Holiday rentals in Highland Park

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Top-rated holiday rentals in Highland Park

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

Guest favourite
Home in Highland Park
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.
24 Feb – 3 MarIndividual Host,
€ 532 per night
4.91 out of 5 average rating, 109 reviews
Superhost
Flat in Park Ridge
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
9–16 JanIndividual Host,
€ 142 per night
4.79 out of 5 average rating, 302 reviews
Guest favourite
Home in Beach Park
B’s Farmhouse Cottage 2-bedroom duplex.
Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.
15–22 JanIndividual Host,
€ 140 per night
4.98 out of 5 average rating, 158 reviews

Popular amenities for Highland Park holiday 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 holiday rentals in Highland Park

Guest favourite
Loft in West Dundee
Hip Urban Loft - Small Town Charm -124 LOFTS #2
29 May – 5 JunProfessional Host,
€ 159 per night
4.97 out of 5 average rating, 437 reviews
Superhost
Flat in Evanston
Adorable 1BR apartment near Northwestern
17–24 JulIndividual Host,
€ 159 per night
4.83 out of 5 average rating, 213 reviews
Superhost
Flat in Highland Park
Stunning & Stylish Downtown Studio - Highland Park
1–8 Aug
€ 143 per night
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Highland Park
Charming Ranch-Style Cottage
28 Dec – 4 Jan
€ 163 per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Guest house in Lake Forest
The Green Door - safe and calm with walkability
2–9 DecIndividual Host,
€ 107 per night
4.95 out of 5 average rating, 94 reviews
Guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
1–8 Sep
€ 291 per night
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Highland Park
A Wonderful Getaway Home on the North Shore!
17–24 Jan
€ 235 per night
4.83 out of 5 average rating, 41 reviews
Superhost
Home in Highland Park
The Sunset Manor - Luxe Mansion for Serene retreat
11–18 Apr
€ 773 per night
4.8 out of 5 average rating, 5 reviews
Guest favourite
Home in Highland Park
Sanctuary on the Ravine
6–13 May
€ 685 per night
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Libertyville
131 East Park Ave. #308
16–23 Nov
€ 100 per night
4.91 out of 5 average rating, 81 reviews
Guest favourite
Home in Wilmette
Unique porcelain-enamel paneled "Lustron" home
9–16 Jul
€ 185 per night
4.98 out of 5 average rating, 89 reviews
Guest favourite
Guest house in Arlington Heights
Cozy Chicago Suburban Apartment
17–24 Nov
€ 113 per night
5.0 out of 5 average rating, 19 reviews

Quick stats about holiday 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

€ 28 before taxes and fees

Destinations to explore

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