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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Maywood vacation 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 AED 545
AED 1,106 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, (1,195 reviews)
"Great location"
United States
JAVIER
The price is AED 614
AED 829 total
includes taxes & fees
6 Jul - 7 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, (797 reviews)
"Great place to stay."
United States
Benedictine
The price is AED 1,547
AED 2,032 total
includes taxes & fees
24 Jun - 25 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 AED 1,227
AED 2,629 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 AED 1,131
AED 2,219 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 AED 616
AED 705 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 AED 1,601
AED 3,155 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 AED 1,701
AED 3,676 total
includes taxes & fees
23 Jul - 24 Jul
Modern West Loop Gem-City Views & Prime Location 3
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is AED 577
AED 1,032 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.
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is AED 743
AED 1,258 total
includes taxes & fees
15 Jul - 16 Jul
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 AED 661
AED 1,176 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, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
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 AED 628
AED 1,641 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 AED 1,451
AED 2,910 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)
"Our stay was very comfortable. Communication was fantastic and super timely. The kitchen was well stocked. The house was very clean and spacious. Would definitely stay there again!"
United States
Erin B.
The price is AED 702
AED 1,473 total
includes taxes & fees
9 Jul - 10 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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 AED 1,679
AED 3,871 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 AED 746
AED 984 total
includes taxes & fees
29 Jun - 30 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 AED 552
AED 1,199 total
includes taxes & fees
24 Jun - 25 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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great location and clean/comfy"
Jessica 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

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 8 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 Michigan Avenue 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.