Highland Park Vacation Rentals
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Bedrooms
Bathrooms
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Property type
Distinctive Features
Distance from
5 mi
50 rentals in Highland Park.
Serene Retreat Awaits You!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Picturesque! Mid Mod Home - 20min from Chicago!
Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Chic Studio - In Downtown Highland Park, by Metra
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Modern Luxe home w/Gameroom and Electric Fireplace
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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Safe and Secure, Charming, Clean Studio
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
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Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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The following properties within 20 miles of Highland Park match all your filters:
Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Master qtr close to nature & easy urban facilities
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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"The Glen" District Suite with A/C | Business Center + Heated Indoor Pool!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Warm and Cheerful 3 Bedroom Winnetka Townhouse
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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6 Bedrooms Home Suburbs of Chicago
Rental Home
6 bedrooms
6 bathrooms
Sleeps 20
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Equipped Corporate Center Suite with Pool Access + Free Breakfast
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Rivendell is a historic duplex home.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Contemporary Suite in "The Glen" Business District | 24 Hour Fitness Center
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Two Bed/1 Bath Apartment - East Lake Bluff, Illinois
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
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Luxury House w/ all amenities at Lake Forest
Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Chicago - Wilmette Luxury 3 Story Victorian Mansion High End 7 min to Beach
Rental Home
4 bedrooms
5 bathrooms
Sleeps 7
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Business District Suite with Pool Access, Free Breakfast + Weekday Shuttle
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Guests Get Free Breakfast Daily! In "The Glen" District. Indoor Pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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King Suite in "The Glen" District. Free Breakfast Daily. Indoor Pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Stay in "The Glen" Business District! Free Breakfast, Pool. | Staybridge
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Dreams Turum Riviera maya
Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 10
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Cute Ranch House close to town monthly stay
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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North Shore 4 bedroom home near New Trier Schools
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Charming home near Lake Michigan, bike paths, and high school
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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1 Bedroom | Free Breakfast, Indoor Pool Access
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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2 Bedroom apartment in Downtown Lake Bluff
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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1 Bedroom | Free Breakfast Buffet, Indoor Pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
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Beautiful self contained apartment downtown Lake Bluff
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Elegant Riverwoods Escape w/ Private Sauna!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
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Mid-century design home located in the Villas of Lake Bluff
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Northbrook FHS Rental
Rental Home
3 bedrooms
2 bathrooms
Sleeps 13
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Extended Stay Northbrook FHS Rental
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Northbrook Rental
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Charming Convenient Wilmette Home
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Northbrook Rental
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Entire Beautiful Wheeling Home!!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Studio | Free Breakfast! Heated Indoor Pool
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Lovely 1 bedroom Near Great Lakes Naval
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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3 Bedroom 1 Bath Near Great Lakes Naval
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
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2 Bedroom Near Great Lakes Naval
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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In "The Glen" Business District. Free Breakfast. Indoor Pool. Studio at
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Pool Access + Daily Free Breakfast Included!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Showing results 1-50 of 50
Frequently Asked Questions about Highland Park
- Yes, here are some popular vacation rentals in Highland Park that have a pool:
- Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
- Serene Retreat Awaits You!
- Chic Studio - In Downtown Highland Park, by Metra
- Yes, here are some popular vacation rentals in Highland Park that have internet access:
- Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
- Serene Retreat Awaits You!
- Chic Studio - In Downtown Highland Park, by Metra
- Some of the most popular kid friendly rentals in Highland Park are:
- Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
- Serene Retreat Awaits You!
- Chic Studio - In Downtown Highland Park, by Metra