Shorewood Holiday Homes
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Holiday Homes in Shorewood

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Our top choices for Shorewood holiday homes

A modern living room with a sofa set, a coffee table, and a rug.

A compact kitchen with dark blue cabinets, a white refrigerator, a microwave, and a stove. There are two wooden chairs and a small wooden table.

A bedroom with a large bed, a nightstand with a lamp, a potted plant, and a mirror.

1. Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Plainfield

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Great host and the home location is awesome for hosting family. "

Yolanda P.

The price is AU$668

AU$668

includes taxes & fees

18 Oct - 19 Oct

Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

A log cabin with a wooden door, two windows, and a sign that reads 'Little House in the Big Woods.'

A modern living room with a sofa, coffee table, and decorative pillows. There is a painting of a bear on the wall and a poster of a park.

A kitchen with wooden cabinets, a stainless steel refrigerator, a white countertop, and a black pot.

2. Travelers Retreat/King Beds/Game Room/Play House

Travelers Retreat/King Beds/Game Room/Play House

Joliet

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great place to stay"

Ken B.

The price is AU$694

AU$694

includes taxes & fees

18 Oct - 19 Oct

Travelers Retreat/King Beds/Game Room/Play House

A sunroom with white walls, wooden flooring, two blue armchairs, a small table with books, and hanging plants.

A living room with two grey sofas, a wooden coffee table, and a staircase leading to an upper floor.

A bedroom with a bed, a TV, a painting, and a window.

3. The Heron House, King Bed Suite, Spacious Remodeled House

The Heron House, King Bed Suite, *Spacious Remodeled House*

Joliet

10.0 out of 10, Exceptional, (55 reviews)

10/10

Exceptional

(55 reviews)

"This is a very clean and well appointed house with good parking. The owner was responsive to our requests"

Nancy H.

The price is AU$648

AU$648

includes taxes & fees

15 Nov - 16 Nov

The Heron House, King Bed Suite, *Spacious Remodeled House*

A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

A dining room with a wooden table set for six, surrounded by black chairs.

A two-story house with a front porch, a garage, and a driveway.

A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

4. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Perfect spot for our group of 6! More than enough dishes/silverware etc. the house was clean and comfortable. Would definitely stay again if in the area."

Kathy L.

The price is AU$736

AU$736

includes taxes & fees

20 Oct - 21 Oct

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

A modern kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large island with a stove.

A dining area with a long table, white chairs, and a decorative runner.

A spacious living area with a stone fireplace, a flat-screen TV mounted above it, and a dining area with a Christmas tree.

A dining area with a dark wooden table, white chairs, and a chandelier. There is a kitchen in the background with white cabinets and a countertop.

5. River Access•Game room•Backyard•King•W/D•Parking

River Access•Game room•Backyard•King•W/D•Parking

Yorkville

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Absolutely loved this place. The backyard was amazing and the house was clean and had everything we needed."

Daniela M.

The price is AU$558

AU$558

includes taxes & fees

19 Oct - 20 Oct

River Access•Game room•Backyard•King•W/D•Parking

(OUTDOOR SPACE) Where comfort and charm come together. Unwind in the outdoor lounge set under an inviting gazebo with twinkling lights. Stay fresh with a gentle breeze from the fan as you relax.

A living room with a fireplace, a sofa, two side tables, and a coffee table.

A bedroom with a large bed, a ceiling fan, a window with curtains, and a door leading to another room.

A modern kitchen with white cabinets, stainless steel appliances, and a central island.

6. 30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

Plainfield

9.4 out of 10, Exceptional, (18 reviews)

9.4/10

Exceptional

(18 reviews)

"Great place to stay."

Taylor E.

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

A living room with a fireplace, a television, a ceiling fan, and a patterned rug.

A kitchen with a stainless steel refrigerator, gray cabinets, a white door, and a black stove.

A dining room with a table, chairs, a chandelier, framed pictures, and a window with curtains.

A living room with a ceiling fan, a patterned rug, a brown leather sofa, and a door with a stained glass window.

7. Verbena Executive Cottage

Verbena Executive Cottage

Morris

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Great host...very clean house."

Kim A.

The price is AU$388

AU$388

includes taxes & fees

18 Oct - 19 Oct

Verbena Executive Cottage

A large, elegant house with a swimming pool, a covered patio, and a grand staircase leading to the entrance.

A large, two-story house with a swimming pool, outdoor seating, and a well-maintained lawn.

A large estate with a swimming pool, a tennis court, and a well-maintained lawn.

A spacious foyer with a grand staircase, a piano, and a seating area with a chandelier.

8. 12,000 SF Mansion w/Pool & Lakeview

12,000 SF Mansion w/Pool & Lakeview

Morris

9.0 out of 10, Wonderful, (11 reviews)

9.0/10

Wonderful

(11 reviews)

"We enjoyed everything."

Yolanda R.

The price is AU$1,675

AU$1,675

includes taxes & fees

18 Oct - 19 Oct

12,000 SF Mansion w/Pool & Lakeview

A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

A backyard with a metal table and chairs, a grill, and a wooden fence.

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a table and chairs.

A dining room with a round table, six chairs, a chandelier, and a view through a window with curtains.

9. PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

Aurora

9.2 out of 10, Wonderful, (15 reviews)

9.2/10

Wonderful

(15 reviews)

"The beds were super comfortable and the location for Naperville/Aurora/Wheaton activities was ideal--about 10 minutes or so for everything."

Scott D.

The price is AU$490

AU$490

includes taxes & fees

18 Oct - 19 Oct

PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

An aerial view of a residential area with a central house featuring a sloped roof, surrounded by trees and a small body of water.

A spacious dining area with a wooden table and chairs, a fruit bowl, and a view into the kitchen.

A spacious dining area with a round wooden table, multiple chairs, and a ceiling fan.

A bedroom with a large bed, two ceiling fans, a wardrobe, a sliding glass door to a balcony, and a built-in bench.

10. Lakeside Channel Hideaway – 4BR/2BA on Goose Lake, Sleeps 10

Lakeside Channel Hideaway – 4BR/2BA on Goose Lake, Sleeps 10

Morris

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Amazing place. Our family group of 9 slept comfortably and had plenty of space to lounge for the holidays. Super clean, awesome water pressure in the shower, will definitely stay again!"

Anonymous traveller

The price is AU$593

AU$593

includes taxes & fees

22 Oct - 23 Oct

Lakeside Channel Hideaway – 4BR/2BA on Goose Lake, Sleeps 10

A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

A bedroom with a large bed, a bedside table, a mirror, and a window.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden floor.

A modern kitchen with white cabinets, a black oven, and a microwave. There is a dining area with a table and chairs.

11. Entire home in Lockport, Illinois

Entire home in Lockport, Illinois

Lockport

8.8 out of 10, Excellent, (5 reviews)

8.8/10

Excellent

(5 reviews)

"The house is very clean. The host was very kind and responsive. "

Susan B.

The price is AU$599

AU$599

includes taxes & fees

27 Oct - 28 Oct

Entire home in Lockport, Illinois

A room with a large bed, a sun-shaped wall decoration, and a television on the wall.

A bedroom with a bed, a potted plant, and a staircase.

A modern kitchen with a dining area, wooden flooring, and a flat-screen TV mounted above the fireplace.

A wooden staircase with a handrail leading to a landing.

12. Spacious 7-bedroom house with AC in wonderful Naperville

Spacious 7-bedroom house with AC in wonderful Naperville

Naperville

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"Very smooth booking, checking in, and checking out process. The house was older, and it showed, but was big enough to hold my group. There were problems with the fire detectors randomly beeping, and some mold in the basement, but everything else was fine."

Brett H.

The price is AU$1,575

AU$1,575

includes taxes & fees

19 Oct - 20 Oct

Spacious 7-bedroom house with AC in wonderful Naperville

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

A hallway with wooden flooring, white walls, and doors leading to rooms.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining table with chairs.

A living room with a sofa, a coffee table, a TV, and a floor lamp.

13. Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

Aurora

7.4 out of 10, Good, (3 reviews)

7.4/10

Good

(3 reviews)

"Overall good I would stay there again if I was to travel to Chicago again"

Avo H.

The price is AU$519

AU$519

includes taxes & fees

2 Nov - 3 Nov

Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

A bedroom with a bed, a ceiling fan, two wall-mounted lights, a window with curtains, and a wooden dresser.

A dining room with a wooden table and chairs, large windows with blinds, and a black pendant light.

A modern kitchen with large windows, a dining area with wicker chairs, and stainless steel appliances.

14. 4BR Tudor • Wooded Lot • 10 Min to Downtown

4BR Tudor • Wooded Lot • 10 Min to Downtown

Naperville

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"This is a spacious house in a very nice, quiet neighborhood. The backyard is a perfect spot to relax and soak in the sun/play games. This is a great house for families. We had a nearby wedding and this was a wonderful house to get ready at. The hosts are extremely welcoming and communicate wonderfully. "

Alicia F.

The price is AU$891

AU$891

includes taxes & fees

16 Nov - 17 Nov

4BR Tudor • Wooded Lot • 10 Min to Downtown

A living room with a large window, a sofa, a chair, and a desk with a vase of flowers.

An outdoor patio with a ceiling fan, a glass door leading to a covered area, and a seating arrangement with a table and chairs.

A bedroom with a bed, a bedside table with a lamp, a clock, and a window with curtains.

A ping pong table with a ball and paddle in the foreground, a sofa with cushions in the background, and a wall with framed pictures.

15. Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

Naperville

The price is AU$718

AU$718

includes taxes & fees

21 Oct - 22 Oct

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with seating.

A living room with a stone fireplace, a leather couch, and various decorations including a deer head and antlers.

A single-story house with a garage, a front lawn, and a large tree.

A dining area with a table set for six, surrounded by chairs, a chandelier, and artwork on the walls.

16. 4 bedroom country house in Morris

4 bedroom country house in Morris

Morris

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Host was great, property was clean and well kempt."

Brandon H.

The price is AU$742

AU$742

includes taxes & fees

19 Oct - 20 Oct

4 bedroom country house in Morris

Immediately feel at home when you step into the grand entryway.

A spacious kitchen with wooden beams, a large island with stools, and a dining area with a table and chairs.

A spacious kitchen with a large island, wooden cabinets, and a modern pendant light.

A modern kitchen with wooden cabinets, a large island, and a skylight.

17. 2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

Plano

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"This is our second year in a row for our annual Friendsgiving. We love the place and plan to make it our annual house for our group! "

Aaron P.

The price is AU$1,681

AU$1,681

includes taxes & fees

21 Oct - 22 Oct

2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

A backyard with a fire pit, four Adirondack chairs, and a house in the background.

A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a coffee bar.

A bedroom with a wooden bed, white bedding, and a cityscape wall art.

18. River Park Paradise w/ Fire Pit & Chef's Kitchen

River Park Paradise w/ Fire Pit & Chef's Kitchen

Bolingbrook

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Excellent just what we were looking for"

Sue B.

The price is AU$1,246

AU$1,246

includes taxes & fees

18 Oct - 19 Oct

River Park Paradise w/ Fire Pit & Chef's Kitchen

A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

A spacious living area with a round dining table, multiple chairs, a sofa, and a TV.

A living room with a glass coffee table, leather sofa, and a red accent wall.

19. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Lisle

9.4 out of 10, Exceptional, (36 reviews)

9.4/10

Exceptional

(36 reviews)

"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "

Ella A.

The price is AU$496

AU$496

includes taxes & fees

19 Oct - 20 Oct

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

A patio area with outdoor furniture, a gazebo, and a barbecue grill.

A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

A spacious living room with a gray sofa, a coffee table, a black entertainment unit, and a large painting on the wall.

A rural landscape with a pond reflecting trees and a wooden structure.

20. Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Aurora

10.0 out of 10, Exceptional, (35 reviews)

10/10

Exceptional

(35 reviews)

"The property was perfect for our family! There was plenty of room, indoors and out, for us, our kids, and our grandkids. The house was spotless and the kitchen was extensively stocked with dishes, cookware, etc. We also appreciated the numerous comfy places to gather."

Mila M.

The price is AU$1,633

AU$1,633

includes taxes & fees

19 Oct - 20 Oct

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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