Vacation rentals in Highwood
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Highwood
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Highwood vacation rentals
Other great vacation rentals in Highwood
Guest favorite
Home in Lake Forest
5.0 out of 5 average rating, 6 reviewsParkside Cottage Near the Train
Feb 19 – 26
$135 per night
Guest favorite
Apartment in Libertyville
4.9 out of 5 average rating, 87 reviews131 East Park Ave. #308
Nov 1 – 8
$80 per night
Guest favorite
Apartment in Highland Park
5.0 out of 5 average rating, 12 reviewsFull Apartment green oasis in law suite
Sep 19 – 26
$158 per night
Guest favorite
Guesthouse in Lake Forest
4.88 out of 5 average rating, 81 reviewsAdorable Carriage House East Lake Forest
Dec 2 – 9
$229 per night
Guest favorite
Home in Northbrook
5.0 out of 5 average rating, 15 reviewsNorthbrook Retreat with Ample Outdoor Space
Sep 10 – 17
$283 per night
Guest favorite
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 23 – 30
$147 per night
Superhost
Home in Highland Park
4.88 out of 5 average rating, 8 reviewsThe Sunset Manor - Luxe Mansion for Serene retreat
Oct 27 – Nov 3
$762 per night
Guest favorite
Cottage in Libertyville
5.0 out of 5 average rating, 23 reviewsWoodland Guest House-Vintage Libertyville Chicago
Sep 29 – Oct 6
$70 per night
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- Chicago Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom