A city skyline with a prominent skyscraper, a marina with boats, and a river.

Maywood Vacation Rentals

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Check prices for these dates

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

Our top choices for Maywood vacation 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.
$270 nightly
The price is $288
Nov 16 - Nov 17
Total with taxes and fees
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
$189 nightly
The price is $216
Nov 17 - Nov 18
Total with taxes and fees
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.
$236 nightly
The price is $270
Nov 10 - Nov 11
Total with taxes and fees
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.
$202 nightly
The price is $232
Nov 17 - Nov 18
Total with taxes and fees
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
$444 nightly
The price is $475
Nov 9 - Nov 10
Total with taxes and fees
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.
$164 nightly
The price is $175
Nov 8 - Nov 9
Total with taxes and fees
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
$313 nightly
The price is $386
Nov 18 - Nov 19
Total with taxes and fees
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.
$162 nightly
The price is $173
Nov 8 - Nov 9
Total with taxes and fees
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.
$518 nightly
The price is $593
Nov 10 - Nov 11
Total with taxes and fees
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.
$166 nightly
The price is $184
Nov 9 - Nov 10
Total with taxes and fees
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
$535 nightly
The price is $650
Nov 10 - Nov 11
Total with taxes and fees
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 traveler
$316 nightly
The price is $338
Nov 9 - Nov 10
Total with taxes and fees
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.
$281 nightly
The price is $332
Nov 21 - Nov 22
Total with taxes and fees
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, (6 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.
$390 nightly
The price is $458
Nov 9 - Nov 10
Total with taxes and fees
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.
$566 nightly
The price is $631
Nov 9 - Nov 10
Total with taxes and fees
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
$156 nightly
The price is $183
Nov 16 - Nov 17
Total with taxes and fees
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.
$209 nightly
The price is $228
Nov 9 - Nov 10
Total with taxes and fees
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 traveler
$702 nightly
The price is $854
Nov 9 - Nov 10
Total with taxes and fees
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.
$207 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
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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Top Maywood Hotel Reviews

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Nice environment and very reasonable prices..right downtown so great location!"
Ebony 2-night trip
Posted 5 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Find out more about Maywood

Everything you need to know about Maywood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Maywood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Maywood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Maywood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Maywood rentals

At Expedia, we put the best Maywood vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Maywood?

Yes, there are vacation rentals close to top local attractions in Maywood, or you can choose a secluded option if you're looking for relaxation. 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's the top vacation rental that Maywood has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated vacation home rental in Maywood offers a patio, a barbecue grill, 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 vacation rentals will I find in Maywood?

With 6 Expedia vacation rentals, you're sure 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 vacation rental in Maywood like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Maywood. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.