Entire house 2 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
clean and restful in a quiet setting
spotless super cozy neat and stylish
hosts were great
the home is lovely a restored treasure in highland park accommodations wonderful hosts superb and attentive
jeff and john are fantastic hosts we will return
jeff was a wonderful host and the home was beautiful and sparkling clean
thanks to jeff for being a wonderful and responsive host
ideal location and only a 40minute train to downtown
the location is beautiful and close to downtown highland park for restaurants and shopping
close proximity to ravina festival grounds the lake and a water park
great upscale neighborhood walking distance to grocery quaint downtown
we felt safe and comfortable our whole stay and it was in a great location
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5. Comfy, private two-bedroom suite on the second floor of a home

The perfect place to stay when you go on a vacation is somewhere centrally located because you can go to as many places as you want. Whether it be fancy restaurants or quick eateries, shopping districts, botanical parks, North Shore beaches, Ravinia, or even downtown Chicago, you can reach all of these places when you rent this two-bedroom suite with a bath in the second floor of a lovely home surrounded by lush shrubs and flowering plants. The rooms are spic and span and comfortable to ensure that you will have a good night’s sleep. In the morning, enjoy a nourishing breakfast served by your hospitable hosts. You may also share with the hosts their well-equipped kitchen and outdoor patio. Other amenities include WiFi, cable TV, heating, air conditioning, essentials, desktop computer with internet, and free parking.

Private Two Bedroom Suite Walk to Food & Fun
Highland Park, Illinois, United States
32 reviews
Private room in bed and breakfast 3 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
breakfasts could be enjoyed inside looking out into a beautiful garden or outside on the deck
the space is very charming and comfortable
the space is cheery spacious private and comfortable
the place is clean and very comfortable
we found the spacious rooms both clean and warm
the house is wonderful clean comfortable
the rooms were all comfortable clean and well-stocked
mike and jody’s house is super clean and quiet
mike was a perfect host
hosts are very friendly and provide excellent hospitality
wonderful hosts mike and jody
hosts were pleasant and we enjoyed our stay
nice upper level accommodations and wonderful hosts
great place super location and beautiful home
great location on a quiet street but close to plenty to see and do
finally the location is great as the home is situated very near ravina botanical garden and shopping
super comfortable private and ideally located - mike's place was perfect for a long weekend while we visited family
beautiful neighborhood and close to some great area attractions (the chicago botanic gardens is amazing)
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Experience a high-quality vacation at Highland Park

Posh. Elegant. Lovely. Comfortable. These words fit the description of this beautiful city. There are so many things to do and discover here regardless of your preferences as to how you would like to spend a vacation somewhere. Its rich history, music and arts influence, gastronomic pleasures, world-class beaches, and tranquil nature parks are some of the reasons why Highland Park should be on the top of your to-visit list. This suburban city surely is the perfect escape from the busyness of your daily life.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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