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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
49 rentals in Highland Park.
Modern Luxe home w/Gameroom and Electric Fireplace, holiday rental in Highland Park
Modern Luxe home w/Gameroom and Electric Fireplace, holiday rental in Highland Park
Modern Luxe home w/Gameroom and Electric Fireplace, holiday rental in Highland Park

Modern Luxe home w/Gameroom and Electric Fireplace

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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
More info
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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
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Picturesque! Mid Mod Home - 20min from Chicago!, holiday rental in Highland Park
Picturesque! Mid Mod Home - 20min from Chicago!, holiday rental in Highland Park
Picturesque! Mid Mod Home - 20min from Chicago!, holiday rental in Highland Park

Picturesque! Mid Mod Home - 20min from Chicago!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
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 following properties within 32 kms of Highland Park match all your filters:
Chicago - Wilmette  Luxury 3 Story Victorian Mansion High End  7 min to Beach, holiday rental in Highland Park
Chicago - Wilmette  Luxury 3 Story Victorian Mansion High End  7 min to Beach, holiday rental in Highland Park
Chicago - Wilmette  Luxury 3 Story Victorian Mansion High End  7 min to Beach, holiday rental in Highland Park

Chicago - Wilmette Luxury 3 Story Victorian Mansion High End 7 min to Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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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
0 bedrooms
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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lovely 1 bedroom Near Great Lakes Naval, holiday rental in Highland Park
Lovely 1 bedroom Near Great Lakes Naval, holiday rental in Highland Park
Lovely 1 bedroom Near Great Lakes Naval, holiday rental in Highland Park

Lovely 1 bedroom Near Great Lakes Naval

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
More info
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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
More info
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Quite Peaceful Glenview escapes., holiday rental in Highland Park
Quite Peaceful Glenview escapes., holiday rental in Highland Park
Quite Peaceful Glenview escapes., holiday rental in Highland Park

Quite Peaceful Glenview escapes.

Holiday Rental House
2 bedrooms
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
More info
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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
More info
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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
More info
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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 2
Match: Sleeps
More info
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Quite peaceful escape in Northbrook, holiday rental in Highland Park
Quite peaceful escape in Northbrook, holiday rental in Highland Park
Quite peaceful escape in Northbrook, holiday rental in Highland Park

Quite peaceful escape in Northbrook

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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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
More info
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2 Bedroom apartment in Downtown Lake Bluff, holiday rental in Highland Park
2 Bedroom apartment in Downtown Lake Bluff, holiday rental in Highland Park
2 Bedroom apartment in Downtown Lake Bluff, holiday rental in Highland Park

2 Bedroom apartment in Downtown Lake Bluff

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
More info
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Two Bed/1 Bath Apartment -  East Lake Bluff, Illinois, holiday rental in Highland Park
Two Bed/1 Bath Apartment -  East Lake Bluff, Illinois, holiday rental in Highland Park
Two Bed/1 Bath Apartment -  East Lake Bluff, Illinois, holiday rental in Highland Park

Two Bed/1 Bath Apartment - East Lake Bluff, Illinois

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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3 Bedroom 1 Bath Near Great Lakes Naval, holiday rental in Highland Park
3 Bedroom 1 Bath Near Great Lakes Naval, holiday rental in Highland Park
3 Bedroom 1 Bath Near Great Lakes Naval, holiday rental in Highland Park

3 Bedroom 1 Bath Near Great Lakes Naval

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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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
More info
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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
More info
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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
More info
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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
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wheeling FHS Rental, holiday rental in Highland Park
Wheeling FHS Rental, holiday rental in Highland Park
Wheeling FHS Rental, holiday rental in Highland Park

Wheeling FHS Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
More info
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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
More info
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Extended Stay Northbrook FHS Rental, holiday rental in Highland Park
Extended Stay Northbrook FHS Rental, holiday rental in Highland Park
Extended Stay Northbrook FHS Rental, holiday rental in Highland Park

Extended Stay Northbrook FHS Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Northbrook FHS Rental, holiday rental in Highland Park
Northbrook FHS Rental, holiday rental in Highland Park
Northbrook FHS Rental, holiday rental in Highland Park

Northbrook FHS Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
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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
More info
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Luxury House w/ all amenities at Lake Forest, holiday rental in Highland Park
Luxury House w/ all amenities at Lake Forest, holiday rental in Highland Park
Luxury House w/ all amenities at Lake Forest, holiday rental in Highland Park

Luxury House w/ all amenities at Lake Forest

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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North Shore 4 bedroom home near New Trier Schools, holiday rental in Highland Park
North Shore 4 bedroom home near New Trier Schools, holiday rental in Highland Park
North Shore 4 bedroom home near New Trier Schools, holiday rental in Highland Park

North Shore 4 bedroom home near New Trier Schools

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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Dreams Turum Riviera maya , holiday rental in Highland Park
Dreams Turum Riviera maya , holiday rental in Highland Park
Dreams Turum Riviera maya , holiday rental in Highland Park

Dreams Turum Riviera maya

Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Ultimate Romantic Experience & Getaway for Two!, holiday rental in Highland Park
The Ultimate Romantic Experience & Getaway for Two!, holiday rental in Highland Park
The Ultimate Romantic Experience & Getaway for Two!, holiday rental in Highland Park

The Ultimate Romantic Experience & Getaway for Two!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-49 of 49
Frequently Asked Questions about Highland Park