Holiday rentals in Highwood
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Top-rated holiday rentals in Highwood
Guests agree: these stays are highly rated for location, cleanliness and more.
Home in Highland Park
4.91 out of 5 average rating, 109 reviewsRejuvenate 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.
4–11 Mar
Flat in Park Ridge
4.79 out of 5 average rating, 309 reviewsModern 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
27 Sept – 4 Oct
Loft in West Dundee
4.97 out of 5 average rating, 436 reviewsHip 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
30 Dec – 6 Jan
Holiday rentals for every style
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Popular amenities for Highwood holiday rentals
Other great holiday rentals in Highwood
Flat in Highland Park
5.0 out of 5 average rating, 59 reviewsChic Studio in Downtown Highland Park near Metra
18–25 Jul
Cottage in Highland Park
4.95 out of 5 average rating, 43 reviewsRe-imagined 1880s cottage by Highwood, Metra, Lake
9–16 May
Home in Highland Park
4.83 out of 5 average rating, 6 reviewsThe Sunset Manor - Luxe Mansion for Serene retreat
31 Jan – 7 Feb
Guest house in Lake Forest
4.87 out of 5 average rating, 78 reviewsAdorable Carriage House East Lake Forest
29 Dec – 5 Jan
Flat in Libertyville
4.91 out of 5 average rating, 82 reviews131 East Park Ave. #308
7–14 Oct
Home in Lake Forest
4.92 out of 5 average rating, 85 reviewsBeautifully decorated ranch near beach & shops
31 Aug – 7 Sept
Home in Waukegan
4.87 out of 5 average rating, 30 reviews* Cozy Wauk-Townhse near navy base
18–25 May
Home in Deerfield
4.96 out of 5 average rating, 24 reviewsLake Forest Country Estate
16–23 May
Cottage in Libertyville
5.0 out of 5 average rating, 20 reviewsWoodland Guest House-Vintage Libertyville Chicago
8–15 Aug
Guest house in Arlington Heights
4.9 out of 5 average rating, 20 reviewsCozy Chicago Suburban Apartment
19–26 Mar
Home in North Chicago
4.94 out of 5 average rating, 51 reviewsThe Perfect home for the family!
12–19 Aug
Flat in Waukegan
4.91 out of 5 average rating, 78 reviewsCozy 2 Bedroom Apt, 13 Mins From Naval Academy
7–14 Jun
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