Vacation rentals in Highland Park

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Top-rated vacation rentals in Highland Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Home in Highland Park

4.91 out of 5 average rating, 109 reviews

Rejuvenate and Relax in the North Shore

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

Apr 24 – May 1

$422 per night
Guest favorite

Loft in West Dundee

4.97 out of 5 average rating, 437 reviews

Hip Urban Loft - Small Town Charm -124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

Oct 13 – 20

$128 per night
Superhost

Apartment in Park Ridge

4.79 out of 5 average rating, 309 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Jul 1 – 8

$128 per night

Popular amenities for Highland Park vacation rentals

Stay near Highland Park's top sights

Whole Foods Market5 locals recommend
Lake-Cook /Chicago Botanic Garden station14 locals recommend
Ravinia Festival West Lot33 locals recommend
Rosewood Beach7 locals recommend
Jewel-Osco9 locals recommend
Miramar Bistro7 locals recommend

Other great vacation rentals in Highland Park

Guest favorite

Apartment in Winthrop Harbor

4.95 out of 5 average rating, 221 reviews

Love my guests! Homey Elegant & Lake Michigan!

Jul 28 – Aug 4

$68 per night
Guest favorite

Apartment in Evanston

4.96 out of 5 average rating, 399 reviews

Charming, Sunny Apartment with Backyard Garden

Mar 13 – 20

$124 per night
Superhost

Apartment in Highland Park

5.0 out of 5 average rating, 59 reviews

Chic Studio in Downtown Highland Park near Metra

Jul 6 – 13

$115 per night
Guest favorite

Home in Highland Park

4.98 out of 5 average rating, 49 reviews

Charming Ranch-Style Cottage

Oct 25 – Nov 1

$143 per night
Guest favorite

Guesthouse in Lake Forest

4.95 out of 5 average rating, 93 reviews

The Green Door - safe and calm with walkability

Jan 29 – Feb 5

$85 per night
Guest favorite

Cottage in Highland Park

4.95 out of 5 average rating, 43 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Sep 9 – 16

$245 per night
Guest favorite

Home in Highland Park

5.0 out of 5 average rating, 22 reviews

Sanctuary on the Ravine

Oct 14 – 21

$399 per night
Guest favorite

Home in Highland Park

4.85 out of 5 average rating, 41 reviews

A Wonderful Getaway Home on the North Shore!

Sep 23 – 30

$188 per night
Superhost

Home in Highland Park

4.81 out of 5 average rating, 26 reviews

Modern Luxe Home w/Gameroom and Electric Fireplace

Feb 7 – 14

$469 per night
Guest favorite

Apartment in Libertyville

4.91 out of 5 average rating, 82 reviews

131 East Park Ave. #308

Sep 12 – 19

$77 per night
Superhost

Home in Lake Forest

4.92 out of 5 average rating, 85 reviews

Beautifully decorated ranch near beach & shops

Dec 10 – 17

$357 per night
Guest favorite

Guesthouse in Lake Forest

4.87 out of 5 average rating, 79 reviews

Adorable Carriage House East Lake Forest

Sep 21 – 28

$257 per night

Quick stats about vacation rentals in Highland Park

Total rentals

50 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.6K reviews

Nightly prices starting at

$30 before taxes and fees

Frequently Asked Questions

  • Do house rentals in Highland Park have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Highland Park. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Highland Park?

    Yes! Work meets play with ease at over 30 vacation rentals in Highland Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Highland Park have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Highland Park. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Highland Park?

    Experience the best of Highland Park with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Highland Park?

    Four-legged friends are welcome in Highland Park. Choose from more than 20 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for Apartment Rentals in Highland Park?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Highland Park?

    Highland Park has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Highland Park have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Highland Park. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Lake County
  5. Highland Park