Wheeling Vacation Home Rentals from CA $302: Search Top Private Vacation Homes for Rent

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A rustic mill by a calm river, surrounded by autumn foliage and a clear blue sky.

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Our top choices for Wheeling vacation homes

A single-story house with a front door, a small window, and a trash can.

A modern bathroom with a large sink, toilet, and bathtub.

A well-maintained lawn with a house and a paved walkway.

A single-story brick house with a front door, a garage door, and a small front yard with a hedge and a lawn.

1. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard

The price is CA $172

CA $172

CA $540 total

includes taxes & fees

Sep 7 - Sep 8

Lombard 1BR & 1BH Suite Close to freeway & Mall

A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

A room with a desk, a chair, a TV mounted on the wall displaying various streaming services, a window with a blind, and a framed picture on the wall.

A two-story house with a brick exterior, a covered porch, and a stone pathway leading to the entrance.

A large bed with a wooden headboard, two bedside tables with lamps, and a window with a view of trees.

2. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities

Riverwoods

9.8 out of 10, Exceptional, (86 reviews)

9.8/10

Exceptional

(86 reviews)

"Great spot, safe, clean, and beautiful environment would highly recommend!"

Chris F.

The price is CA $161

CA $161

CA $302 total

includes taxes & fees

Sep 20 - Sep 21

Master qtr close to nature & easy urban facilities

A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

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

A hotel room with two beds, a patterned rug, and a painting on the wall.

An outdoor wooden deck with two chairs and a small table, featuring string lights overhead.

3. 6 Kings Ping-Pong Gazebo!

6 Kings Ping-Pong Gazebo!

Northbrook

9.0 out of 10, Wonderful, (7 reviews)

9.0/10

Wonderful

(7 reviews)

"Hosts were great. Very accommodating to our needs and quick to respond. I will stay again!"

Cj Y.

The price is CA $341

CA $341

CA $837 total

includes taxes & fees

Sep 9 - Sep 10

6 Kings Ping-Pong Gazebo!

A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

A two-story house with a white exterior and black trim, a large front window, and a small front porch.

A living room with a black sofa, two white armchairs, a wooden coffee table, and a patterned rug.

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

4. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug

Des Plaines

9.8 out of 10, Exceptional, (23 reviews)

9.8/10

Exceptional

(23 reviews)

"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."

Richie S.

The price is CA $237

CA $237

CA $487 total

includes taxes & fees

Sep 9 - Sep 10

Cozy Home by O'Hare + EV Plug

A dining area with a wooden table set for four, surrounded by grey armchairs. A large abstract painting is on the wall, and a potted plant is visible in the background.

A room with a pool table, a billiards table, a green felt table, and a bar area with chairs and a neon sign.

A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

A modern living room with a green sofa, a wooden coffee table, and a wicker basket.

5. Stylish Escape/Game Room/4 Brs

Stylish Escape/Game Room/4 Brs

Arlington Heights

9.4 out of 10, Exceptional, (16 reviews)

9.4/10

Exceptional

(16 reviews)

"Great place to stay in a great neighborhood."

Sam M.

The price is CA $519

CA $519

CA $1,116 total

includes taxes & fees

Sep 7 - Sep 8

Stylish Escape/Game Room/4 Brs

A two-story house with a stone chimney, a front porch with steps, and a flag.

A dining room with a wooden table, four chairs, a vase with flowers, a chandelier, and a large mirror on the wall.

A kitchen with white cabinets, a wooden dining table with chairs, a stove, and a dishwasher.

A two-story house with a covered patio, a brick exterior, and a wooden fence.

6. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base

Mundelein

9.8 out of 10, Exceptional, (75 reviews)

9.8/10

Exceptional

(75 reviews)

"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"

Jaclyn Z.

The price is CA $187

CA $187

CA $494 total

includes taxes & fees

Sep 8 - Sep 9

Quaint Bungalow, near Great Lakes Naval Base

A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

A modern living room with a sofa, coffee table, and dining area.

A spacious living room with a red sofa set, a coffee table, a wicker side table, and a lamp. There are two windows with blinds, a staircase, and a view of a fence.

A storefront with a striped awning and a sign reading 'Rocky Mountain Chocolate Factory.'

7. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Libertyville

The price is CA $188

CA $188

CA $854 total

includes taxes & fees

Sep 8 - Sep 9

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

A modern kitchen with white cabinets, a black stove, and a microwave.

A modern living room with a dark brown sofa, a coffee table, and a TV mounted on the wall.

A modern entryway with a grey wall, a white door, and a view of a green field through a large window.

A park with a gazebo, trees, and a lake.

8. Your Next Vacation Home

Your Next Vacation Home

Oakton

9.4 out of 10, Exceptional, (82 reviews)

9.4/10

Exceptional

(82 reviews)

"Peaceful and quiet with a great lake to fish and pedal boat on. Clean and a great space for kids!"

Ashley L.

The price is CA $286

CA $286

CA $520 total

includes taxes & fees

Sep 22 - Sep 23

Your Next Vacation Home

A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

A dining area with a wooden table, white chairs, a potted plant, and a ceiling light fixture.

A wooden deck with a wicker chair and a table, a potted plant, and a house in the background.

A modern hotel room with a large bed, bedside tables, a mirror, and a potted plant.

9. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit

Belmont Cragin

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great location, safe and quiet. Perfect for our family of 6!"

Jason

The price is CA $102

CA $102

CA $717 total

includes taxes & fees

Sep 8 - Sep 9

4BR Retreat w/ Theater, Arcade, Gym and Firepit

A modern living room with a sofa, a coffee table, and a view of the outdoors.

A kitchen with a stainless steel stove, four frying pans, a pot, and a digital display.

A modern bedroom with a bed, a grey sofa, and a flat-screen TV on the wall.

A modern living room with a glass coffee table, a bottle of wine, two wine glasses, a potted plant, and a comfortable chair.

10. Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Super comfy for families and the nicest host. "

Anonymous traveller

The price is CA $459

CA $459

CA $812 total

includes taxes & fees

Sep 8 - Sep 9

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

A modern TopGolf facility with a prominent entrance, multiple levels, and a parking area.

A modern living room with two blue armchairs, a wooden coffee table, and a large plant.

A room with a blue sofa, a yellow curtain, and a plant.

A bed with black and white patterned pillows, a black metal headboard, and a view of trees through sheer curtains.

11. Near Chicago&O’Hare/King Bed/WiFi+Game room

Near Chicago&O’Hare/King Bed/WiFi+Game room

Schaumburg

9.6 out of 10, Exceptional, (35 reviews)

9.6/10

Exceptional

(35 reviews)

"Host was amazing, house was clean and easy to access! "

Central A.

The price is CA $273

CA $273

CA $604 total

includes taxes & fees

Sep 7 - Sep 8

Near Chicago&O’Hare/King Bed/WiFi+Game room

A modern living room with a sofa, a round coffee table, a plant, and a view of the city through large windows.

A modern office space with a large meeting table, comfortable seating, and large windows offering a view of the city.

A modern interior with large windows, a wooden floor, and a conference table with chairs.

12. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops

Near North Side

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

The price is CA $491

CA $491

CA $1,028 total

includes taxes & fees

Sep 21 - Sep 22

Modern 3BR Apartment Near North Ave Shops

13. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15

Portage Park

8.8 out of 10, Excellent, (3 reviews)

8.8/10

Excellent

(3 reviews)

"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."

Latasha C.

The price is CA $139

CA $139

CA $972 total

includes taxes & fees

Sep 7 - Sep 8

Arcade • Theater • Gym • Office • Sleeps 15

A patio area with stone flooring, wicker furniture, and a brick building in the background.

A modern living room with a sectional sofa, a small side table, and a chair.

A bedroom with a large bed, a desk, and a chandelier.

14. Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

South Evanston

9.8 out of 10, Exceptional, (43 reviews)

9.8/10

Exceptional

(43 reviews)

"The property was in an excellent location; easy walk to beach, beautiful and quiet neighborhood, easy walk to shops. The apartment was clean and spacious. We enjoyed out stay. Only complaint is no TV. We spent much of our time with my daughter who lives nearby but if I had mornings or longer evenings inside, I would have wanted a TV."

debra

The price is CA $275

CA $275

CA $461 total

includes taxes & fees

Sep 9 - Sep 10

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

A modern kitchen with stainless steel appliances, grey cabinetry, and pendant lighting.

A room with teal upholstered chairs, a metal side table with a vase and a placard reading "LONDON", and abstract paintings on the wall.

A modern kitchen with grey cabinets, a stainless steel refrigerator, and pendant lighting.

A two-story house with a grey exterior, a brown roof, and a front yard with a wooden fence and a small tree.

15. AeroStay Retreat – 4BR Home Near O’Hare Airport!

AeroStay Retreat – 4BR Home Near O’Hare Airport!

Wood Dale

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Large space great for family"

Remona S.

The price is CA $339

CA $339

CA $741 total

includes taxes & fees

Sep 14 - Sep 15

AeroStay Retreat – 4BR Home Near O’Hare Airport!

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

A bedroom with a bed, bedside tables, a closet, and a painting on the wall.

A living room with a brick fireplace, a blue armchair, a brown leather sofa, and a wooden coffee table.

A living room with a brown leather sofa, two blue armchairs, a dark coffee table, and a patterned rug.

16. PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

streamwood

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Was nice would recommend staying with you folks"

Richard W.

The price is CA $280

CA $280

CA $605 total

includes taxes & fees

Sep 13 - Sep 14

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

A modern kitchen with stainless steel appliances, a microwave, and a coffee maker.

17. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Near North Side

9.6 out of 10, Exceptional, (21 reviews)

9.6/10

Exceptional

(21 reviews)

"Very clean, very quite loved having 3 bathrooms, had everything you’d need for your stay"

The price is CA $529

CA $529

CA $1,094 total

includes taxes & fees

Sep 13 - Sep 14

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

A wicker outdoor seating area with a table set for a meal, including fruits and wine glasses.

A modern living room with a fireplace, two white sofas, a coffee table, and a pool table.

18. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard

Belmont Cragin

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."

kim r.

The price is CA $117

CA $117

CA $624 total

includes taxes & fees

Sep 8 - Sep 9

Game Room • Fire-pit • Playground • Gym • Billiard

A modern living room with a sofa, chairs, and a dining area.

A dining area with a round table, four chairs, a vase of flowers, and a chandelier.

A living room with two beige sofas, a glass coffee table, and a large wall painting.

A small, single-story house with a white exterior, a front door, and a large window.

19. Parisian Inspired Escape - Close to Town & NU

Parisian Inspired Escape - Close to Town & NU

Church & Dodge

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The host was very friendly and helpful. It was the perfect space for our long weekend!"

Jenny M.

The price is CA $552

CA $552

CA $985 total

includes taxes & fees

Sep 16 - Sep 17

Parisian Inspired Escape - Close to Town & NU

A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

A room with a black bean bag chair, a small table with a plant, and a tic-tac-toe game on a clear glass table.

A bedroom with a bed, a dresser, a TV on the wall, and a door leading to a bathroom.

A modern living room with a white sofa, a round coffee table, a fireplace, and a flat-screen TV mounted on the wall.

20. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Portage Park

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"

Ashley Y.

The price is CA $143

CA $143

CA $1,158 total

includes taxes & fees

Sep 8 - Sep 9

Sleeps 18 • 8BR • Game Room • Gym • Theater

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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