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

Maywood Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
$283 nightly
The price is $302
Oct 19 - Oct 20
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
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
$206 nightly
The price is $236
Oct 26 - Oct 27
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.
$262 nightly
The price is $300
Oct 26 - Oct 27
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
Private kitchen

4. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
$224 nightly
The price is $256
Oct 27 - Oct 28
Total with taxes and fees
1BR Apartment - Walk to Shops - Downtown OAK PARK
A glass elevator with a city view.

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.
$255 nightly
The price is $292
Oct 27 - Oct 28
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern living room with teal sofas, a coffee table, and a TV.

6. 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, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
$150 nightly
The price is $160
Oct 18 - Oct 19
Total with taxes and fees
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

7. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$294 nightly
The price is $337
Oct 27 - Oct 28
Total with taxes and fees
The Oak Park Loft
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

8. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
$276 nightly
The price is $316
Oct 27 - Oct 28
Total with taxes and fees
Historic Oak Park Home
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

9. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
$478 nightly
The price is $512
Oct 20 - Oct 21
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A two-story house with a visible front porch and a large evergreen tree in the foreground.

10. First floor of Historic Oak Park Villa, Grge:2Cars

First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
$310 nightly
The price is $355
Oct 27 - Oct 28
Total with taxes and fees
First floor of Historic Oak Park Villa, Grge:2Cars
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.

11. 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
$324 nightly
The price is $400
Oct 19 - Oct 20
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A modern living room with a sectional sofa, a coffee table, and a TV.

12. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
$205 nightly
The price is $235
Oct 19 - Oct 20
Total with taxes and fees
Attractive Coach House Apartment for rent in Oak Park.
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
$348 nightly
The price is $372
Oct 26 - Oct 27
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

14. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
$243 nightly
The price is $287
Nov 2 - Nov 3
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
A white two-story house with a porch, steps, and a small table with chairs.

15. 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.
$581 nightly
The price is $665
Nov 1 - Nov 2
Total with taxes and fees
Oak Park Victorian by FLW Studio
A bedroom with a bed, bedside tables, a ceiling fan, a window with curtains, and a radiator.

16. Top floor of Historic Oak Park Home /2 Car Garage

Top floor of Historic Oak Park Home /2 Car Garage
Oak Park
9.6 out of 10, Exceptional, (24 reviews)
"Our stay was wonderful. The location with parking was perfect."
United States
Joan W.
$352 nightly
The price is $400
Oct 25 - Oct 26
Total with taxes and fees
Top floor of Historic Oak Park Home /2 Car Garage
Terrace/patio

17. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
$310 nightly
The price is $355
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
A living room with a grey sofa, a white coffee table, and a grey rug.

18. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (25 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
$219 nightly
The price is $234
Nov 2 - Nov 3
Total with taxes and fees
Small hidden Gem. Location!
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

19. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.0 out of 10, Wonderful, (9 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$304 nightly
The price is $360
Oct 28 - Oct 29
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

20. 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
$667 nightly
The price is $811
Oct 26 - Oct 27
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Maywood Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Nice enough room on the small side with tight bathroom. Small lobby. It is what it is. Convenient location. No real complaints"
Joseph 1-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile

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 $81 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.