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. For more fun, you might want to see the attractions in Chicago — this city is just a short drive away.
To have a full experience of the city’s posh lifestyle, check out the following Airbnb vacation rentals in Highland Park, Illinois.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on May 20, 2024.
1. Classy private home with a pool (from USD 1000)
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.
Highland Park, Illinois, United States
3.51 km (2.2 mi) from Fort Sheridan Forest PreserveSuperhostAccommodates: 15
Top guest reviews
Amenities & Room:
with 6 bedrooms and 4 bathrooms it easily accommodated our familyfirst the good stuff:the beds were really comfortable and the furniture inside was really nice and well decoratedgorgeous stylish home plenty of room for our group of 8we were immediately impressed with the size and beautiful decor and gourmet well stocked kitchenhighly recommended clean great bbq grill great pool lots of house space beautiful propertyCleanliness:
this was an amazing clean relaxing place to staybeautiful spacious and spotlessly clean home in an excellent locationhome is very clean and spaciousthe place was very clean and had all of the necessities for a few nights staythe house was wonderful just as described it was very neat and clean and had welcoming touchesHost:
kailash was an outstanding hostamazing stay very thoughtful hostthe host was amazing checked on us during our stay to make sure we didn’t need anythingkailash is a wonderful host this was by far my best airbnb experiencethis place was beyond gorgeous and kailash was very helpful and responsive he even stopped by to assist usRead more reviewsLocation:
beautiful area/ trails for walking and running nice trails close to housegreat place and perfect location and distance from navy yard and airportthe neighborhood is quiet and is in a perfect locationgreat house for families great locationfantastic location close to restaurants shopping great lakes navy base and so much more
2. Exquisite four-bedroom retreat (from USD 477)
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.
Highland Park, Illinois, United States
2.85 km (1.8 mi) from Fort Sheridan Forest PreserveSuperhostAccommodates: 12
Top guest reviews
Amenities & Room:
the kids liked the air hockey and tv in the downstairs areaall beds were comfortable and we lacked for nothing as far as supplies and amenitiesthe beds are very comfortable and the linen closet is well stockedthe beds are comfortable and the linens are high qualitymy family loved all the rooms with beautiful beddingCleanliness:
it is extremely clean and thoughtfully decoratedthe house is spacious well stocked and cleanthe place was clean spacious and in a good locationcomfy clean well located good communicationthe hallway closet upstairs was packed full of clean towelsHost:
the hosts were very helpfullana and luca are great hostscommunicative and courteous hostthey were quick and responsive when we had questionslana and luca were great hosts very responsive to all our questions before and during our stayRead more reviewsLocation:
it is an easy walk to very good restaurantsthis is a wonderful property in a great locationthe location was perfect for our needs and the house was toothe house is in a very nice area and centrally located within highland parkwe found this house to be a nice place to stay in highland park
3. Room in a homey oasis nestled on a quiet residential street (from USD 48)
This cheap apartment in Highland Park 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, Illinois, United States
2.8 km (1.8 mi) from Fort Sheridan Forest PreserveAccommodates: 3
Top guest reviews
Amenities & Room:
i also enjoyed the amish rocking chair in my room next to a little reading lampit's quiet in the evenings and the bed was very comfortable - perfect for a good nights' restmy stay with her was incredibly comfortable and restfulthe two beds make it a perfect spot for a friends tripCleanliness:
the room was clean cozy and quietroom was clean with plenty of spacethere is a shared bathroom - comfortable and cleanthe bedroom was quaint clean and comfortablethe room was so clean and smelled fresh and the bed was comfyHost:
the host was amazingthank you for being a great hostmarjorie is a great hostmarjorie was very responsivemarjorie is a very gracious hostRead more reviewsLocation:
great location and affordable pricegood location for workwonderful location for those getting away from the hustle and bustlethis is a great location in highland parkgreat location good value for money
4. Elegant yet comfortable historic chateau
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.
Highland Park, Illinois, United States
5.62 km (3.5 mi) from Fort Sheridan Forest PreserveAccommodates: 6
Top guest reviews
Host:
hosts were greatthe home is lovely a restored treasure in highland park accommodations wonderful hosts superb and attentivejeff and john are fantastic hosts we will returnjeff was a wonderful host and the home was beautiful and sparkling cleanthanks to jeff for being a wonderful and responsive hostRead more reviewsLocation:
ideal location and only a 40minute train to downtownthe location is beautiful and close to downtown highland park for restaurants and shoppingclose proximity to ravina festival grounds the lake and a water parkgreat upscale neighborhood walking distance to grocery quaint downtownwe felt safe and comfortable our whole stay and it was in a great location
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.
This apartment for rent in Highland Park features rooms that 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.
Highland Park, Illinois, United States
7.79 km (4.9 mi) from Fort Sheridan Forest PreserveTop guest reviews
Amenities & Room:
breakfasts could be enjoyed inside looking out into a beautiful garden or outside on the deckthe space is very charming and comfortablethe space is cheery spacious private and comfortableCleanliness:
the place is clean and very comfortablewe found the spacious rooms both clean and warmthe house is wonderful clean comfortablethe rooms were all comfortable clean and well-stockedmike and jody’s house is super clean and quietHost:
mike was a perfect hosthosts are very friendly and provide excellent hospitalitywonderful hosts mike and jodyhosts were pleasant and we enjoyed our staynice upper level accommodations and wonderful hostsRead more reviewsLocation:
great place super location and beautiful homegreat location on a quiet street but close to plenty to see and dofinally the location is great as the home is situated very near ravina botanical garden and shoppingsuper comfortable private and ideally located - mike's place was perfect for a long weekend while we visited familybeautiful neighborhood and close to some great area attractions (the chicago botanic gardens is amazing)
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. If you want to spend 36 hours in Chicago, just exploring everything this historic city has to offer, you can easily do so since it’s near Highland Park.
There are just many things to do when you stay here. So, to have the most of your time, book one of the homes for rent in Highland Park mentioned above.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to