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Bolingbrook Holiday Rentals

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42 rentals in Bolingbrook.
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Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping, holiday rental in Bolingbrook

Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping

4 bedrooms
4 bathrooms
Sleeps 16
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Winding Meadows Home Away from Home, holiday rental in Bolingbrook

Winding Meadows Home Away from Home

2 bedrooms
2 bathrooms
Sleeps 4
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Professionally Sanitized - Downtown Naperville - Three Bedroom Retreat, holiday rental in Bolingbrook

Professionally Sanitized - Downtown Naperville - Three Bedroom Retreat

3 bedrooms
2 bathrooms
Sleeps 10
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Large, sunny 3 bedroom apartment two blocks from down town Oak Park., holiday rental in Bolingbrook

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

3 bedrooms
1 bathroom
Sleeps 8
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'St Geneva' Private With River View!, holiday rental in Bolingbrook

'St Geneva' Private With River View!

3 bedrooms
1 bathroom
Sleeps 5
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Executive Home with All the Amenities, holiday rental in Bolingbrook

Executive Home with All the Amenities

4 bedrooms
5 bathrooms
Sleeps 10
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Entire House! Sleeps 8-Cozy, Clean & Well-Stocked, holiday rental in Bolingbrook

Entire House! Sleeps 8-Cozy, Clean & Well-Stocked

3 bedrooms
2 bathrooms
Sleeps 8
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Ideal Naperville Neighborhood Getaway, holiday rental in Bolingbrook

Ideal Naperville Neighborhood Getaway

4 bedrooms
3 bathrooms
Sleeps 10
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Adorable home near downtown Wheaton no up-charge for additional guests, holiday rental in Bolingbrook

Adorable home near downtown Wheaton no up-charge for additional guests

4 bedrooms
2 bathrooms
Sleeps 8
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Close to Everything - Naperville!, holiday rental in Bolingbrook

Close to Everything - Naperville!

3 bedrooms
3 bathrooms
Sleeps 8
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Spacious and comfortable 5 bedroom, 2 1/2 bath two miles from down town Geneva, holiday rental in Bolingbrook

Spacious and comfortable 5 bedroom, 2 1/2 bath two miles from down town Geneva

5 bedrooms
3 bathrooms
Sleeps 8
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The Davis House, Landmarked 1892 Farm House, holiday rental in Bolingbrook

The Davis House, Landmarked 1892 Farm House

3 bedrooms
3 bathrooms
Sleeps 8
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Professionally Sanitized - Dome Away From Home - Secluded Naperville Retreat, holiday rental in Bolingbrook

Professionally Sanitized - Dome Away From Home - Secluded Naperville Retreat

3 bedrooms
2 bathrooms
Sleeps 11
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Historic Downtown Naperville, holiday rental in Bolingbrook

Historic Downtown Naperville

5 bedrooms
3 bathrooms
Sleeps 10
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In Town Apartment in downtown Geneva!!, holiday rental in Bolingbrook

In Town Apartment in downtown Geneva!!

2 bedrooms
1 bathroom
Sleeps 6
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Perfect Getaway_Kayak_Hiking_Waterpark_FastWiFi, holiday rental in Bolingbrook

Perfect Getaway_Kayak_Hiking_Waterpark_FastWiFi

2 bedrooms
2 bathrooms
Sleeps 6
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Sunny Jumbo Studio in the Heart of Oak Park, holiday rental in Bolingbrook

Sunny Jumbo Studio in the Heart of Oak Park

1 bedroom
1 bathroom
Sleeps 2
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5Bedroom Home in Homer Glen, holiday rental in Bolingbrook

5Bedroom Home in Homer Glen

5 bedrooms
3 bathrooms
Sleeps 10
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New&Modern Apartment only 4 miles away from Midway, holiday rental in Bolingbrook

New&Modern Apartment only 4 miles away from Midway

3 bedrooms
2 bathrooms
Sleeps 8
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Cozy Cabin In Roselle, holiday rental in Bolingbrook

Cozy Cabin In Roselle

1 bedroom
1 bathroom
Sleeps 2
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Professionally Sanitized - Downtown Naperville 4.5 Bedroom Farmhouse, holiday rental in Bolingbrook

Professionally Sanitized - Downtown Naperville 4.5 Bedroom Farmhouse

4 bedrooms
2 bathrooms
Sleeps 9
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Upscale Condo, Washer and Dryer, Fireplace, King Bed, Close To It All, holiday rental in Bolingbrook

Upscale Condo, Washer and Dryer, Fireplace, King Bed, Close To It All

1 bedroom
1 bathroom
Sleeps 4
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Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!, holiday rental in Bolingbrook

Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!

4 bedrooms
1 bathroom
Sleeps 5
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Upscale Suburban Neighborhood, holiday rental in Bolingbrook

Upscale Suburban Neighborhood

1 bedroom
1 bathroom
Sleeps 3
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Oak Park Beauty Sleeps 1 to 8 Guests, holiday rental in Bolingbrook

Oak Park Beauty Sleeps 1 to 8 Guests

3 bedrooms
1 bathroom
Sleeps 6
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Upscale Condo Near Downtown, Highways, Dining, Shopping, Free Parking, Fireplace, holiday rental in Bolingbrook

Upscale Condo Near Downtown, Highways, Dining, Shopping, Free Parking, Fireplace

1 bedroom
1 bathroom
Sleeps 4
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Upscale Suburban Neighborhood, holiday rental in Bolingbrook

Upscale Suburban Neighborhood

1 bedroom
1 bathroom
Sleeps 2
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Upscale Suburban Neighborhood, holiday rental in Bolingbrook

Upscale Suburban Neighborhood

1 bedroom
1 bathroom
Sleeps 2
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Make It Your Own - 15 Minutes to Chicago, holiday rental in Bolingbrook

Make It Your Own - 15 Minutes to Chicago

1 bedroom
1 bathroom
Sleeps 4
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Condo, holiday rental in Bolingbrook

Condo

2 bedrooms
2 bathrooms
Sleeps 4
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Heart of Oak Park, train ride to downtown Chicago.  WIFI & Cable Included!, holiday rental in Bolingbrook

Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!

2 bedrooms
1 bathroom
Sleeps 5
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Oak Park's Historic Getaway w/FHS, holiday rental in Bolingbrook

Oak Park's Historic Getaway w/FHS

3 bedrooms
2 bathrooms
Sleeps 8
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Modern and comfortable apartment, holiday rental in Bolingbrook

Modern and comfortable apartment

1 bedroom
1 bathroom
Sleeps 4
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QUIET 4 BEDROOM HOME ON A CUL DE SAC, holiday rental in Bolingbrook

QUIET 4 BEDROOM HOME ON A CUL DE SAC

4 bedrooms
4 bathrooms
Sleeps 8
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Charming Downtown Naperville Farmhouse - 1 Bedroom Guest Suite - Walk to Town, holiday rental in Bolingbrook

Charming Downtown Naperville Farmhouse - 1 Bedroom Guest Suite - Walk to Town

1 bedroom
1 bathroom
Sleeps 2
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Oswego Townhouse, holiday rental in Bolingbrook

Oswego Townhouse

2 bedrooms
1 bathroom
Sleeps 4
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Executive Home with All the Amenities, holiday rental in Bolingbrook

Executive Home with All the Amenities

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Clean and Refreshing Home Sweet Home, holiday rental in Bolingbrook

Clean and Refreshing Home Sweet Home

2 bedrooms
1 bathroom
Sleeps 5
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Fully-Equipped Suite | Free Weekday Shuttle + Gym Access, holiday rental in Bolingbrook

Fully-Equipped Suite | Free Weekday Shuttle + Gym Access

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Lemont Valley Estate - BREATHTAKING views, holiday rental in Bolingbrook

Lemont Valley Estate - BREATHTAKING views

8 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Cozy, Quiet and Relaxing Space, holiday rental in Bolingbrook

Cozy, Quiet and Relaxing Space

3 bedrooms
1 bathroom
Sleeps 5
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Cheerful three bedroom, 2 full bath in oak Forest, holiday rental in Bolingbrook

Cheerful three bedroom, 2 full bath in oak Forest

3 bedrooms
2 bathrooms
Sleeps 6
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