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

Maywood Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Maywood holiday rentals

Smart TV

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, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is HK$1,293
HK$2,515 total
includes taxes & fees
6 Jul - 7 Jul
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,192 reviews)
"Great location"
United States
JAVIER
The price is HK$1,366
HK$1,833 total
includes taxes & fees
5 Jul - 6 Jul
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (796 reviews)
"Great place to stay."
United States
Benedictine
The price is HK$2,031
HK$2,845 total
includes taxes & fees
21 Jun - 22 Jun
Kasa Magnificent Mile Chicago
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is HK$2,641
HK$5,648 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
TV, offices

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 reviews)
"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.
The price is HK$2,367
HK$4,667 total
includes taxes & fees
12 Jul - 13 Jul
River North Private Balcony With In and Out Parking
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (142 reviews)
"Perfect place to stay!"
United States
Anton
The price is HK$1,340
HK$1,534 total
includes taxes & fees
19 Jul - 20 Jul
The Gem Museum Suites
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (21 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is HK$4,036
HK$7,630 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 4BR Central Apartment w/ Skyline Views
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is HK$1,873
HK$5,359 total
includes taxes & fees
21 Jun - 22 Jun
Modern West Loop Gem-City Views & Prime Location 3
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is HK$1,356
HK$2,348 total
includes taxes & fees
21 Jul - 22 Jul
Chic Studio in the Heart of the Gold Coast
Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is HK$2,353
HK$4,597 total
includes taxes & fees
22 Jun - 23 Jun
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$1,424
HK$2,500 total
includes taxes & fees
22 Jun - 23 Jun
The Oak Park Loft
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is HK$1,411
HK$2,508 total
includes taxes & fees
24 Jun - 25 Jun
✽ Charming Cottage ✽ close to College/Town/Station
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (196 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is HK$1,799
HK$2,755 total
includes taxes & fees
21 Jun - 22 Jun
Kasa River North Chicago
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
"Great place to stay for our girls weekend. Very convenient to everything in the city! We had the second unit and just to know this is a walk up with about 40-45 stairs to get to the unit. "
United States
Dawn P.
The price is HK$1,505
HK$3,733 total
includes taxes & fees
3 Jul - 4 Jul
Beautiful Unit CHI in Prime River North - 2
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is HK$2,978
HK$6,045 total
includes taxes & fees
17 Jul - 18 Jul
South Loop Rooftop With In and Out Parking 2
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is HK$1,497
HK$3,159 total
includes taxes & fees
9 Jul - 10 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the location."
United States
Nicoll M.
The price is HK$2,704
HK$3,629 total
includes taxes & fees
21 Jun - 22 Jun
LIVN Millennium Park Downtown Chicago Superior 2 BR
Interior

870 1&2 - 2 Separate Suites in same building

870 1&2 - 2 Separate Suites in same building
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great spot in a great area"
United States
Jesse H.
The price is HK$3,840
HK$8,617 total
includes taxes & fees
3 Jul - 4 Jul
870 1&2 - 2 Separate Suites in same building
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (7 reviews)
"The parking situation is pretty rough. You have to park a half a mile away from the property. The room looks very luxurious in the pictures. However, once you get there, it does show some age and you can hear the other guest from above and below at all night not to mention that the city sounds are in full effect horns and traffic all night long and it’s difficult to get the room dark"
United States
Robert
The price is HK$3,252
HK$4,360 total
includes taxes & fees
24 Jun - 25 Jun
LIVN West Loop Chicago 2 BR City View
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (29 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is HK$1,160
HK$2,542 total
includes taxes & fees
21 Jun - 22 Jun
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

8/10 Good
"The only thing that would have made it excellent was if they had a pool/spa."
Diana 1-night trip
Posted 2 hours ago
Hyatt Regency O'Hare Chicago

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 8 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.