Holiday rentals in Highwood

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highwood

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,
£455 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,
£122 per night
4.79 out of 5 average rating, 302 reviews
Guest favourite
Loft in West Dundee
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
29 May – 5 JunProfessional Host,
£136 per night
4.97 out of 5 average rating, 437 reviews

Popular amenities for Highwood holiday rentals

Stay near Highwood's top sights

Miramar Bistro7 locals recommend
Buffo's5 locals recommend
Tala Coffee Roasters - Highwood Cafe3 locals recommend
Disotto3 locals recommend
La Plancha Loca3 locals recommend
Del Rio Restaurant4 locals recommend

Other great holiday rentals in Highwood

Guest favourite
Guest house in Lake Forest
The Green Door - safe and calm with walkability
15–22 AprIndividual Host,
£92 per night
4.95 out of 5 average rating, 94 reviews
Superhost
Flat in Highland Park
Stunning & Stylish Downtown Studio - Highland Park
1–8 Aug
£122 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
£140 per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
1–8 Sept
£248 per night
4.95 out of 5 average rating, 42 reviews
Superhost
Home in Highland Park
The Sunset Manor - Luxe Mansion for Serene retreat
20–27 Oct
£777 per night
4.8 out of 5 average rating, 5 reviews
Guest favourite
Guest house in Lake Forest
Adorable Carriage House East Lake Forest
15–22 Aug
£332 per night
4.87 out of 5 average rating, 78 reviews
Guest favourite
Flat in Libertyville
131 East Park Ave. #308
16–23 Nov
£86 per night
4.91 out of 5 average rating, 81 reviews
Superhost
Home in Lake Forest
Beautifully decorated ranch near beach & shops
18–25 Dec
£348 per night
4.92 out of 5 average rating, 84 reviews
Guest favourite
Home in Waukegan
* Cozy Wauk-Townhse near navy base
2–9 Dec
£110 per night
4.86 out of 5 average rating, 29 reviews
Guest favourite
Guest house in Arlington Heights
Cozy Chicago Suburban Apartment
17–24 Nov
£96 per night
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Wilmette
Unique porcelain-enamel paneled "Lustron" home
9–16 Jul
£159 per night
4.98 out of 5 average rating, 89 reviews
Guest favourite
Home in Highland Park
A Wonderful Getaway Home on the North Shore!
11–18 Nov
£202 per night
4.83 out of 5 average rating, 41 reviews

Destinations to explore

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