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.

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.

4–11 Mar

£459 per night
Superhost

Flat 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

27 Sept – 4 Oct

£123 per night
Guest favourite

Loft in West Dundee

4.97 out of 5 average rating, 436 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

30 Dec – 6 Jan

£137 per night

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

Superhost

Flat in Highland Park

5.0 out of 5 average rating, 59 reviews

Chic Studio in Downtown Highland Park near Metra

18–25 Jul

£117 per night
Guest favourite

Cottage in Highland Park

4.95 out of 5 average rating, 43 reviews

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

9–16 May

£244 per night
Superhost

Home in Highland Park

4.83 out of 5 average rating, 6 reviews

The Sunset Manor - Luxe Mansion for Serene retreat

31 Jan – 7 Feb

£732 per night
Guest favourite

Guest house in Lake Forest

4.87 out of 5 average rating, 78 reviews

Adorable Carriage House East Lake Forest

29 Dec – 5 Jan

£295 per night
Guest favourite

Flat in Libertyville

4.91 out of 5 average rating, 82 reviews

131 East Park Ave. #308

7–14 Oct

£86 per night
Superhost

Home in Lake Forest

4.92 out of 5 average rating, 85 reviews

Beautifully decorated ranch near beach & shops

31 Aug – 7 Sept

£357 per night
Guest favourite

Home in Waukegan

4.87 out of 5 average rating, 30 reviews

* Cozy Wauk-Townhse near navy base

18–25 May

£111 per night
Guest favourite

Home in Deerfield

4.96 out of 5 average rating, 24 reviews

Lake Forest Country Estate

16–23 May

£236 per night
Guest favourite

Cottage in Libertyville

5.0 out of 5 average rating, 20 reviews

Woodland Guest House-Vintage Libertyville Chicago

8–15 Aug

£70 per night
Guest favourite

Guest house in Arlington Heights

4.9 out of 5 average rating, 20 reviews

Cozy Chicago Suburban Apartment

19–26 Mar

£96 per night
Guest favourite

Home in North Chicago

4.94 out of 5 average rating, 51 reviews

The Perfect home for the family!

12–19 Aug

£174 per night
Guest favourite

Flat in Waukegan

4.91 out of 5 average rating, 78 reviews

Cozy 2 Bedroom Apt, 13 Mins From Naval Academy

7–14 Jun

£109 per night

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