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

Maywood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Maywood vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,328 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is AED 559
AED 764 total
includes taxes & fees
27 Sep - 28 Sep
Sentral Michigan Avenue
Breakfast, lunch and dinner served

2. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (263 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is AED 686
AED 785 total
includes taxes & fees
28 Sep - 29 Sep
The Gem Museum Suites
Living area

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.0 out of 10, Very good, (56 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is AED 559
AED 656 total
includes taxes & fees
22 Sep - 23 Sep
Wrigleyville Suites
Apartment, Private Bathroom | Lounge

4. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is AED 736
AED 1,251 total
includes taxes & fees
6 Oct - 7 Oct
At Home in Oak Park
Full-size fridge, microwave, oven, stovetop

5. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (527 reviews)
"Location and facility was very nice"
United States
Brian
The price is AED 1,091
AED 1,371 total
includes taxes & fees
28 Sep - 29 Sep
Level Chicago – Old Town
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

6. 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
The price is AED 803
AED 1,327 total
includes taxes & fees
14 Oct - 15 Oct
Historic Oak Park Home
Lake

7. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (35 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
The price is AED 3,193
AED 4,320 total
includes taxes & fees
1 Oct - 2 Oct
Kasa Lake Shore Chicago
House (3 Bedrooms) | Interior

8. 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 AED 889
AED 1,744 total
includes taxes & fees
22 Sep - 23 Sep
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

9. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is AED 981
AED 1,531 total
includes taxes & fees
23 Sep - 24 Sep
Historic Oak Park Residence
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

10. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is AED 652
AED 1,155 total
includes taxes & fees
13 Oct - 14 Oct
The Oak Park Loft
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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"Elevators not all working and could not get heat in the room over a rainy and cool weekend"
Sandra 3-night trip
Posted less than an hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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 7 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.