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Holiday Rentals in Winnetka

Destination
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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
50 rentals in Winnetka.
Warm and Cheerful 3 Bedroom Winnetka Townhouse, holiday rental in Winnetka
Warm and Cheerful 3 Bedroom Winnetka Townhouse, holiday rental in Winnetka
Warm and Cheerful 3 Bedroom Winnetka Townhouse, holiday rental in Winnetka

Warm and Cheerful 3 Bedroom Winnetka Townhouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The following properties within 32 kms of Winnetka match all your filters:
Special Skevanston Space 2mi to Northwestern University & beach, holiday rental in Winnetka
Special Skevanston Space 2mi to Northwestern University & beach, holiday rental in Winnetka
Special Skevanston Space 2mi to Northwestern University & beach, holiday rental in Winnetka

Special Skevanston Space 2mi to Northwestern University & beach

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chicago Family Apartment - Kids & Pets Welcome!, holiday rental in Winnetka
Chicago Family Apartment - Kids & Pets Welcome!, holiday rental in Winnetka
Chicago Family Apartment - Kids & Pets Welcome!, holiday rental in Winnetka

Chicago Family Apartment - Kids & Pets Welcome!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Chicago - Wilmette  Luxury 3 Story Victorian Mansion High End  7 min to Beach, holiday rental in Winnetka
Chicago - Wilmette  Luxury 3 Story Victorian Mansion High End  7 min to Beach, holiday rental in Winnetka
Chicago - Wilmette  Luxury 3 Story Victorian Mansion High End  7 min to Beach, holiday rental in Winnetka

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
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Free Parking, Private Terrace Sunny 2bd/1bth, holiday rental in Winnetka
Free Parking, Private Terrace Sunny 2bd/1bth, holiday rental in Winnetka
Free Parking, Private Terrace Sunny 2bd/1bth, holiday rental in Winnetka

Free Parking, Private Terrace Sunny 2bd/1bth

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy Old Chicago - 4 Bedroom, holiday rental in Winnetka
Cozy Old Chicago - 4 Bedroom, holiday rental in Winnetka
Cozy Old Chicago - 4 Bedroom, holiday rental in Winnetka

Cozy Old Chicago - 4 Bedroom

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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DVN Fascinating 1BR Apt in Skokie near Leisure Center, holiday rental in Winnetka
DVN Fascinating 1BR Apt in Skokie near Leisure Center, holiday rental in Winnetka
DVN Fascinating 1BR Apt in Skokie near Leisure Center, holiday rental in Winnetka

DVN Fascinating 1BR Apt in Skokie near Leisure Center

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Parking, Private Balcony Near Universities, NAPA, Ravinia & Train to Chicago, holiday rental in Winnetka
Parking, Private Balcony Near Universities, NAPA, Ravinia & Train to Chicago, holiday rental in Winnetka
Parking, Private Balcony Near Universities, NAPA, Ravinia & Train to Chicago, holiday rental in Winnetka

Parking, Private Balcony Near Universities, NAPA, Ravinia & Train to Chicago

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Evanston Garden apt 1bed, two blocks to shopping, dining, bus line for trains, holiday rental in Winnetka
Evanston Garden apt 1bed, two blocks to shopping, dining, bus line for trains, holiday rental in Winnetka
Evanston Garden apt 1bed, two blocks to shopping, dining, bus line for trains, holiday rental in Winnetka

Evanston Garden apt 1bed, two blocks to shopping, dining, bus line for trains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ideal Evanston 1BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Ideal Evanston 1BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Ideal Evanston 1BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka

Ideal Evanston 1BR, 1 mile from Northwestern campus, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Unique Apt. in Upscale Evanston with Easy Access  to Chicago, holiday rental in Winnetka
Unique Apt. in Upscale Evanston with Easy Access  to Chicago, holiday rental in Winnetka
Unique Apt. in Upscale Evanston with Easy Access  to Chicago, holiday rental in Winnetka

Unique Apt. in Upscale Evanston with Easy Access to Chicago

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Serene Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground, holiday rental in Winnetka
Serene Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground, holiday rental in Winnetka
Serene Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground, holiday rental in Winnetka

Serene Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Bright Evanston 1BR, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Bright Evanston 1BR, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Bright Evanston 1BR, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka

Bright Evanston 1BR, 1 mile to Northwestern campus, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Stellar Evanston 1BR w/ Courtyard, nr Beach & University, by Blueground, holiday rental in Winnetka
Stellar Evanston 1BR w/ Courtyard, nr Beach & University, by Blueground, holiday rental in Winnetka
Stellar Evanston 1BR w/ Courtyard, nr Beach & University, by Blueground, holiday rental in Winnetka

Stellar Evanston 1BR w/ Courtyard, nr Beach & University, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sleek Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground, holiday rental in Winnetka
Sleek Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground, holiday rental in Winnetka
Sleek Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground, holiday rental in Winnetka

Sleek Evanston 1BR w/ Dishwasher, walk to Northwestern, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Superb Evanston 1BR w/ Courtyard & W/D, nr Beach, by Blueground, holiday rental in Winnetka
Superb Evanston 1BR w/ Courtyard & W/D, nr Beach, by Blueground, holiday rental in Winnetka
Superb Evanston 1BR w/ Courtyard & W/D, nr Beach, by Blueground, holiday rental in Winnetka

Superb Evanston 1BR w/ Courtyard & W/D, nr Beach, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Fantastic Evanston 1BR w/ Courtyard, nr Northwestern Beach, by Blueground, holiday rental in Winnetka
Fantastic Evanston 1BR w/ Courtyard, nr Northwestern Beach, by Blueground, holiday rental in Winnetka
Fantastic Evanston 1BR w/ Courtyard, nr Northwestern Beach, by Blueground, holiday rental in Winnetka

Fantastic Evanston 1BR w/ Courtyard, nr Northwestern Beach, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Bright, Pet Friendly Home in Family Friendly Neighborhood, holiday rental in Winnetka
Bright, Pet Friendly Home in Family Friendly Neighborhood, holiday rental in Winnetka
Bright, Pet Friendly Home in Family Friendly Neighborhood, holiday rental in Winnetka

Bright, Pet Friendly Home in Family Friendly Neighborhood

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood, holiday rental in Winnetka
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood, holiday rental in Winnetka
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood, holiday rental in Winnetka

Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Elegant Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Elegant Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Elegant Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka

Elegant Evanston 2BR, 1 mile from Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Sunny Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Sunny Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Sunny Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka

Sunny Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Cozy Emerson House 13 miles away from downtown, holiday rental in Winnetka
Cozy Emerson House 13 miles away from downtown, holiday rental in Winnetka
Cozy Emerson House 13 miles away from downtown, holiday rental in Winnetka

Cozy Emerson House 13 miles away from downtown

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Check-out
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Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago, holiday rental in Winnetka
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago, holiday rental in Winnetka
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago, holiday rental in Winnetka

Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
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Bright Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Bright Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Bright Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka

Bright Evanston 2BR, 1 mile from Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Amazing Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Amazing Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Amazing Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka

Amazing Evanston 2BR, 1 mile from Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
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Bright Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Bright Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Bright Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka

Bright Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Sunny Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Sunny Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka
Sunny Evanston 2BR, 1 mile from Northwestern campus, by Blueground, holiday rental in Winnetka

Sunny Evanston 2BR, 1 mile from Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Roomy Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Roomy Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka
Roomy Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground, holiday rental in Winnetka

Roomy Evanston 2BR w/ W/D, 1 mile to Northwestern campus, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden, holiday rental in Winnetka
Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden, holiday rental in Winnetka
Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden, holiday rental in Winnetka

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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Stylish Evanston 2BR w/ Courtyard, nr Northwestern Beach, by Blueground, holiday rental in Winnetka
Stylish Evanston 2BR w/ Courtyard, nr Northwestern Beach, by Blueground, holiday rental in Winnetka
Stylish Evanston 2BR w/ Courtyard, nr Northwestern Beach, by Blueground, holiday rental in Winnetka

Stylish Evanston 2BR w/ Courtyard, nr Northwestern Beach, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lovely Evanston 2BR w/ Courtyard, nr Northwestern & Beach, by Blueground, holiday rental in Winnetka
Lovely Evanston 2BR w/ Courtyard, nr Northwestern & Beach, by Blueground, holiday rental in Winnetka
Lovely Evanston 2BR w/ Courtyard, nr Northwestern & Beach, by Blueground, holiday rental in Winnetka

Lovely Evanston 2BR w/ Courtyard, nr Northwestern & Beach, by Blueground

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago, holiday rental in Winnetka
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago, holiday rental in Winnetka
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago, holiday rental in Winnetka

Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Evanston 2bed+ofc.Walk to sushi, shopping, train & Lake. Minutes to Ryan Field., holiday rental in Winnetka
Evanston 2bed+ofc.Walk to sushi, shopping, train & Lake. Minutes to Ryan Field., holiday rental in Winnetka
Evanston 2bed+ofc.Walk to sushi, shopping, train & Lake. Minutes to Ryan Field., holiday rental in Winnetka

Evanston 2bed+ofc.Walk to sushi, shopping, train & Lake. Minutes to Ryan Field.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Sleepy Sanctuary, holiday rental in Winnetka
Sleepy Sanctuary, holiday rental in Winnetka
Sleepy Sanctuary, holiday rental in Winnetka

Sleepy Sanctuary

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming Convenient Wilmette Home, holiday rental in Winnetka
Charming Convenient Wilmette Home, holiday rental in Winnetka
Charming Convenient Wilmette Home, holiday rental in Winnetka

Charming Convenient Wilmette Home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spacious Townhouse in Wilmette near lake and NW, holiday rental in Winnetka
Spacious Townhouse in Wilmette near lake and NW, holiday rental in Winnetka
Spacious Townhouse in Wilmette near lake and NW, holiday rental in Winnetka

Spacious Townhouse in Wilmette near lake and NW

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite, holiday rental in Winnetka
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite, holiday rental in Winnetka
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite, holiday rental in Winnetka

"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Mid Century Elegance in Evanston Vintage Apartment., holiday rental in Winnetka
Mid Century Elegance in Evanston Vintage Apartment., holiday rental in Winnetka
Mid Century Elegance in Evanston Vintage Apartment., holiday rental in Winnetka

Mid Century Elegance in Evanston Vintage Apartment.

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Northbrook Rental, holiday rental in Winnetka
Northbrook Rental, holiday rental in Winnetka
Northbrook Rental, holiday rental in Winnetka

Northbrook Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Chicago North Shore Close to NWU + Downtown + Beach + Restaurants + Train, holiday rental in Winnetka
Chicago North Shore Close to NWU + Downtown + Beach + Restaurants + Train, holiday rental in Winnetka
Chicago North Shore Close to NWU + Downtown + Beach + Restaurants + Train, holiday rental in Winnetka

Chicago North Shore Close to NWU + Downtown + Beach + Restaurants + Train

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Extended Stay Northbrook FHS Rental, holiday rental in Winnetka
Extended Stay Northbrook FHS Rental, holiday rental in Winnetka
Extended Stay Northbrook FHS Rental, holiday rental in Winnetka

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 Winnetka
Northbrook FHS Rental, holiday rental in Winnetka
Northbrook FHS Rental, holiday rental in Winnetka

Northbrook FHS Rental

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
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Great Hideaway in plain sight, holiday rental in Winnetka
Great Hideaway in plain sight, holiday rental in Winnetka
Great Hideaway in plain sight, holiday rental in Winnetka

Great Hideaway in plain sight

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern Luxury 3 bd Home min from NU & Lake Mich, holiday rental in Winnetka
Modern Luxury 3 bd Home min from NU & Lake Mich, holiday rental in Winnetka
Modern Luxury 3 bd Home min from NU & Lake Mich, holiday rental in Winnetka

Modern Luxury 3 bd Home min from NU & Lake Mich

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Family Apartment w/ Deck + Yard Near Northwestern, holiday rental in Winnetka
Family Apartment w/ Deck + Yard Near Northwestern, holiday rental in Winnetka
Family Apartment w/ Deck + Yard Near Northwestern, holiday rental in Winnetka

Family Apartment w/ Deck + Yard Near Northwestern

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!, holiday rental in Winnetka
Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!, holiday rental in Winnetka
Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!, holiday rental in Winnetka

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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Cozy Old Chicago - 4 Bedroom, holiday rental in Winnetka
Cozy Old Chicago - 4 Bedroom, holiday rental in Winnetka
Cozy Old Chicago - 4 Bedroom, holiday rental in Winnetka

Cozy Old Chicago - 4 Bedroom

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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North Shore 4 bedroom home near New Trier Schools, holiday rental in Winnetka
North Shore 4 bedroom home near New Trier Schools, holiday rental in Winnetka
North Shore 4 bedroom home near New Trier Schools, holiday rental in Winnetka

North Shore 4 bedroom home near New Trier Schools

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spacious family home near Northwestern U, Lake Michigan, holiday rental in Winnetka
Spacious family home near Northwestern U, Lake Michigan, holiday rental in Winnetka
Spacious family home near Northwestern U, Lake Michigan, holiday rental in Winnetka

Spacious family home near Northwestern U, Lake Michigan

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful spacious Evanston home, holiday rental in Winnetka
Beautiful spacious Evanston home, holiday rental in Winnetka
Beautiful spacious Evanston home, holiday rental in Winnetka

Beautiful spacious Evanston home

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Winnetka