Maywood Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Maywood holiday rentals

Microwave, oven, stovetop, dishwasher
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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (20)
"Very nice place "
United States
Elliot H.
The price is HK$1,154
HK$1,833 total
includes taxes & fees
29 Dec - 30 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Interior
Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!
Burr Ridge
9.8 out of 10, Exceptional, (35)
"We loved it!!! Perfect space for the 3 of us area is beautiful!! "
United States
Aaliyah G.
The price is HK$804
HK$1,625 total
includes taxes & fees
31 Dec - 1 Jan 2026
Less is more! Pet friendly Tiny Home near Chicago!
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1023)
"My favorite place to stay hands-down"
United States
Michele
The price is HK$918
HK$1,306 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (405)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Business centre
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$536
HK$1,286 total
includes taxes & fees
6 Jan - 7 Jan 2026
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$490
HK$1,309 total
includes taxes & fees
25 Jan - 26 Jan 2026
Sleek 1BR Apt w/ Laundry
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$490
HK$1,309 total
includes taxes & fees
6 Jan - 7 Jan 2026
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$490
HK$1,309 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$490
HK$1,309 total
includes taxes & fees
6 Jan - 7 Jan 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,309 total
includes taxes & fees
8 Jan - 9 Jan 2026
The One: A 1BR Stay That Feels Like Home
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$490
HK$1,309 total
includes taxes & fees
6 Jan - 7 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is HK$1,023
HK$1,201 total
includes taxes & fees
8 Jan - 9 Jan 2026
Chicago luxury home suites
Terrace/patio
River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
River North Private Balcony With In and Out Parking
TV, offices
South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
South Loop Rooftop With In & Out Parking 1
Fridge, microwave, dishwasher, coffee/tea maker
Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
2.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
Modern West Loop Gem-City Views & Prime Location 2
Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is HK$492
HK$1,742 total
includes taxes & fees
30 Dec - 31 Dec
Chicago Third Floor Studio by 747 Lofts
Interior
Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
2.0 star property
Downtown Chicago
Downtown Chicago Stay with Free In & Out Parking 3
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$536
HK$1,481 total
includes taxes & fees
6 Jan - 7 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space
Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$443
HK$1,178 total
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Studio Near UChicago
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 Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Rooms were clean. Easy check in. Front desk was welcoming. Very close to everything. We will book again. "
Yakshna 1-night trip
Posted 1 day ago
The Whitehall Hotel, BW Premier Collection

Find out more about Maywood

Search for holiday rentals in Maywood on Expedia! You can easily find your home rentals, villas, holiday apartments in Maywood using one of the methods below:

  • View our selection of featured holiday rentals in Maywood
  • Use the map to find apartments and other holiday homes in the Maywood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Maywood while they last

Look no further and take a look at our great range of rental properties in Maywood!

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 7 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 Michigan Avenue 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.