Maywood Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Maywood holiday rentals

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

1. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (35 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AU$417
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

2. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (75 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is AU$310
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

3. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AU$391
includes taxes & fees
10 Nov - 11 Nov
Cozy, Comfortable and Convenient apartment. Close to everything!
A hallway with a wooden floor, a bench, and two abstract paintings on the wall.

4. Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Berwyn
9.4 out of 10, Exceptional, (26 reviews)
"A very comfy older building that has been upgraded in several areas. Convenient to transportation, restaurants and local events. "
United States
Carrie
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
A modern building with a brick facade, large windows, and a central entrance area.

5. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is AU$332
includes taxes & fees
17 Nov - 18 Nov
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

6. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is AU$685
includes taxes & fees
10 Nov - 11 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

7. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is AU$255
includes taxes & fees
8 Nov - 9 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

8. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is AU$558
includes taxes & fees
11 Nov - 12 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A modern living room with teal sofas, a coffee table, and a TV.

9. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (26 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is AU$252
includes taxes & fees
8 Nov - 9 Nov
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A white two-story house with a porch, steps, and a small table with chairs.

10. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is AU$847
includes taxes & fees
10 Nov - 11 Nov
Oak Park Victorian by FLW Studio
A modern living room with a blue sofa, a patterned rug, and a television.

11. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is AU$270
includes taxes & fees
9 Nov - 10 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

12. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AU$863
includes taxes & fees
9 Nov - 10 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

13. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is AU$494
includes taxes & fees
9 Nov - 10 Nov
LUXE 3 BR, 2 BA + Hot Tub
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

14. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
Private Workspace • Sleeps 4 • Modern and Stylish
A modern bedroom with a large bed, white bedding, and a view of a forest through the window.

15. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (7 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
The price is AU$633
includes taxes & fees
9 Nov - 10 Nov
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

16. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is AU$939
includes taxes & fees
9 Nov - 10 Nov
Vibrant House, Walk to Train, Game Room
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

17. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
The price is AU$249
includes taxes & fees
9 Nov - 10 Nov
Wrigleyville Suites
A bedroom with a bed, bedside tables, a mirror, and a door leading to another room.

18. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (8 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is AU$327
includes taxes & fees
9 Nov - 10 Nov
Relaxing 3BR Getaway Close to Dining & Shopping
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is AU$1,221
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A rooftop terrace with a brick wall, large windows, and a metal railing.

20. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is AU$363
includes taxes & fees
9 Nov - 10 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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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Find holiday rentals that suit your style

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Top Maywood Hotel Reviews

A modern lounge area with leather sofas, a coffee table, and a patterned rug.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont

10/10 Excellent

Everything is as it should be
Australia
Kevin
Reviewed July 2, 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG

Find out more about Maywood

Everything you need to know about Maywood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Maywood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Maywood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Maywood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Maywood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Maywood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Maywood holiday rentals we have selected for you start as low as AU$109 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Maywood rentals

At Expedia, we put the best Maywood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Maywood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Maywood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Maywood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Maywood?

Yes, there are holiday rentals close to the most popular sights in Maywood, or you can select a more secluded option if you're looking for a relaxing stay. Maywood is known for its shopping and restaurants. Make sure you have time to check out the festivals while you're in the area.

What are some of the best holiday rentals that Maywood has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated holiday home rental in Maywood offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals will I find in Maywood?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Maywood stay.

What’s there to see and do in Maywood?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. Wrigley Field and Soldier Field are other popular places to visit in the area.

What’s a holiday rental in Maywood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Maywood. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.