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Holiday Rentals in Highland Park

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
48 rentals in Highland Park.
Chic Studio - In Downtown Highland Park, by Metra, holiday rental in Highland Park
Chic Studio - In Downtown Highland Park, by Metra, holiday rental in Highland Park
Chic Studio - In Downtown Highland Park, by Metra, holiday rental in Highland Park

Chic Studio - In Downtown Highland Park, by Metra

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia, holiday rental in Highland Park
Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia, holiday rental in Highland Park
Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia, holiday rental in Highland Park

Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Safe and Secure, Charming, Clean Studio, holiday rental in Highland Park
Safe and Secure, Charming, Clean Studio, holiday rental in Highland Park
Safe and Secure, Charming, Clean Studio, holiday rental in Highland Park

Safe and Secure, Charming, Clean Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan, holiday rental in Highland Park
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan, holiday rental in Highland Park
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan, holiday rental in Highland Park

Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Serene Retreat Awaits You!, holiday rental in Highland Park
Serene Retreat Awaits You!, holiday rental in Highland Park
Serene Retreat Awaits You!, holiday rental in Highland Park

Serene Retreat Awaits You!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The Sunset Manor - Luxe Mansion for Serene retreat, holiday rental in Highland Park
The Sunset Manor - Luxe Mansion for Serene retreat, holiday rental in Highland Park
The Sunset Manor - Luxe Mansion for Serene retreat, holiday rental in Highland Park

The Sunset Manor - Luxe Mansion for Serene retreat

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Stunning & Stylish Downtown Studio - Highland Park, holiday rental in Highland Park
Stunning & Stylish Downtown Studio - Highland Park, holiday rental in Highland Park
Stunning & Stylish Downtown Studio - Highland Park, holiday rental in Highland Park

Stunning & Stylish Downtown Studio - Highland Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Chic Studio in Downtown Highland Park near Metra, holiday rental in Highland Park
Chic Studio in Downtown Highland Park near Metra, holiday rental in Highland Park
Chic Studio in Downtown Highland Park near Metra, holiday rental in Highland Park

Chic Studio in Downtown Highland Park near Metra

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town, holiday rental in Highland Park
Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town, holiday rental in Highland Park
Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town, holiday rental in Highland Park

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Safe & Secure Parkview-Sleep Sanctuary+Kitchen, holiday rental in Highland Park
Safe & Secure Parkview-Sleep Sanctuary+Kitchen, holiday rental in Highland Park
Safe & Secure Parkview-Sleep Sanctuary+Kitchen, holiday rental in Highland Park

Safe & Secure Parkview-Sleep Sanctuary+Kitchen

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The following properties within 32 kms of Highland Park match all your filters:
Charming home near Lake Michigan, bike paths, and high school, holiday rental in Highland Park
Charming home near Lake Michigan, bike paths, and high school, holiday rental in Highland Park
Charming home near Lake Michigan, bike paths, and high school, holiday rental in Highland Park

Charming home near Lake Michigan, bike paths, and high school

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown, holiday rental in Highland Park
Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown, holiday rental in Highland Park
Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown, holiday rental in Highland Park

Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast, holiday rental in Highland Park
Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast, holiday rental in Highland Park
Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast, holiday rental in Highland Park

Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pool Access + Daily Free Breakfast Included!, holiday rental in Highland Park
Pool Access + Daily Free Breakfast Included!, holiday rental in Highland Park
Pool Access + Daily Free Breakfast Included!, holiday rental in Highland Park

Pool Access + Daily Free Breakfast Included!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful self contained apartment downtown Lake Bluff, holiday rental in Highland Park
Beautiful self contained apartment downtown Lake Bluff, holiday rental in Highland Park
Beautiful self contained apartment downtown Lake Bluff, holiday rental in Highland Park

Beautiful self contained apartment downtown Lake Bluff

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business, holiday rental in Highland Park
Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business, holiday rental in Highland Park
Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business, holiday rental in Highland Park

Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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In "The Glen" Business District. Free Breakfast. Indoor Pool. Studio at, holiday rental in Highland Park
In "The Glen" Business District. Free Breakfast. Indoor Pool. Studio at, holiday rental in Highland Park
In "The Glen" Business District. Free Breakfast. Indoor Pool. Studio at, holiday rental in Highland Park

In "The Glen" Business District. Free Breakfast. Indoor Pool. Studio at

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Studio | Free Breakfast! Heated Indoor Pool, holiday rental in Highland Park
Studio | Free Breakfast! Heated Indoor Pool, holiday rental in Highland Park
Studio | Free Breakfast! Heated Indoor Pool, holiday rental in Highland Park

Studio | Free Breakfast! Heated Indoor Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Business District Suite with Pool Access, Free Breakfast + Weekday Shuttle, holiday rental in Highland Park
Business District Suite with Pool Access, Free Breakfast + Weekday Shuttle, holiday rental in Highland Park
Business District Suite with Pool Access, Free Breakfast + Weekday Shuttle, holiday rental in Highland Park

Business District Suite with Pool Access, Free Breakfast + Weekday Shuttle

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast, holiday rental in Highland Park
Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast, holiday rental in Highland Park
Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast, holiday rental in Highland Park

Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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1 Bedroom | Free Breakfast, Indoor Pool Access, holiday rental in Highland Park
1 Bedroom | Free Breakfast, Indoor Pool Access, holiday rental in Highland Park
1 Bedroom | Free Breakfast, Indoor Pool Access, holiday rental in Highland Park

1 Bedroom | Free Breakfast, Indoor Pool Access

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Guests Get Free Breakfast Daily! In "The Glen" District. Indoor Pool, holiday rental in Highland Park
Guests Get Free Breakfast Daily! In "The Glen" District. Indoor Pool, holiday rental in Highland Park
Guests Get Free Breakfast Daily! In "The Glen" District. Indoor Pool, holiday rental in Highland Park

Guests Get Free Breakfast Daily! In "The Glen" District. Indoor Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stay in "The Glen" Business District! Free Breakfast, Pool. | Staybridge, holiday rental in Highland Park
Stay in "The Glen" Business District! Free Breakfast, Pool. | Staybridge, holiday rental in Highland Park
Stay in "The Glen" Business District! Free Breakfast, Pool. | Staybridge, holiday rental in Highland Park

Stay in "The Glen" Business District! Free Breakfast, Pool. | Staybridge

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Equipped Corporate Center Suite with Pool Access + Free Breakfast, holiday rental in Highland Park
Equipped Corporate Center Suite with Pool Access + Free Breakfast, holiday rental in Highland Park
Equipped Corporate Center Suite with Pool Access + Free Breakfast, holiday rental in Highland Park

Equipped Corporate Center Suite with Pool Access + Free Breakfast

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Master qtr close to nature & easy urban facilities, holiday rental in Highland Park
Master qtr close to nature & easy urban facilities, holiday rental in Highland Park
Master qtr close to nature & easy urban facilities, holiday rental in Highland Park

Master qtr close to nature & easy urban facilities

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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King Suite in "The Glen" District. Free Breakfast Daily. Indoor Pool, holiday rental in Highland Park
King Suite in "The Glen" District. Free Breakfast Daily. Indoor Pool, holiday rental in Highland Park
King Suite in "The Glen" District. Free Breakfast Daily. Indoor Pool, holiday rental in Highland Park

King Suite in "The Glen" District. Free Breakfast Daily. Indoor Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Family union get together, holiday rental in Highland Park
Family union get together, holiday rental in Highland Park
Family union get together, holiday rental in Highland Park

Family union get together

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast, holiday rental in Highland Park
Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast, holiday rental in Highland Park
Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast, holiday rental in Highland Park

Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Rivendell is a historic duplex home., holiday rental in Highland Park
Rivendell is a historic duplex home., holiday rental in Highland Park
Rivendell is a historic duplex home., holiday rental in Highland Park

Rivendell is a historic duplex home.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Mid-century design home located in the Villas of Lake Bluff, holiday rental in Highland Park
Mid-century design home located in the Villas of Lake Bluff, holiday rental in Highland Park
Mid-century design home located in the Villas of Lake Bluff, holiday rental in Highland Park

Mid-century design home located in the Villas of Lake Bluff

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden, holiday rental in Highland Park
Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden, holiday rental in Highland Park
Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden, holiday rental in Highland Park

Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Contemporary Suite in "The Glen" Business District | 24 Hour Fitness Center, holiday rental in Highland Park
Contemporary Suite in "The Glen" Business District | 24 Hour Fitness Center, holiday rental in Highland Park
Contemporary Suite in "The Glen" Business District | 24 Hour Fitness Center, holiday rental in Highland Park

Contemporary Suite in "The Glen" Business District | 24 Hour Fitness Center

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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"The Glen" District Suite with A/C | Business Center + Heated Indoor Pool!, holiday rental in Highland Park
"The Glen" District Suite with A/C | Business Center + Heated Indoor Pool!, holiday rental in Highland Park
"The Glen" District Suite with A/C | Business Center + Heated Indoor Pool!, holiday rental in Highland Park

"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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Entire Beautiful Wheeling Home!!!, holiday rental in Highland Park
Entire Beautiful Wheeling Home!!!, holiday rental in Highland Park
Entire Beautiful Wheeling Home!!!, holiday rental in Highland Park

Entire Beautiful Wheeling Home!!!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Warm and Cheerful 3 Bedroom Winnetka Townhouse, holiday rental in Highland Park
Warm and Cheerful 3 Bedroom Winnetka Townhouse, holiday rental in Highland Park
Warm and Cheerful 3 Bedroom Winnetka Townhouse, holiday rental in Highland Park

Warm and Cheerful 3 Bedroom Winnetka Townhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cute Ranch House close to town monthly stay, holiday rental in Highland Park
Cute Ranch House close to town monthly stay, holiday rental in Highland Park
Cute Ranch House close to town monthly stay, holiday rental in Highland Park

Cute Ranch House close to town monthly stay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Northbrook Rental, holiday rental in Highland Park
Northbrook Rental, holiday rental in Highland Park
Northbrook Rental, holiday rental in Highland Park

Northbrook Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!, holiday rental in Highland Park
Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!, holiday rental in Highland Park
Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!, holiday rental in Highland Park

Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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6 Bedrooms Home Suburbs of Chicago, holiday rental in Highland Park
6 Bedrooms Home Suburbs of Chicago, holiday rental in Highland Park
6 Bedrooms Home Suburbs of Chicago, holiday rental in Highland Park

6 Bedrooms Home Suburbs of Chicago

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Charming 4-bedroom ranch house near downtown Lake Forest with AC, WiFi, holiday rental in Highland Park
Charming 4-bedroom ranch house near downtown Lake Forest with AC, WiFi, holiday rental in Highland Park
Charming 4-bedroom ranch house near downtown Lake Forest with AC, WiFi, holiday rental in Highland Park

Charming 4-bedroom ranch house near downtown Lake Forest with AC, WiFi

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Northbrook Rental, holiday rental in Highland Park
Northbrook Rental, holiday rental in Highland Park
Northbrook Rental, holiday rental in Highland Park

Northbrook Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Contemporary house with partial lake views/quiet and private area/gut, holiday rental in Highland Park
Contemporary house with partial lake views/quiet and private area/gut, holiday rental in Highland Park
Contemporary house with partial lake views/quiet and private area/gut, holiday rental in Highland Park

Contemporary house with partial lake views/quiet and private area/gut

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 5BR/6BA Gorgeous Home in Fabulous Northshore Chicago location!, holiday rental in Highland Park
Spacious 5BR/6BA Gorgeous Home in Fabulous Northshore Chicago location!, holiday rental in Highland Park
Spacious 5BR/6BA Gorgeous Home in Fabulous Northshore Chicago location!, holiday rental in Highland Park

Spacious 5BR/6BA Gorgeous Home in Fabulous Northshore Chicago location!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Coveted Location:Downtown Lake Forest 3/2.5 Duplex, holiday rental in Highland Park
Coveted Location:Downtown Lake Forest 3/2.5 Duplex, holiday rental in Highland Park
Coveted Location:Downtown Lake Forest 3/2.5 Duplex, holiday rental in Highland Park

Coveted Location:Downtown Lake Forest 3/2.5 Duplex

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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1 Bedroom | Free Breakfast Buffet, Indoor Pool, holiday rental in Highland Park
1 Bedroom | Free Breakfast Buffet, Indoor Pool, holiday rental in Highland Park
1 Bedroom | Free Breakfast Buffet, Indoor Pool, holiday rental in Highland Park

1 Bedroom | Free Breakfast Buffet, Indoor Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Mid-Term Rental Entire Home In Glenview, holiday rental in Highland Park
Amazing Mid-Term Rental Entire Home In Glenview, holiday rental in Highland Park
Amazing Mid-Term Rental Entire Home In Glenview, holiday rental in Highland Park

Amazing Mid-Term Rental Entire Home In Glenview

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming 2-bedroom home in fantastic Winnetka, IL location, holiday rental in Highland Park
Charming 2-bedroom home in fantastic Winnetka, IL location, holiday rental in Highland Park
Charming 2-bedroom home in fantastic Winnetka, IL location, holiday rental in Highland Park

Charming 2-bedroom home in fantastic Winnetka, IL location

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Entire home, close to highway, serene neighborhood, holiday rental in Highland Park
Entire home, close to highway, serene neighborhood, holiday rental in Highland Park
Entire home, close to highway, serene neighborhood, holiday rental in Highland Park

Entire home, close to highway, serene neighborhood

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Highland Park